Middletown holiday rentals

We found 876 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Middletown that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and Wi-Fi. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Middletown

Showing deals for:18 Dec - 25 Dec

Basement - Full Kitchen, Pull out couch
Outdoor patio fireplace, patio heaters.
Pool
Interior
Exceptional
(57 reviews)

Resort style getaway w/pool, spa, game room & more

East Haddam

8% off
AU$11,238
for 7 nights, 1 home
AU$1,605 per night
includes taxes & fees
Resort style getaway w/pool, spa, game room & more
Interior
Exterior
Room
Dining
Exceptional
(67 reviews)

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Westbrook

8% off
AU$9,792
for 7 nights, 1 home
AU$1,399 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Exterior
Exterior
Exterior detail
Beach
Wonderful
(59 reviews)

2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT

Old Lyme

8% off
AU$3,542
for 7 nights, 1 cottage
AU$506 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Kitchen
Front of House
Living Room
Aerial view of back deck area
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
AU$6,768
for 7 nights, 1 home
AU$967 per night
includes taxes & fees
4 BED/2 BATH -PRIVATE BEACH: OLD COLONY
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Main Kitchen/Dining/Living Room
Exceptional
(9 reviews)

Luxury Beach House in Giants Neck Beach - Perfect for Large Families!

Niantic

8% off
AU$8,762
for 7 nights, 1 home
AU$1,252 per night
includes taxes & fees
Luxury Beach House in Giants Neck Beach - Perfect for Large Families!
Exterior
Terrace/patio
Private kitchen
Room
Exceptional
(33 reviews)

Updated cottage "Beriozka" on Cedar Lake

Chester

7% off
AU$2,269
for 7 nights, 1 cottage
AU$324 per night
includes taxes & fees
Updated cottage "Beriozka" on Cedar Lake
Interior
Dining
Terrace/patio
Private kitchen
Exceptional
(5 reviews)

Modern Family Retreat w/ Office & Fast WiFi

East Hartford

7% off
AU$5,953
for 7 nights, 1 home
AU$850 per night
includes taxes & fees
Modern Family Retreat w/ Office & Fast WiFi
Kitchen
Property grounds
Dining
Property grounds
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
AU$11,272
for 7 nights, 1 home
AU$1,610 per night
includes taxes & fees
Cornfield Point Cottage
Front of Historic Mansion B&B
Living area
Bedroom with 2 single Beds
Dining
Exceptional
(6 reviews)

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

Higganum

8% off
AU$2,496
for 7 nights, 1 room
AU$357 per night
includes taxes & fees
Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance
Dining
Living area
Exterior detail
Outdoor dining
Exceptional
(38 reviews)

Cottage near the beach

Niantic

7% off
AU$2,437
for 7 nights, 1 cottage
AU$348 per night
includes taxes & fees
Cottage near the beach
Outdoor dining
Dining
Exterior
Living area
Exceptional
(10 reviews)

Cheerful 3bd Cape yards from beach/ river access

Waterford

8% off
AU$5,099
for 7 nights, 1 home
AU$728 per night
includes taxes & fees
Cheerful 3bd Cape yards from beach/ river access
Interior
Beach
Living area
Room
Exceptional
(27 reviews)

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Niantic

11% off
AU$5,425
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS
Kitchen
Back deck
Living room, bathed in morning light
Private kitchen
Wonderful
(90 reviews)

Historic New England home ,Reunions Beach pass

Guilford

8% off
AU$5,647
for 7 nights, 1 home
AU$807 per night
includes taxes & fees
Historic New England home ,Reunions Beach pass
Dining
Property grounds
3 season porch with couch, 2 upholstered chairs and coffee table
Private kitchen
Exceptional
(13 reviews)

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

Higganum

16% off
AU$4,594
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Exterior
Dining
Pool
Terrace/patio
Exceptional
(7 reviews)

Private Home - Pool and Close to CT Shoreline Beaches

North Branford

17% off
AU$14,253
for 7 nights, 1 home
AU$2,036 per night
includes taxes & fees
Private Home - Pool and Close to CT Shoreline Beaches
Living area
Winter afternoon from the boathouse
Full chef's kitchen with new appliances
Ipe deck in the morning sun
Exceptional
(6 reviews)

Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet

Old Lyme

16% off
AU$8,319
for 7 nights, 1 home
AU$1,188 per night
includes taxes & fees
Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet
Room
Beach
Living area
Private kitchen
Exceptional
(32 reviews)

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

Clinton

11% off
AU$5,425
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Newly remodeled kitchen
Beautiful sun room for dining
family room
Private kitchen
Exceptional
(27 reviews)

Make Memories in Charming Hawk's Nest Beach!

Old Lyme

8% off
AU$3,533
for 7 nights, 1 home
AU$505 per night
includes taxes & fees
Make Memories in Charming Hawk's Nest Beach!
Room
Property grounds
Private kitchen
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Exceptional
(66 reviews)

Summer at the Haddam House

Haddam

8% off
AU$2,543
for 7 nights, 1 home
AU$363 per night
includes taxes & fees
Summer at the Haddam House
Interior
Exterior
Beach
Living area
Exceptional
(55 reviews)

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Old Lyme

8% off
AU$2,770
for 7 nights, 1 cottage
AU$396 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT
Living area
Dining
Exterior
Room
Exceptional
(47 reviews)

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

Westbrook

7% off
AU$4,436
for 7 nights, 1 home
AU$634 per night
includes taxes & fees
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Living Room
Dining Room
Queen Bedroom 1
Living Room
Excellent
(5 reviews)

2BR Apartment Near Wesleyan 102

Middletown

7% off
AU$2,166
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
2BR Apartment Near Wesleyan 102
Queen Bedroom 1
Stairwell
Living Room
Living Room
Wonderful
(7 reviews)

Private Apartment in Berlin

Berlin

7% off
AU$2,159
for 7 nights, 1 apartment
AU$308 per night
includes taxes & fees
Private Apartment in Berlin
Interior
Terrace/patio
Living area
Room
Exceptional
(10 reviews)

WeHa Penthouse w/ Private Deck

West Hartford

8% off
AU$1,742
for 7 nights, 1 home
AU$249 per night
includes taxes & fees
WeHa Penthouse w/ Private Deck

  • 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

The scenic area of Middletown awaits your stay

The area's entertainment and festivals are just some of the reasons to come on holiday to Middletown. Travellers to this scenic city praise the basketball games, university setting and riverfront. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Middletown

Do you want to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Middletown a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Brownstone Exploration & Discovery Park (0.9 mi / 1.5 km)
  • TPC River Highlands (4.8 mi / 7.8 km)
  • Powder Ridge Mountain Park and Resort (6.3 mi / 10.1 km)
  • Machimoodus State Park (10 mi / 16.1 km)
  • Chatfield Hollow State Park (13.9 mi / 22.3 km)
  • Mount Southington Ski Area (14.3 mi / 22.9 km)

Exploring the natural landscape of Middletown

Whether you're looking for fun outdoor activities or just want to take in the scenery, Middletown is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • General Mansfield House (0.3 mi / 0.5 km)
  • Lake Beseck Beach (5.4 mi / 8.7 km)
  • Dinosaur State Park (6.1 mi / 9.8 km)
  • Chatfield Hollow State Park (13.9 mi / 22.3 km)
  • Mortensen Riverfront Plaza (14 mi / 22.6 km)
  • West Hartford Reservoir (14.1 mi / 22.6 km)

Transport to and around Middletown

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 23.8 mi (38.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Hartford, CT (BDL-Bradley Intl.), which is 25.5 mi (41 km) away.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday rental?
When considering the best area to stay in Middletown, Connecticut, the downtown district stands out as an excellent choice for holiday rentals. This vibrant neighbourhood is known for its charming streets lined with historic buildings, offering a delightful mix of shops, restaurants, and cultural experiences. The atmosphere is both lively and welcoming, making it a great base for exploring the city.In downtown Middletown, you'll find easy access to attractions such as the beautiful Wadsworth Falls State Park, where visitors can enjoy scenic hiking trails and picturesque waterfalls. The nearby Connecticut River also provides opportunities for leisurely walks along the waterfront, where you can soak in the natural beauty of the area.Another appealing neighbourhood is the South End, which features a more residential feel while still being close to the city's amenities. This area is known for its tree-lined streets and proximity to parks, making it ideal for families or those looking for a quieter stay.Overall, Middletown boasts a variety of properties, with options ranging from cosy apartments to charming houses, ensuring that visitors can find the great accommodation to suit their needs.
Where are the best areas for renting a beach house in Middletown?
For renting a beach house in Middletown, Connecticut, the shoreline area along the Connecticut River and near the Long Island Sound is particularly appealing. The neighbourhoods of Westbrook and Old Saybrook, just a short drive from Middletown, offer lovely coastal rentals that provide easy access to sandy beaches and picturesque views of the water. Many properties in these areas come with desirable amenities such as spacious decks, outdoor grills, and well-equipped kitchens, making them great for family gatherings or a retreat with friends.In Westbrook, visitors can enjoy the quiet charm of the local beaches, with some houses boasting direct beach access or proximity to nature trails. The area around the Westbrook Town Beach features rentals that often include outdoor showers, private yards, and comfortable living spaces designed for relaxation after a day spent by the sea. Additionally, local shops and seafood restaurants nearby enhance the beach experience.Old Saybrook offers a slightly more upscale vibe, with beach houses that may feature amenities such as private pools, scenic gardens, and expansive views of the Long Island Sound. The historic charm of the town, combined with easy access to local attractions like the Katharine Hepburn Cultural Arts Centre, makes it an attractive destination for those seeking both beachside relaxation and cultural experiences.
Where are the best Middletown ski resort rentals?
For ski resort rentals near Middletown, Connecticut, the closest ski areas are located in the surrounding regions, particularly in areas like Cheshire and New Hartford, which are both approximately a 30 to 45-minute drive away. In Cheshire, travellers can find a range of charming cabins and lodges that offer cozy accommodations for families or groups. Many of these properties include amenities such as fully equipped kitchens, warm living rooms with fireplaces, and outdoor spaces for enjoying the winter scenery.In New Hartford, the ski resort features a variety of rental options, including ski-in/ski-out lodges that provide direct access to the slopes. Here, guests can expect modern conveniences like ski storage, boot warmers, and communal areas for socialising after a day on the mountain. The nearby towns also offer local dining options and shops, enhancing the overall experience for visitors.For those looking to explore beyond skiing, the scenic Litchfield Hills region nearby is ideal for winter hiking and snowshoeing, with various trails that cater to different skill levels.
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 about 44 available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or groups. Additionally, there are around 32 apartments scattered across the city, often located near local attractions and parks, providing a more compact living option with essential amenities like kitchen facilities and comfortable living areas. There are also several condos available, which usually offer a blend of privacy and shared facilities, suiting those who prefer a more communal living environment.
Are there any family house rentals in Middletown?
In Middletown, Connecticut, there are numerous family-friendly house rentals available, with around 11 properties to choose from. This charming city offers a variety of options suitable for families, often featuring spacious living areas and fully equipped kitchens, which are superb for preparing meals together. Many homes also come with outdoor spaces where children can play and enjoy the fresh air.Visitors will find that Middletown is conveniently located near attractions like the Kidcity Children's Museum, which provides interactive exhibits designed for young learners, and the scenic Wadsworth Falls State Park, ideal for hiking and picnicking. With various amenities, including Wi-Fi and laundry facilities, these homes ensure a comfortable stay while providing easy access to local parks, shops, and dining options.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This charming city, located along the Connecticut River, offers a mix of suburban comfort and outdoor recreation. Many of the rentals come equipped with amenities such as private swimming pools, outdoor seating areas, and hot tubs, providing an ideal setting for relaxation and leisure after a day of exploring the area.Travellers can expect spacious living areas, fully equipped kitchens, and comforts like air conditioning and Wi-Fi. Additionally, the proximity to local parks and the river makes it a great base for outdoor activities.
Are there pet-friendly house rentals in Middletown?
In Middletown, Connecticut, there are several pet-friendly house rentals available, suiting those travelling with furry companions. Many of these properties offer a range of amenities, including spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Some rentals may even feature additional conveniences such as laundry facilities and outdoor spaces for relaxation.The city itself is well-situated for exploring nearby parks and recreational areas, providing opportunities for walks and outdoor activities with pets. Notably, Wadsworth Falls State Park is a popular spot, featuring scenic trails and beautiful waterfalls, great for a day out with your dog. Additionally, the nearby Riverfront Park offers open spaces and walking paths along the Connecticut River, allowing for pleasant strolls in a picturesque setting.
Are there any remote work holiday rentals in Middletown?
In Middletown, Connecticut, there are a variety of remote work holiday rentals available, with approximately 72 options to choose from. Many of these properties come equipped with essential amenities for those looking to work remotely, such as reliable Wi-Fi and designated workspaces, ensuring a comfortable environment for productivity.The neighbourhood offers a mix of charming homes and modern apartments, often featuring fully equipped kitchens, spacious living areas, and comfortable bedrooms. Some rentals may even allow for events, providing flexibility for gatherings or meetings.Middletown itself is conveniently located near local attractions, including parks, shops, and restaurants, making it an appealing choice for both work and leisure. 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 rental amenities include well-equipped kitchens, making it convenient for guests to prepare their own meals. Onsite parking is also a common feature, ensuring easy access for those travelling with vehicles. Many rentals offer coffee and tea makers, which allow guests to enjoy a warm drink at any time. For those needing to work or study, desks are often available in the accommodations. Additionally, many properties boast decks or patios, providing lovely outdoor spaces for relaxation or enjoying the fresh air.
When is the best time to visit Middletown for a holiday rental?
The peak season in Middletown occurs from July to September, making it the most popular time for visitors eager to experience the warm summer months. This is a vibrant period where the town comes alive with outdoor activities, cultural events, and an inclusive setting superb for exploration. July, in particular, is a highlight, as visitors can enjoy the beautiful weather while taking part in local festivals and enjoying al fresco dining along the Connecticut River.During these summer months, temperatures typically range from the mid-teens to low 30s Celsius, providing an ideal climate for outdoor pursuits such as hiking, biking, and sightseeing. The nearby parks and historical sites, including the charming Main Street and the scenic Wadsworth Falls State Park, invite guests to immerse themselves in both nature and the rich local history.For those seeking a more budget-friendly option, consider planning your visit in October. This month offers a lovely transition into autumn, with mildly cool temperatures and stunning fall foliage that paints the landscape in vibrant hues. It's a wonderful time for quieter exploration, allowing visitors to appreciate the charm of Middletown without the crowds.Ultimately, the best time to book your holiday rental in Middletown hinges on your preferences for lively summer experiences or the serene beauty of fall.
What are the top attractions in Middletown?
In Middletown, Connecticut, visitors can discover a variety of attractions that highlight the area's rich history and natural beauty. The downtown area is vibrant, featuring charming shops, cafés, and restaurants, particularly along Main Street, where the local culture thrives. The scenic riverfront along the Connecticut River offers picturesque views and is great for leisurely walks or picnics.Just a short distance away, the Wadsworth Falls State Park provides opportunities for hiking and enjoying the outdoors, with beautiful waterfalls and trails that cater to various skill levels. For those interested in the arts, the nearby Middletown Arts District showcases local galleries and performance spaces, enhancing the cultural experience of the area.Additionally, the Wesleyan University campus is a popular point of interest, where visitors can explore the stunning architecture and possibly catch a performance or exhibition at the university's theatre or art galleries.
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