Middletown holiday rentals

We found 2,499 holiday rentals — enter your dates for availability

Discover a selection of 12 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:2 Oct - 9 Oct

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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. 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)
  • City Winery Hudson Valley (11.7 mi / 18.9 km)
  • Brotherhood Winery (13.5 mi / 21.7 km)
  • Mount Peter Ski Area (15.3 mi / 24.6 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)
  • Lake Louise Marie (14.2 mi / 22.9 km)
  • Sam's Point Preserve (15.7 mi / 25.3 km)
  • Ellenville Fault Ice Caves (16.1 mi / 26 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 home?
If you're thinking about a getaway to Middletown, Mount Hope is one of the most popular locations to stay. Whether you prefer a villa, cottage or another property type, you'll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Middletown?
The most desirable types of holiday homes in Middletown are houses. Searching for something different? Stayz offers a variety of options to match our guests' unique needs, so you'll see holiday properties in all sizes and shapes. The perfect fit is ready and waiting for you — find yours today.
How much does it cost to rent a holiday home in Middletown?
The average price for a holiday home in Middletown depends on a number of factors, such as time of year, length of stay and property type. Whether you're thinking about a sprawling villa with lots of bedrooms or a cosy cabin just for the two of you, just enter your dates of travel to view stays with exceptional value.
How much does it cost to rent a beach house in Middletown?
The average price for a holiday home near the beach in Middletown depends on when you're going and the style and size of property you're searching for. You can quickly and easily find prices on Stayz by entering your travel dates and destination. Then use our handy filter tool to choose the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Middletown?
Pack a travel bag and a bone for your canine companion because Middletown has eight holiday homes that roll out the welcome mat to pets. Let your furriest pal join in with the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your dates then check the "Pets allowed" filter box.
What are popular home amenities in Middletown?
Some of the most popular home amenities people search for in Middletown include nearby museums, a fireplace and mountain views. Whether you're on a trip with buddies, family or even pets, Stayz holiday homes provide the best amenities for beginning new traditions with the people who matter most.
Are there holiday homes in Middletown that welcome kids?
Middletown has eight family-friendly holiday homes. And discovering a stay that welcomes youngsters is easy with our "Properties good for families" filter. In addition to having the whole place to yourselves, you can also look forward to amenities and perks like bunk beds, kitchens and pools.
What are the top attractions for families in Middletown?
Keep the kids occupied at these awesome family-friendly attractions in Middletown:

  • Castle Fun Centre
  • Harness Racing Museum and Hall of Fame
  • Thomas Bull Memorial Park

Are there one-bedroom holiday homes in Middletown?
Yes, you'll find two one-bedroom properties in Middletown to pick from. A one-bedroom holiday property is a great option if it's only two of you or if you're flying solo. Add in more privacy, space and convenience than a standard hotel, and you're sure to have a trip to remember.
Can I find two-bedroom holiday homes in Middletown?
Gather your besties and enjoy a relaxing escape in one of the three two-bedroom holiday homes Middletown has to offer.
Are there holiday homes with WiFi in Middletown?
Middletown has three holiday homes with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to writing and sending emails, these Stayz homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Middletown?
Work out your travel dates and then use the filter tool to look for holiday homes with ac in Middletown on Stayz. With seven air-conditioned properties available, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Middletown?
The minimum age requirements can differ between properties on Stayz, so check the rules of the holiday home in Middletown you're considering. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Middletown for?
How long you can book a holiday home in Middletown differs according to the property. Simply enter your chosen travel dates to display a list of options offering extended stays. With many creature comforts like air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you're sure to find a terrific place to call your home away from home in Middletown.

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