Middletown holiday rentals: compare the best deals
10 2 reviews
Middletown
07/13 – 08/10
HK$2241/nighttotal: HK$62748 (28 )
2br Apartment Near Wesleyan 301
2 3
apartment , Middletown
This flat offers a prime location in Middletown's Washington Street Historic District, just 700 metres from Kidcity Children's Museum and a 1.3 kilometre walk to Harbor Park. This 88 square metre accommodation sleeps four guests and features two bedrooms, one bathroom, air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher, and on-site parking.
Middletown
07/08 – 07/09
HK$2853/nightfor 1 night
Cozy Family Home-sleeps 6 Near Wesleyan & Weddings
1 4
apartment , Middletown
This apartment is located in a secluded cul-de-sac in Middletown, offering privacy and easy access within 500 meters to Main Street's shops and eateries, Wesleyan University, and local wedding venues. This accommodation sleeps six and features two newly renovated bathrooms, a dining area for six, an eat-in kitchen, and a spacious backyard, with flexible sleeping arrangements including two queen beds, a twin bed, a futon, and a daybed.
Middletown
07/13 – 08/10
HK$4316/nighttotal: HK$120848 (28 )
Sunny Garden Home
1 3
apartment , Meriden
This Meriden flat is located in a quiet, family-friendly district, offering a peaceful retreat from the city's bustle. This two-bathroom flat accommodates four guests and features a kitchen, air conditioning, and garden access, providing a comfortable base for exploring local amenities.
8.8 94 reviews
Middletown
07/13 – 08/10
HK$1859/nighttotal: HK$52052 (28 )
Lovely 3 Bedroom Colonial Home
3 3
house , Middletown
This holiday home is located in Middletown, just 8.5km from Wesleyan University and within easy reach of Central Connecticut State University (17.7km) and the Wadsworth Atheneum (24.1km). It has consistently received excellent ratings for cleanliness, location and user experience. The property offers 127 square metres of space, comfortably accommodating up to 6 guests in 3 bedrooms and 2 bathrooms. Guests can enjoy a peaceful garden, a balcony, a fully equipped kitchen, laundry facilities, streaming services, free parking and Wi-Fi.
Middletown
07/08 – 07/09
HK$2695/nightfor 1 night
3 Br Apartment Near Wesleyan 201
1 4
apartment , Middletown
This three-bedroom flat in Middletown is located an eight-minute walk from Wesleyan University and 20 kilometres from Central Connecticut State University, offering convenient access to regional attractions including the Wadsworth Atheneum (25 kilometres), Bushnell Centre for Performing Arts (27 kilometres), Trinity College (22 kilometres), and Goodspeed Opera House (24 kilometres). This property offers 88 square metres of living space, accommodates up to eight guests, and includes a fully equipped kitchen with a dishwasher, on-site parking, and complimentary Wi-Fi.
Middletown
07/13 – 08/10
HK$1816/nighttotal: HK$50848 (28 )
Apartment In Middletown-wesleyan102
1 2
apartment , Middletown
This Middletown flat offers a prime location, a mere 640-metre walk from Wesleyan University and within 24 kilometres of Central Connecticut State University, Trinity College, and Goodspeed Opera House. This 88 square metre apartment accommodates up to five guests with two bedrooms, one bathroom, air conditioning, and on-site parking, boasting a fully equipped kitchen with a fridge and microwave, plus free Wi-Fi.
9.6 31 reviews
Middletown
07/13 – 08/10
HK$1149/nighttotal: HK$32172 (28 )
Fashionably Cozy Place
1 3
apartment , Meriden
This apartment is located in Meriden, Connecticut, just a short drive from Hubbard Park, Gouveia Vineyards, and Castle Craig, and is conveniently located 20 minutes from downtown Hartford, 1.5 hours from New York City, and 20 minutes from New Haven. The apartment has received very good user and location ratings, and an excellent cleanliness rating. This self-catering property has two bedrooms and can accommodate up to four guests. The apartment offers a fully equipped kitchen with a fridge, freezer, and microwave oven, as well as air conditioning, parking, and internet access.
9.5 103 reviews
Middletown
07/08 – 07/09
HK$2132/nightfor 1 night
59 Old Maids Lane Pool House
1 4
house , Glastonbury
This unique tiny house is situated on Old Maids Lane in Glastonbury, just a short distance from the Connecticut River and hiking trails, offering a peaceful and tranquil setting. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. The two-storey tiny house sleeps up to four guests and features a well-equipped kitchen, a combined washer/dryer, and a private bathroom. Guests can enjoy the shared pool, a stone patio, and a pergola, making it ideal for relaxing and enjoying the outdoors.
9.4 26 reviews
Middletown
07/13 – 08/10
HK$1477/nighttotal: HK$41356 (28 )
Spacious And Indulging
1 3
apartment , Meriden
This three-bedroom apartment is located on Wilcox Avenue in Meriden, just a short distance from the town centre and its attractions. The surrounding area is quiet and residential, offering a peaceful retreat from the hustle and bustle of the town. The apartment can accommodate up to seven guests and features a spacious living area, a well-equipped kitchen, and a large bathroom. It is perfect for families or groups of friends looking for a comfortable and convenient base to explore Meriden. Amenities include a fast internet connection, air conditioning, parking, and a modern kitchen with a fridge, freezer, and microwave.
9.3 3 reviews
Middletown
07/13 – 08/10
HK$861/nighttotal: HK$24108 (28 )
(King Bed) Close To Midstate
1 3
apartment , Meriden
This Meriden apartment, ideal for families, offers two bedrooms and one bathroom, comfortably sleeping five guests and includes a fully equipped kitchen, in-unit laundry, and a 60-inch flat-screen TV with streaming services. The property boasts a newly remodelled bathroom, hardwood floors, and smart locks, alongside the convenience of early check-in/check-out (fee applies), but its precise location within Meriden is unspecified.
8.2 9 reviews
Middletown
07/13 – 08/10
HK$1589/nighttotal: HK$44492 (28 )
2br Apartment Near Wesleyan 102
1 2
apartment , Middletown
This two-bedroom flat in Middletown is conveniently located a short distance from Wesleyan University, making it ideal for visitors to the university and business travellers. This pet-friendly apartment offers a welcoming home-away-from-home experience with a fully equipped kitchen, on-site laundry, and accommodation for up to four guests, with flexible stay options available.
9.3 9 reviews
Middletown
07/13 – 08/10
HK$866/nighttotal: HK$24248 (28 )
Quaint Studio Walkable To Downtown And Wesleyan
1 2
apartment , Middletown
This Middletown studio apartment is conveniently located 0.8km from Wesleyan University and 1.6km from Middletown's city centre. The self-contained unit, sleeping two, features a kitchenette with hotplate, microwave, fridge and kettle, a private shower room, and a double bed; guests can easily explore downtown Middletown's restaurants and shops.
Best family friendly Middletown holiday rentals
Among the 100 accommodations in Middletown, here are the 4 best family friendly rentals
9.6 5 reviews
Middletown
07/08 – 07/09
HK$2594/nightfor 1 night
“3br Home Near Wesleyan & Downtown Middletown
1 4
apartment , Middletown
This three-bedroom flat is located in a quiet district of Middletown, offering a peaceful retreat with convenient access to local amenities and family-friendly attractions. This accommodation for five guests includes internet, a kitchen, air conditioning, and parking, providing a comfortable base for exploring Middletown.
9.9 44 reviews
Middletown
07/13 – 08/10
HK$4241/nighttotal: HK$118748 (28 )
The Farmhouse Stay
1 3
apartment , Haddam
The Farmhouse Stay is situated in Haddam, just a short drive from the Connecticut River and the historic Haddam Meadows State Park, offering a peaceful setting surrounded by nature. The property has received excellent ratings for its cleanliness, location, and overall experience. The two-bedroom, two-bathroom house can comfortably accommodate up to six guests and features a well-equipped kitchen, laundry room, and a spacious garden. Guests can enjoy a range of activities, including hiking, kayaking, and exploring the nearby historic sites.
9.8 338 reviews
Middletown
07/08 – 07/09
HK$2672/nightfor 1 night
Historic Greek Revival Brick Home
1 4
apartment , Middletown
This charming first-floor apartment is located in Middletown's Downtown Village Historic District, just a short walk from Main Street, Wesleyan University, and the public library. The property has consistently received excellent ratings for location, cleanliness, and overall user experience. The apartment comfortably accommodates up to 6 guests, with two bedrooms and one bathroom, and features a spacious living area, a well-equipped kitchen, and a private outdoor space. Guests can enjoy a relaxing stay with amenities such as a dishwasher, laundry access, a garden with a patio and fire pit, and a convenient location within walking distance of local attractions.
9.7 254 reviews
Middletown
07/08 – 07/09
HK$2774/nightfor 1 night
Beautiful Sunny Apartment In Historic Village
1 4
apartment , Middletown
This charming apartment is located in Middletown's Downtown Village Historic District, just a short walk from Wesleyan University and the public library. The property has excellent user, location, and cleanliness ratings. The apartment is situated on the second floor of a beautifully preserved 1849 Greek Revival brick home and can comfortably accommodate up to six guests. Guests can enjoy a fully equipped kitchen, a relaxing living room with cable TV and Wi-Fi, and access to a private garden.
Best Middletown holiday rentals with parking
Middletown
07/13 – 08/10
HK$3602/nighttotal: HK$100856 (28 )
Historic Home 3 Miles To Middletown Main Street
6 3
house , Middletown
This historic dwelling in Middletown is situated 3 kilometres from Main Street, 3.4 kilometres from Wesleyan University and 24 kilometres from the Goodspeed Opera House. The property offers 545 square metres of living space with 6 bedrooms, 3 bathrooms, and can accommodate up to 23 guests, featuring a fully equipped kitchen, air conditioning, internet, and private parking.
8.8 3 reviews
Middletown
07/13 – 08/10
HK$2158/nighttotal: HK$60424 (28 )
#28- *Modern Bungalow*
2 3
apartment , New Britain
This New Britain holiday home is situated 0.5km from Central Connecticut State University, conveniently close to the Iwo Jima Survivors Memorial Park and New Britain Museum of American Art (both within 5km). The 88-square-metre property offers two bedrooms, one bathroom, sleeps five guests, and includes a fully equipped kitchen, laundry facilities, a balcony, and parking; nearby parks include Mill Pond Park and Batterson Park Pond.
Middletown
07/13 – 08/10
HK$2532/nighttotal: HK$70896 (28 )
3 Br Apartment Near Wesleyan 202
1 3
apartment , Middletown
This three-bedroom flat is located near Wesleyan University in Middletown, offering easy access to the university and the surrounding areas, with complimentary on-site parking and free WiFi. This 93 square meter residence features air conditioning, a fully equipped kitchen with a dishwasher and oven, and can accommodate up to eight guests, with towels and bed linen provided.
Middletown
07/08 – 07/09
HK$3538/nightfor 1 night
3 Br Apartment Near Wesleyan 201
3 4
apartment , Middletown
This Middletown flat is located in the Washington Street Historic District, a short walk from Wesleyan University and within easy reach of major cities. This 88 square meter residence accommodates up to six guests across three bedrooms, featuring a fully equipped kitchen, on-site laundry, and is conveniently situated near Artfarm, Dinosaur State Park, and Cromwell Meadows Wildlife Management Area.
Frequently asked questions about holiday rentals in Middletown
When is the best time to book a vacation rental in Middletown, CT?
The best time to book a vacation rental in Middletown is during the shoulder seasons, from April to May and September to October. The weather is still pleasant during these months, but the crowds are smaller and the prices are lower.
What are the best Airbnb and vacation rentals in Middletown?
What events or festivals should visitors check out in and around Middletown, CT?
Middletown hosts a variety of events throughout the year. The Middletown Arts Festival is a popular event in the summer, showcasing local artists and musicians. In the autumn, the Middletown Fall Festival features a parade, live music, and a craft fair. And if you're in town during the winter, be sure to check out the Middletown Holiday Festival, which features a tree lighting ceremony, carols, and Santa Claus.
What are the best budget-friendly activities in Middletown, CT?
Middletown has plenty of free and budget-friendly activities to offer. You can take a walk or bike ride along the scenic Connecticut River, visit the free exhibits at the Wesleyan University Art Museum, or explore the historic downtown area.
What are the best vacation rentals with a pool in Middletown?
What are the best restaurants with local dishes in Middletown, CT?
For a taste of Middletown's local cuisine, you should definitely check out the Silver Star Restaurant. They're known for their classic American dishes, including their famous burgers and fries. If you're looking for something a bit more upscale, the A Mano Restaurant is a great choice, with its focus on fresh, seasonal ingredients.
What are the best rentals for families and kids in Middletown?
What are the best walking or cycling routes in Middletown, CT?
The Mattabesett Trail is a popular walking and cycling route that runs through Middletown. It's a scenic trail that follows the Mattabesett River and offers beautiful views of the surrounding countryside. For a shorter, more urban walk, you can explore the downtown area and its historic streets.
What are the best rentals or Airbnbs with a jacuzzi in Middletown?
Are there pet-friendly attractions in Middletown, CT?
Many of Middletown's parks and gardens are pet-friendly. The Wadsworth Mansion allows well-behaved dogs on leashes in its gardens, and the Long Hill Estate and Gardens also welcomes furry friends. You can also find pet-friendly restaurants and cafes in the downtown area.
What are the benefits of choosing a vacation rental in Middletown, CT?
Vacation rentals in Middletown offer more space and privacy than hotels, often at a lower cost. They also provide access to kitchens and laundry facilities, which can be convenient for families or longer stays. You might also enjoy the unique character and charm of a home away from home.
What are the top sports attractions and facilities in Middletown, CT?
Middletown is home to several sports facilities, including the Wesleyan University athletic fields and the Middletown YMCA. The city also hosts a variety of sporting events, including high school football games and the annual Middletown Marathon.
Destinations nearby
Best Middletown holiday rentals with a balcony
Middletown
07/13 – 08/10
HK$3010/nighttotal: HK$84280 (28 )
3 Br Apartment Near Wesleyan 202
3 3
apartment , Middletown
This property is located in Middletown's Washington Street Historic District, a short distance from Wesleyan University and Wadsworth Mansion. This 93 square metre flat offers accommodation for up to six guests, featuring three bedrooms, a fully equipped kitchen with a dishwasher, and a balcony.
9.0 7 reviews
Middletown
07/13 – 08/10
HK$1857/nighttotal: HK$51996 (28 )
Private Apartment In Berlin
2 2
apartment , Berlin
This Berlin holiday home is situated 2.9km from New Britain Stadium and 4km from Putter's Paradise Mini Golf, offering easy access to Berlin Station (a 13-minute walk). The 111 square metre property sleeps four guests in two bedrooms and one bathroom, boasting amenities including a fully equipped kitchen, free Wi-Fi, a Smart TV, and on-site parking, plus a playground.
8.0 9 reviews
Middletown
07/13 – 08/10
HK$1568/nighttotal: HK$43904 (28 )
Fashionably Cozy Place
2 3
apartment , Meriden
This two-bedroom apartment is situated in Meriden, conveniently located 16 km from Wesleyan University, 22 km from Lake Compounce, and 22 km from Central Connecticut State University. The surrounding area is peaceful and offers easy access to attractions, making it a great base for exploring the region. This property has received excellent ratings for cleanliness and location, ensuring a comfortable and enjoyable stay. The 121 square metre apartment comfortably sleeps six guests and features a fully equipped kitchen with a fridge and microwave, as well as air conditioning, free Wi-Fi, and parking. It is ideal for families or groups looking for a self-contained accommodation with a range of amenities, and is perfect for exploring Meriden and its surroundings.
10 2 reviews
Middletown
06/27 – 07/04
HK$3883/nighttotal: HK$27181 (7 )
Cabin Deck House - Formidable Cabin In Laurel Island
4 2
cabin , East Hampton
The Cabin Deck House is located on Laurel Island, a peaceful retreat just 11 miles from Wesleyan University and the Goodspeed Opera House. This charming property has received excellent ratings for its location, cleanliness, and overall experience. The cabin offers four bedrooms, providing ample space for families or groups of friends. Guests can enjoy stunning lake views from the private terrace, relax in the garden, and prepare meals in the fully equipped kitchen, which includes a fridge and a toaster.
Best pet friendly Middletown holiday rentals
Among the 100 accommodations in Middletown, here are the 4 best pet friendly rentals
8.0 7 reviews
Middletown
07/13 – 08/10
HK$1597/nighttotal: HK$44716 (28 )
Spacious And Quiet
3 3
apartment , Meriden
This three-bedroom Meriden apartment, ideal for families or groups of up to six, is conveniently located within a 2.4km walk of MidState Medical Center and Westfield Meriden shopping centre, and within 3.2km of Cedar Park and Falcon Field. The self-catering flat offers free on-site parking, free Wi-Fi, a Smart TV, a fully equipped kitchen including oven, hob, microwave, fridge and coffee maker, and is situated in a smoke-free building.
Middletown
07/13 – 08/10
HK$2234/nighttotal: HK$62552 (28 )
2br Apartment Near Wesleyan 102
2 3
apartment , Middletown
This two-bedroom flat in Middletown offers convenient access, situated a 9-minute walk from Kidcity Children's Museum and an 11-minute walk from Van Vleck Observatory, with on-site parking provided. This 88 square metre residence accommodates up to four guests, featuring air conditioning, Wi-Fi, a television, and a fully equipped kitchen, with laundry facilities and proximity to Dinosaur State Park and Cromwell Commons Shopping Centre.
8.5 11 reviews
Middletown
07/08 – 07/09
HK$2362/nightfor 1 night
Private Apartment In Berlin
1 4
house , Berlin
This two-bedroom house in Berlin, Connecticut is located just 16 kilometres from Wesleyan University and 18 kilometres from the Bushnell Center for Performing Arts, offering easy access to both cultural and educational attractions. The property has received excellent ratings for its cleanliness, location, and overall user experience. The 111 square metre house can comfortably accommodate up to 9 guests and features a fully equipped kitchen, free Wi-Fi, a TV, air conditioning, and a private parking space. Guests can also enjoy a spa and the option to bring their pets along.
9.4 20 reviews
Middletown
07/08 – 07/09
HK$2759/nightfor 1 night
Stylish And Cozy 2
1 4
apartment , Meriden
This two-bedroom Airbnb is conveniently located on Cherry Street in Meriden, Connecticut, just a short distance from Hubbard Park, Gouveia Vineyards, and the historic Castle Craig. The property has received excellent ratings for cleanliness and user experience, with a very good location rating. The Airbnb is perfect for a family or group of four, with two bedrooms and a fully equipped kitchen. Guests can enjoy modern amenities such as air conditioning, Wi-Fi, and a washing machine, as well as parking and the option to bring pets.