Middletown holiday rentals

We found 2,470 holiday rentals — enter your dates for availability
Discover a selection of 11 homes and other holiday rentals in Middletown that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Middletown

Showing deals for:13 Nov - 20 Nov

Bedroom 1, double bed
Property grounds
Exterior
Sun-room with french doors
Exceptional
(37 reviews)

Waterfront property, perfect winter getaway, directly on the Willowemoc!

Livingston Manor

11% off
AU$2,335
for 7 nights, 1 cabin
AU$334 per night
includes taxes & fees
Waterfront property, perfect winter getaway, directly on the Willowemoc!
Private kitchen
Interior
Terrace/patio
Room
Exceptional
(10 reviews)

Mountain Brook Cabin w/ 4-bedroom in lovely Cornwall with Jacuzzi Tub and Sauna

Cornwall

11% off
AU$8,597
for 7 nights, 1 cabin
AU$1,228 per night
includes taxes & fees
Mountain Brook Cabin w/ 4-bedroom in lovely Cornwall with Jacuzzi Tub and Sauna
Kitchen
Family room
Family Room
Dining Room looking into living room
Exceptional
(25 reviews)

Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre

Big Indian

8% off
AU$8,367
for 7 nights, 1 chalet
AU$1,195 per night
includes taxes & fees
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Pool
Interior
Living area
Indoor spa tub
Exceptional
(41 reviews)

Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!

Monticello

7% off
AU$6,337
for 7 nights, 1 villa
AU$905 per night
includes taxes & fees
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!
Exterior
Pool
Private kitchen
Exterior detail
Exceptional
(83 reviews)

Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool

Damascus

8% off
AU$5,604
for 7 nights, 1 home
AU$801 per night
includes taxes & fees
Private Hilltop Getaway with Hot Tub & Saltwater Heated Pool
Main entrance.
Two ovens, two refrigerators, plate warmer & an enormous butcher block counter.
Open kitchen that leads to a living area with fireplace.
Living area with wood burning fireplace,
Exceptional
(48 reviews)

Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views

High Falls

8% off
AU$11,537
for 7 nights, 1 home
AU$1,648 per night
includes taxes & fees
Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views
The main living area showing living room, dining area and kitchen.
The view as you enter the front door.
Enjoy the peaceful setting and the ever changing lake views.
Peaceful & Quiet Winter Retreat. Enjoy a warm fire and view the iced over lake.
Exceptional
(204 reviews)

Relaxing Lakefront, Very Clean. Great for Families.

Bethel

9% off
AU$4,178
for 7 nights, 1 home
AU$597 per night
includes taxes & fees
Relaxing Lakefront, Very Clean. Great for Families.
Exterior
Terrace/patio
Interior
Private kitchen
Exceptional
(26 reviews)

Private log cabin nestled at the base of a secluded wooded area

Yulan

8% off
AU$5,375
for 7 nights, 1 home
AU$768 per night
includes taxes & fees
Private log cabin nestled at the base of a secluded wooded area
A Special Place for Your Special Times! 4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
Dining
A cozy bedroom boasts a unique charm with its stone wall and wide plank flooring. Queen size bed with luxury linens you'll find it hard to leave. For your comfort we installed a MiniSplit system for heating and AC. Creating warm ambiance to enjoy.
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
Exceptional
(25 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
AU$5,665
for 7 nights, 1 home
AU$809 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Winter beauty
Breathtaking View, Situated on Orange Lake
Front of house. Lake in back.
Open floor kitchen, LR, and DR, with panoramic view of lake.
Exceptional
(328 reviews)

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh

8% off
AU$5,799
for 7 nights, 1 home
AU$828 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Kitchen, fully furnished with dishes, utensils, cookware and wine glasses.
Grey Towers, Pinchot home open to the Public,operated by Nat. Forest Service
Main Cabin, side view showing large deck,closed in porch,& picnic area
furnished closed in porch overlooking the cascading stream & swimming hole.
Exceptional
(41 reviews)

Creekside Knotty Pine 1930s Lodge on 575 Acre Forest Preserve

Milford

8% off
AU$3,449
for 7 nights, 1 room
AU$493 per night
includes taxes & fees
Creekside Knotty Pine 1930s Lodge on 575 Acre Forest Preserve
Interior
Exterior
Dining
Terrace/patio
Exceptional
(9 reviews)

Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road

High Falls

16% off
AU$6,865
for 7 nights, 1 home
AU$981 per night
includes taxes & fees
Mohonk's Peaceful 5BR-3BA~Jacuzzi~Huge Deck~Right On Coxing Kill~ Private Road
Property grounds
Exterior
Interior
Interior
Exceptional
(46 reviews)

Cosy lakefront cottage in Hudson Valley

Walden

7% off
AU$2,377
for 7 nights, 1 cottage
AU$340 per night
includes taxes & fees
Cosy lakefront cottage in Hudson Valley
Living room through Mahogany pocket doors
View of the dining room
Walk way to back yard from side of the house
Hallway with pocket doors on main floor
Exceptional
(16 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

21% off
AU$7,908
for 7 nights, 1 home
AU$1,130 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
Terrace/patio
Living area
Private kitchen
Interior
Exceptional
(13 reviews)

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen

8% off
AU$1,925
for 7 nights, 1 cottage
AU$275 per night
includes taxes & fees
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Heated pool open from Memorial Day Weekend thru the end of September
Hot tub on the deck and open year round
Dining area
Kitchen
Excellent
(13 reviews)

Casa Nera | Heated Pool • Hot Tub • Ski • Golf

Swan Lake

15% off
AU$4,610
for 7 nights, 1 home
AU$659 per night
includes taxes & fees
Casa Nera | Heated Pool • Hot Tub • Ski • Golf
Living area
Private kitchen
Dining
Interior
Exceptional
(8 reviews)

Modern home w/creek view, steps to town & mountain

Beacon

8% off
AU$8,937
for 7 nights, 1 home
AU$1,277 per night
includes taxes & fees
Modern home w/creek view, steps to town & mountain
View of valley and lush evergreens. Queen bed. Spacious closet
Whip up delicious meals in the spacious, bright kitchen with ample counter space
Settle into the many comfy seats in the Family Room.
Comfortably seats 8 and also doubles as a large board game table.
Exceptional
(38 reviews)

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland

8% off
AU$6,143
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
Interior
Exterior
Pool
Living area
Exceptional
(6 reviews)

Luxe, Secluded Catskill Lodge Heated Pool, Hot Tub

Ellenville

8% off
AU$10,943
for 7 nights, 1 home
AU$1,563 per night
includes taxes & fees
Luxe, Secluded Catskill Lodge Heated Pool, Hot Tub
Living Room with Fire Place
View from Master Suite
Fully-Stocked Kitchen
View from Master Suite
Exceptional
(166 reviews)

Large Lake House Property Your Family And Friends Will Love Staying At!

Greenwood Lake

8% off
AU$4,989
for 7 nights, 1 home
AU$713 per night
includes taxes & fees
Large Lake House Property Your Family And Friends Will Love Staying At!
Dining
Living area
Living area
Exterior
Exceptional
(22 reviews)

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

Accord

6% off
AU$2,694
for 7 nights, 1 cottage
AU$385 per night
includes taxes & fees
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Outdoor fire pit with comfy chairs
Dining table with 8 chairs
Kitchen island
Room
Exceptional
(11 reviews)

Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.

Narrowsburg

11% off
AU$2,822
for 7 nights, 1 home
AU$403 per night
includes taxes & fees
Private vollyball court: 5-Acre Haven with AC close to Bethel Woods.
Interior
Room
Interior
Property grounds
Exceptional
(84 reviews)

for the creative spirit, swimming dock on pond, horses to pet, Fire pit

Ulster Park

8% off
AU$3,251
for 7 nights, 1 home
AU$464 per night
includes taxes & fees
for the creative spirit, swimming dock on pond, horses to pet, Fire pit
Private kitchen
Exterior
Room
Property grounds
Exceptional
(8 reviews)

Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8

Livingston Manor

8% off
AU$3,054
for 7 nights, 1 home
AU$436 per night
includes taxes & fees
Private 5-Acre Farmhouse Retreat - Bethel Woods 25 mins - Sleeps 8

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Middletown

  • Urban park retreats: Enjoy scenic parks and lakes offering perfect spots for leisurely strolls and family picnics.
  • Cultural charm: Explore local arts and cultural landmarks that reflect the welcoming community spirit.
  • Vibrant downtown: Wander through a lively downtown area with diverse shops and eateries.
  • Outdoor adventures: Partake in active outings amidst nearby nature and state parks.
  • Relaxing stays: Unwind in comfortable, generic accommodations that complement your city exploration.

Popular types of accommodation in Middletown

Welcome to Middletown, New York, a charming city that offers a delightful mix of attractions and experiences for every traveller. Explore the scenic beauty of local parks, indulge in vibrant arts, and savour delicious cuisine. For your stay, consider popular options such as private holiday homes, condos, and cabins, ensuring you find the perfect place to unwind after a day of discovery. Enjoy the warmth and hospitality of Middletown as you make lasting memories.

  • Private Holiday Homes: Experience the charm of an exclusive dwelling, offering privacy and comfort, making it the top choice in Middletown.
  • Condos: Enjoy modernity and efficiency in a well-appointed condo, a preferred selection for a sophisticated stay.
  • Cabins: Reconnect with nature in a cosy cabin, ideal for a rustic retreat in the countryside.
  • Cottages: Delight in a quaint cottage, perfect for a picturesque and intimate holiday experience.
  • Apartments: Relax in a stylish apartment, offering convenience and urban flair for your Middletown visit.**

Top attractions in and around Middletown

Middletown, New York offers an engaging urban experience for families and visitors seeking both culture and outdoor adventures. Explore the city's parks, lakes, and national state parks, where urban charm meets the beauty of nature. Whether you’re interested in leisurely strolls or active outings, Middletown’s attractions promise a delightful blend of city-themed entertainment and scenic landscapes.

  • Neversink River: A river with captivating outdoor and scenic vibes, situated 21km away from Middletown.
  • Stone Beach: A beach exuding classic seaside charm, located 16km from Middletown.
  • Orange County Fair Speedway: A motor racing venue within Middletown, offering a thrilling blend of sports and adventure.

Things to do recommended for couples

Searching for a romantic getaway in Middletown? Enjoy a leisurely stroll through the serene parks, savour a candlelit dinner at a local bistro, or unwind with a wine tasting at nearby vineyards. Each experience promises to create lasting memories for you and your partner.

Things to do recommended for families

Families visiting Middletown, New York, can enjoy the charm of local attractions, including kid-friendly parks, interactive museums, and delightful eateries, ensuring a memorable holiday experience for all ages.

Things to do recommended for groups

Experience the thrill of the Orange County Fair Speedway for motor racing, or embark on an adventure at Zoom Ziplines, just 29km away. For more racing excitement, visit Monticello Motor Club, located 31km from Middletown, perfect for adrenaline-seeking groups.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Middletown

If you are travelling with a group, family, pets, or seeking extended stays, be sure to set your priorities when filtering your options. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Middletown with a group: Think about how many bedrooms you require, as well as amenities like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and much more on Stayz.
  • Traveling to Middletown with young kids: Traveling with young children can present its challenges. Ensuring their comfort and safety, as well as access to age-appropriate amenities like a private swimming pool, is essential. It is also wise to consider how close you are to attractions that are suitable for families.
  • Taking your pets with you to Middletown: For many families, a holiday wouldn't be the same without their furry companion by their side. If this resonates with you, we invite you to explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Middletown: If you're seeking holiday lets with special offers for month-long or extended stays, you've come to the right place. With the appropriate filter, you can effortlessly locate and secure savings on monthly rentals. You might also consider including a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in and around Middletown

Middletown, New York, offers a delightful blend of family-friendly attractions and vibrant city life. Visitors can enjoy local parks and recreational areas, perfect for outdoor activities, while the charming downtown area features a variety of shops and eateries. The welcoming atmosphere is complemented by friendly locals, making it an ideal destination for families and those seeking entertainment. Whether you're exploring cultural landmarks or simply soaking up the community vibe, Middletown promises an enjoyable holiday experience.

  • Goshen: Goshen is a vibrant city located 10km from Middletown, offering a family-friendly, entertainment-themed, and urban experience. Visitors can enjoy a range of activities including a resort, shopping mall centre, and shopping centre. The area is celebrated for its landmark attractions such as a theme park, tourist precinct, and a charming square, all contributing to a dynamic travel experience that mixes modern amenities with local culture.
  • Mount Hope: Nestled within the vicinity of Middletown, Mount Hope is a picturesque village that invites travellers seeking an outdoor, adventure, and family experience. Its surrounding attractions include a water park, adventure activities, and a ski field, while its local landmarks feature a serene lake, a theme park, and a waterpark. This destination is perfect for those who relish outdoor pursuits and scenic explorations.
  • Warwick: Warwick is an engaging city situated 21km from Middletown. It is renowned for its outdoor, adventure, and ski experiences. The city offers diverse recreational opportunities with activities such as skiing, visits to ski fields, and leisurely explorations of recreational areas. Among its local attractions are a picturesque lake, a majestic mountain, and a lively theme park, making it an appealing destination for those seeking both adventure and natural beauty.

Best time to go to Middletown

If you're planning a trip to Middletown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January26.8°F (-2.9°C)Light RainMostly SunnySlightly LowAverage
February28.6°F (-1.9°C)Light RainMostly CloudyAverageSlightly Low
March36.1°F (2.3°C)Light RainMostly CloudyAverageSlightly Low
April47.5°F (8.6°C)Light RainMostly SunnySlightly HighSlightly Low
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnySlightly HighAverage
July72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
August70.5°F (21.4°C)Light RainMostly SunnyAverageSlightly High
September63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
October52.7°F (11.5°C)Light RainMostly SunnyAverageAverage
November40.6°F (4.8°C)Light RainMostly SunnySlightly LowAverage
December32.7°F (0.4°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Stayz is a breeze

Looking to cut costs on your next journey? Consider keeping your travel dates flexible, as prices do vary. Furthermore, opting for a longer stay can often lead to substantial savings. To find the ideal Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's Trip Board offers an easy-to-use platform for planning your journeys, allowing you to start new trips, resume previous ones, or organise your existing plans. You'll discover your saved or booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Head to the friendly city of Middletown

Enjoy the area's churches, architecture and festivals with a rental holiday home in Middletown. This welcoming city attracts visitors thanks to its shopping and restaurants. LEGOLAND® New York and Woodbury Common Premium Outlets are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Middletown

Are you searching for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Middletown has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® New York (7.5 mi / 12 km)
  • Goshen Historic Track (6.1 mi / 9.8 km)
  • Warwick Valley Winery and Distillery (10.7 mi / 17.2 km)
  • Brotherhood Winery (13.5 mi / 21.7 km)
  • Mount Peter Ski Area (15.3 mi / 24.6 km)
  • Holiday Mountain Ski and Fun Park (15.8 mi / 25.4 km)

Exploring the natural features in Middletown

Whether you're an adventurous traveller or just want to appreciate the scenery, Middletown is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Orange County Arboretum (8.1 mi / 13.1 km)
  • The Rock Sports Complex (10.3 mi / 16.5 km)
  • Neversink River (13.4 mi / 21.6 km)
  • Sam's Point Preserve (15.7 mi / 25.3 km)
  • Arrow Park Lake and Lodge (16.9 mi / 27.2 km)
  • Greenwood Lake (18.7 mi / 30.1 km)

Travelling to and around Middletown

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 17.8 mi (28.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday rental?
When considering a holiday rental in Middletown, New York, the downtown area is an excellent choice. This vibrant neighbourhood offers a variety of properties, from charming apartments to spacious houses, suiting different preferences and group sizes. Staying downtown puts you within walking distance of some delightful attractions, such as the Paramount Theatre, which hosts a range of performances and events, and the nearby Galleria at Crystal Run, a popular shopping destination with numerous dining options.Another appealing area is the scenic Wallkill Valley, known for its picturesque views and outdoor activities. This neighbourhood features a selection of holiday rentals, great for those seeking a more tranquil escape. The nearby Wallkill River offers opportunities for kayaking and fishing, while the beautiful hiking trails in the region invite nature lovers to explore the stunning surroundings.
Where are the best Middletown ski resort rentals?
For skiing near Middletown, New York, the nearest ski areas are located in the nearby Catskill Mountains, specifically around resorts such as Mountain Creek and Belleayre. For holiday rentals, travellers should consider the quaint towns of Warwick and Vernon, which provide convenient access to these ski resorts.In Warwick, visitors can find charming cabins and modern chalets that often include amenities like hot tubs, fireplaces, and expansive decks superb for après-ski relaxation. Many properties in this area also feature fully equipped kitchens, allowing guests to prepare their own meals after a day on the slopes.In Vernon, you can explore cozy lodges and family-friendly hotels that cater to various group sizes, with features like game rooms and proximity to local shops and dining options. Some rentals even offer stunning views of the surrounding mountains, enhancing the overall experience.The region around Middletown is not only great for skiing but also for outdoor enthusiasts, with opportunities for hiking and exploring in the warmer months. Properties in these towns often provide easy access to nature trails and scenic spots, making them ideal for year-round getaways.
What is the most popular type of holiday rental accomodation in Middletown?
In Middletown, holiday houses are the most popular type of holiday rental, with around 32 available across the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many also offer outdoor spaces for relaxation and gatherings. Additionally, there are approximately 24 campsites for those looking for a more adventurous stay, providing a great experience amidst nature. Cottages are another option, with about 12 available, typically offering a quaint and cosy atmosphere. While cabins and villas are less common, several can still be found, appealing to those seeking a rustic or luxurious retreat.
Are there any family house rentals in Middletown?
In Middletown, New York, there are some family-friendly house rentals available, with around 14 options to choose from. Visitors can find accommodations in various neighbourhoods, offering spacious living areas ideal for gatherings and comfortable family stays. Many properties come equipped with full kitchens, allowing for easy meal preparation, as well as amenities such as outdoor spaces where children can play.The town is conveniently located near attractions like the Wallkill River National Wildlife Refuge, which is superb for outdoor activities such as hiking and birdwatching. Families can also explore local parks and play areas that cater to children of all ages.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming town, located in the scenic Hudson Valley, provides a variety of options for travellers seeking a relaxing getaway. Many properties in the area come equipped with private pools and hot tubs, superb for unwinding after a day of exploring.Visitors can expect amenities such as spacious outdoor areas, fully equipped kitchens for home-cooked meals, and comfortable living spaces designed for families or groups.
Are there pet-friendly house rentals in Middletown?
In Middletown, New York, there are ten pet-friendly house rentals available, providing a variety of options for travellers with furry companions. Many of these properties feature comfortable amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces where pets can roam. The rentals often come with essentials like Wi-Fi, air conditioning, and laundry facilities, ensuring a convenient stay for families or groups.The surrounding area offers several parks that are superb for enjoying time outdoors with pets. For example, the nearby Fancher-Davidge Park features walking trails and open spaces, allowing for leisurely strolls and playtime. Additionally, the scenic Wallkill River provides opportunities for walking along the riverbanks, making it a delightful spot for pet owners.
Are there any remote work holiday rentals in Middletown?
In Middletown, New York, there are around 60 holiday rentals available that are suitable for remote work. This charming city offers a range of accommodations equipped with essential amenities for a productive stay. Many properties feature free Wi-Fi, ensuring that guests can stay connected, and are designed with comfortable workspaces or desks in the rooms.The area also boasts numerous points of interest, such as the scenic parks and outdoor spaces ideal for taking breaks or enjoying fresh air during work hours. Additionally, the proximity to local cafes and restaurants adds convenience for meals or a change of scenery from the home office. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Middletown?
In Middletown, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the fresh air. Additionally, pet-friendly options are available, permitting guests to bring their furry companions along, while some rentals accommodate service animals. Onsite parking is another amenity commonly found, ensuring guests have convenient access to their vehicles.
When is the best time to visit Middletown for a holiday rental?
The best time to visit Middletown for a holiday rental is during the peak season from June to August. This vibrant period attracts families and outdoor enthusiasts looking to enjoy the warm summer weather. With temperatures ranging from 20 to 30 degrees Celsius, it's ideal for exploring the scenic beauty of the Hudson Valley, participating in outdoor activities, and enjoying local events.July is particularly popular, offering a lively option filled with festivals, farmers' markets, and opportunities for hiking in the nearby Catskill Mountains. Visitors can experience firsthand the rich cultural scene, dine at local eateries, and relish the charm of Middletown's historic downtown.For those seeking a more budget-friendly experience, consider visiting in December. While this falls outside the main tourist season, it offers a unique opportunity to enjoy the festive atmosphere, including holiday decorations and events that create a warm and welcoming environment.Ultimately, the best time to book your holiday rental in Middletown hinges on whether you prefer the bustling summer activities or the quieter, cosy charm of winter festivities.
What are the top attractions in Middletown?
Middletown, New York, offers a variety of attractions that highlight its charm and natural beauty. One of the main draws is the Hudson Valley, which surrounds the area and provides stunning landscapes, great for outdoor activities such as hiking and biking. Nearby, the scenic Wawayanda State Park features numerous trails and a lovely lake for swimming and picnicking.In the heart of Middletown, visitors can explore the vibrant downtown area, which boasts a mix of shops, restaurants, and the historic Paramount Theatre, known for hosting a range of performances and events. The nearby Galleria at Crystal Run is a popular shopping destination with various retail outlets and dining options.For those interested in history, the Orange County Fairgrounds often hosts events and fairs throughout the year, while the nearby city of Newburgh, just a short drive away, offers historic sites and beautiful riverfront parks along the Hudson River.
Are all fees included in the Middletown holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Middletown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Middletown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Middletown holiday homes?
You can find great discounts on holiday homes in Middletown on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Middletown holiday home booking on Stayz?
To find Middletown holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Middletown?
A long-stay holiday home in Middletown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Middletown holiday home?
Book your Middletown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middletown?
Prices for holiday homes in Middletown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Middletown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas