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Best Vacation rentals and Airbnb offers in Middletown, CT
Middletown, CT
07/13 – 08/10
$299/nighttotal: $8372 (28 )
Simple Comfort And Tranquility
1 3
apartment , New Britain
This New Britain condo is a 7-minute walk from Walnut Hill Park and a 15-minute walk from the New Britain Museum of American Art. This rental offers Wi-Fi, a full kitchen with an oven and refrigerator, air conditioning, on-site laundry, and covered parking, with nearby attractions including Dinosaur State Park and the Xfinity Theatre.
Middletown, CT
07/13 – 08/10
$280/nighttotal: $7840 (28 )
2br Apartment Near Wesleyan 102
2 3
apartment , Middletown
This 2-bedroom, 1-bathroom apartment in Middletown offers 950 square feet of living space and accommodates up to 4 guests, located a 9-minute walk from Kidcity Children's Museum and an 11-minute walk from Van Vleck Observatory. This pet-friendly rental includes on-site parking, air conditioning, a fully equipped kitchen with a microwave and fridge, Wi-Fi, and an in-unit washer and dryer, providing convenient access to local attractions.
9.8 4 reviews
Middletown, CT
07/13 – 08/10
$154/nighttotal: $4312 (28 )
Chic With Recliner At Webster Hill Suite 1w Request Xtra Bed
1 2
apartment , New Britain
Webster Hill Suites, a one-bedroom apartment in New Britain, Connecticut, is located 2.6 miles from Central Connecticut State University and within a 10-12 mile radius of attractions like the Mark Twain House & Museum and Elizabeth Park. This 640-square-foot unit sleeps four guests and features a fully equipped kitchen, air conditioning, parking, outdoor seating, and offers paid airport shuttle service to Bradley International Airport, plus nearby opportunities for skiing and fishing.
9.6 5 reviews
Middletown, CT
07/08 – 07/09
$331/nightfor 1 night
“3br Home Near Wesleyan & Downtown Middletown
1 4
apartment , Middletown
This 3-bedroom, 1-bathroom condo in Middletown is located in a quiet district, offering a peaceful retreat for up to 5 guests. The residence includes internet, a kitchen, air conditioning, and parking, perfect for a relaxing family getaway.
9.4 26 reviews
Middletown, CT
07/08 – 07/09
$390/nightfor 1 night
Spacious And Indulging
1 4
apartment , Meriden
This apartment is located on Wilcox Avenue in Meriden, Connecticut, within easy walking distance of downtown and the Meriden Green. The surrounding area offers a mix of residential and commercial spaces, with easy access to local attractions, restaurants, and shops. The apartment is a three-bedroom unit that can comfortably accommodate up to seven guests. It features a spacious kitchen with a fridge, freezer, and microwave oven, as well as a comfortable living room with a smart TV.
9.7 254 reviews
Middletown, CT
07/08 – 07/09
$354/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 two blocks from Wesleyan University and across the street from the public library. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience. The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. The apartment provides modern amenities, including a fully equipped kitchen, air conditioning, a backyard with a grill, and free Wi-Fi.
9.0 44 reviews
Middletown, CT
07/13 – 08/10
$181/nighttotal: $5068 (28 )
Private Apt In Middletown-wesleyan 101
1 3
apartment , Middletown
This apartment is located in Middletown, just a short distance from Wesleyan University, making it a convenient choice for visitors attending events or visiting students. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience. The apartment offers a comfortable and spacious living space, perfect for accommodating up to 4 guests. The apartment is equipped with modern amenities, including a fully equipped kitchen, in-unit laundry, and a versatile loft space with a queen bed and a convertible couch.
8.3 6 reviews
Middletown, CT
07/13 – 08/10
$215/nighttotal: $6020 (28 )
2br Apartment Near Wesleyan 301
1 3
apartment , Middletown
This two-bedroom, one-bathroom rental unit is located in Middletown, a short distance from Wesleyan University. This pet-friendly apartment offers on-site parking, a fully equipped kitchen with a fridge, microwave, and dishwasher, and accommodates up to four guests.
Middletown, CT
06/27 – 07/04
$356/nighttotal: $2492 (7 )
Spacious 5-bedroom Family Home
1 2
apartment , New Britain
This New Britain apartment is located 22 miles from Bradley International Airport. This one-bedroom unit offers two bathrooms, a fully equipped kitchen, complimentary WiFi, and air conditioning, accommodating up to 19 guests with free private parking.
Middletown, CT
07/13 – 08/10
$379/nighttotal: $10612 (28 )
3 Br Apartment Near Wesleyan 202
3 2
apartment , Middletown
This 3-bedroom, 1-bathroom rental unit is located in Middletown's Washington Street Historic District, a short walk from Wesleyan University and Wadsworth Mansion. This 1000 square foot residence accommodates up to 6 guests and features a full kitchen, air conditioning, a porch, and is pet-friendly for an additional fee.
9.3 3 reviews
Middletown, CT
07/13 – 08/10
$110/nighttotal: $3080 (28 )
(King Bed) Close To Midstate
1 3
apartment , Meriden
This Meriden apartment rental sleeps five guests in two bedrooms and one bathroom, boasting a remodeled bathroom and new flooring throughout. The unit features a 60-inch flat-screen TV, in-unit laundry, a king-size Tempur-Pedic bed, and smart locks; early check-in/check-out is available for a fee.
Middletown, CT
07/13 – 08/10
$561/nighttotal: $15708 (28 )
Serene 3-bedroom House With Ac In Charming Berlin
3 3
apartment , Berlin
This Berlin apartment is located a short distance from the Barnes Museum and Iwo Jima Survivors Memorial Park, offering a local experience near family-friendly attractions like the New Britain Youth Museum. This 3-bedroom, 3-bathroom lodging accommodates up to 6 guests and includes internet, air conditioning, heating, an iron, and a hair dryer, with a 11:00 AM check-out time.
Top Vacation Rentals for Families in Middletown, CT
These kid-friendly vacation rentals in Middletown, CT keep you close to top city attractions for a stress-free family vacation.
9.8 27 reviews
Middletown, CT
07/08 – 07/09
$1027/nightfor 1 night
New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown.
4 4
apartment , Durham
This Durham vacation home is conveniently located near Millers Pond State Park (1.4 miles) and within 6 miles of Ron McCutcheon Park, Tri-Mountain State Park, Lyman Orchards, and Lyman Meadow Golf Club. This spacious four-bedroom house, sleeping up to eight guests, features a fully equipped kitchen, a fireplace, barbecue grills, and a terrace—perfect for families seeking outdoor recreation near Durham's parks and orchards.
9.9 44 reviews
Middletown, CT
07/13 – 08/10
$541/nighttotal: $15148 (28 )
The Farmhouse Stay
1 3
apartment , Haddam
The Farmhouse Stay is a short distance from the Connecticut River and historic Haddam landmarks, offering a peaceful retreat on 15 acres. It has excellent user, location, and cleanliness ratings. This two-bedroom, two-bathroom home comfortably sleeps six guests. The farmhouse provides a fully equipped kitchen, a garden, parking, air conditioning, and internet access.
8.8 94 reviews
Middletown, CT
07/13 – 08/10
$267/nighttotal: $7476 (28 )
Lovely 3 Bedroom Colonial Home
3 3
house , Middletown
This 3-bedroom house is conveniently located in Middletown, just a short drive from Wesleyan University and within easy reach of Hartford's cultural attractions. The property has consistently received excellent ratings for cleanliness, location, and overall user experience. The 1370 square foot house comfortably accommodates up to 6 guests. Amenities include a fully equipped kitchen, a private garden and balcony, free parking, and Wi-Fi, making it an ideal choice for families or groups of friends.
8.0 7 reviews
Middletown, CT
07/13 – 08/10
$206/nighttotal: $5768 (28 )
Spacious And Quiet
3 3
apartment , Meriden
This Meriden apartment rental is conveniently located within a 15-minute walk of MidState Medical Center and Westfield Meriden mall, near Cedar Park and Falcon Field. The three-bedroom, one-bathroom unit sleeps six, offering free Wi-Fi, a Smart TV, a fully equipped kitchen with appliances including a coffee maker, and on-site parking.
Best Middletown, CT vacation rentals with parking
9.0 1 review
Middletown, CT
07/13 – 08/10
$240/nighttotal: $6720 (28 )
Apartment In Middletown-wesleyan 301
1 3
apartment , Middletown
This Middletown apartment offers exceptional proximity to Wesleyan University, just a 6-minute walk away, with Central Connecticut State University 13 miles and Trinity College 14 miles distant. This 950-square-foot unit accommodates up to 6 guests and includes complimentary on-site parking, free Wi-Fi, a fully equipped kitchen with a dishwasher and microwave, and an in-unit washing machine.
Middletown, CT
07/13 – 08/10
$460/nighttotal: $12880 (28 )
Historic Home 3 Mi To Middletown Main Street
6 2
house , Middletown
This historic house in Middletown is located 3 miles from Main Street, 2.1 miles from Wesleyan University, and within 14-19 miles of the Goodspeed Opera House and Wadsworth Atheneum. This 5870 square foot residence offers 6 bedrooms, 3 bathrooms, internet, air conditioning, parking, and a fully equipped kitchen, with a guest capacity of 23.
10 2 reviews
Middletown, CT
07/13 – 08/10
$272/nighttotal: $7616 (28 )
2br Apartment Near Wesleyan 301
2 2
apartment , Middletown
This Washington Street Historic District apartment in Middletown offers on-site parking and is located 0.75 miles from Harbor Park and 0.38 miles from Kidcity Children's Museum. This 950 sq ft dwelling accommodates up to 4 guests with 2 bedrooms, 1 bathroom, and features air conditioning, Wi-Fi, a full kitchen, and an in-unit washer and dryer.
Middletown, CT
07/08 – 07/09
$451/nightfor 1 night
3 Br Apartment Near Wesleyan 201
3 4
apartment , Middletown
This 3-bedroom, 1-bathroom condo is located in Middletown's Washington Street Historic District, a 9-minute walk from Kidcity Children's Museum and a 12-minute walk from Van Vleck Observatory. This 950 sq ft rental sleeps 6 guests and offers on-site parking, Wi-Fi, a full kitchen, and an in-unit washer/dryer, with proximity to Artfarm, Dinosaur State Park, and Cromwell Meadows Wildlife Management Area.
Frequently Asked Questions about vacation rentals in Middletown, CT
Which neighborhood in Middletown, CT should you consider for a vacation rental?
The area around the Wesleyan University campus is a good choice, as it's close to downtown and has a lot of restaurants and shops. If you're looking for something quieter, the neighborhoods around Harbor Park and the Connecticut River are nice options.
What are the best Airbnb and vacation rentals in Middletown, CT?
When is the best time to book a vacation rental in Middletown, CT?
It depends on what you're looking for! If you want to avoid the crowds, the shoulder seasons of spring and fall are great. Summer is the busiest time, but also when there are the most festivals and events. And if you're looking for a winter getaway, Middletown has a charming holiday atmosphere.
What are the most popular Airbnbs in Middletown, CT?
What are the best budget-friendly activities in Middletown, CT?
The Mattabesett Trail is a great place to hike or bike for free, and the Middletown Public Library has a ton of free programs and events. You can also walk or bike along the Connecticut River for some beautiful views.
What are the best vacation rentals with a pool in Middletown, CT?
What are the best restaurants with local dishes in Middletown, CT?
The Black Sheep is a popular spot for local fare, and they have a great selection of craft beers. For something a little more upscale, try the restaurant at the Wadsworth Mansion, which features seasonal menus with local ingredients. And if you're looking for a casual bite, the Main Street Cafe is a great option.
What are the best rentals for families and kids in Middletown, CT?
What are the best walking or cycling routes in Middletown, CT?
The Mattabesett Trail is a great option for both walking and cycling, and it runs for miles along the Connecticut River. You can also walk or bike around the Wesleyan University campus, which has beautiful grounds and a lot of interesting architecture.
What are the best rentals or Airbnbs with a jacuzzi in Middletown, CT?
Are there pet-friendly attractions in Middletown, CT?
Yes, the Mattabesett Trail is a great place to walk your dog, and there are a number of dog-friendly restaurants and cafes in downtown Middletown. The Connecticut River Museum also welcomes leashed dogs on their grounds.
What are the benefits of choosing a vacation rental in Middletown, CT?
Vacation rentals offer more space and privacy than hotels, and they can be a great option for families or groups. They also often come with amenities like kitchens and laundry facilities, which can save you money on meals and laundry.
What are the top sports attractions and facilities in Middletown, CT?
Middletown has a number of sports facilities, including the Wesleyan University athletic complex, which has a track, tennis courts, and a baseball field. The city also has a number of parks with basketball courts, playgrounds, and other recreational facilities.
Destinations nearby
Best Vacation Rentals with Balconies in Middletown, CT
Wake up to breathtaking views at these Middletown, CT vacation rentals with balconies, perfect for your morning coffee.
8.2 10 reviews
Middletown, CT
07/08 – 07/09
$351/nightfor 1 night
Fashionably Cozy Place
2 4
apartment , Meriden
This apartment is situated in Meriden, within easy reach of Wesleyan University (10 miles) and Lake Compounce (14 miles). It has excellent user and location ratings. This 1300 square feet, 2-bedroom, 1-bathroom apartment can accommodate up to 6 guests and features air conditioning, free Wi-Fi, a flat-screen TV, and a fully equipped kitchen. It also offers free on-site parking and allows pets for an additional fee.
10 2 reviews
Middletown, CT
06/27 – 07/04
$495/nighttotal: $3465 (7 )
Cabin Deck House - Formidable Cabin In Laurel Island
4 2
cabin , East Hampton
This charming cabin is located in Laurel Island, just a short drive from East Hampton and its beaches, as well as Wesleyan University and Goodspeed Opera House. The cabin consistently receives excellent reviews for its cleanliness, location, and overall experience. The cabin offers four bedrooms, making it perfect for families or groups of friends. Enjoy the private terrace, garden, and lake views, or prepare meals in the fully equipped kitchen with a fridge and freezer.
8.8 3 reviews
Middletown, CT
07/13 – 08/10
$275/nighttotal: $7700 (28 )
#28- *Modern Bungalow*
2 3
apartment , New Britain
This New Britain vacation rental is conveniently located near Central Connecticut State University, less than 0.3 miles away, providing easy access to Iwo Jima Survivors Memorial Park and the New Britain Museum of American Art within a 3-mile radius. This 950-square-foot house features two bedrooms, one bathroom, and can comfortably accommodate five guests, boasting amenities such as a fully equipped kitchen, in-unit laundry, a balcony, and parking.
9.0 7 reviews
Middletown, CT
07/13 – 08/10
$256/nighttotal: $7168 (28 )
Private Apartment In Berlin
2 3
apartment , Berlin
This Berlin, Maryland vacation home is conveniently located 1.8 miles from New Britain Stadium and 2.5 miles from Putter's Paradise Mini Golf, a 13-minute walk from Berlin Station. This 1190-square-foot house sleeps four, offering two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, in-house laundry, free WiFi, a Smart TV, air conditioning, parking, and a children's playground.
Neighborhoods and points of interest in Middletown, CT
Our Favorite Pet-Friendly Vacation Rentals in Middletown, CT
Experience a pet-friendly stay in Middletown, CT with vacation rentals located steps away from city dog parks and walking trails.
Middletown, CT
07/08 – 07/09
$344/nightfor 1 night
3 Br Apartment Near Wesleyan 201
1 4
apartment , Middletown
This 3-bedroom apartment in Middletown is an 8-minute walk from Wesleyan University and 28 miles from Tweed-New Haven Airport. This 950 square foot dwelling accommodates up to 8 guests with a full kitchen, air conditioning, free Wi-Fi, and on-site parking.
Middletown, CT
07/13 – 08/10
$232/nighttotal: $6496 (28 )
Apartment In Middletown-wesleyan102
1 2
apartment , Middletown
This Middletown rental unit offers a prime location, situated a 7-minute walk from Wesleyan University and within a 14-mile radius of Central Connecticut State University and Trinity College. This 950 square foot residence accommodates up to 5 guests with two bedrooms, a full kitchen, complimentary Wi-Fi, on-site parking, and an in-unit washer.
9.5 103 reviews
Middletown, CT
07/08 – 07/09
$272/nightfor 1 night
59 Old Maids Lane Pool House
1 4
house , Glastonbury
This tiny house is situated in a quiet residential neighborhood near the Connecticut River, hiking trails, and a children's playground. It has excellent user, location, and cleanliness ratings. The house has 1 bedroom and can accommodate up to 4 guests. It features a kitchenette with a microwave, induction burners, pans, and a refrigerator, as well as a shared bathroom with a shower and toilet. Guests can enjoy the shared saltwater pool, stone patio, and pergola, as well as the nearby hiking trails and river.
8.2 9 reviews
Middletown, CT
07/13 – 08/10
$210/nighttotal: $5880 (28 )
2br Apartment Near Wesleyan 102
1 3
apartment , Middletown
This 2-bedroom, 1-bathroom apartment is located in Middletown, a short 300-foot walk from Wesleyan University. This pet-friendly dwelling offers a fully equipped kitchen with a fridge and microwave, air conditioning, parking, and on-site laundry, accommodating up to 4 guests for short or extended stays.
