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Best Vacation rentals and Airbnb offers in Middletown, CT
9.3 9 reviews
Middletown, CT
07/13 – 08/10
$111/nighttotal: $3108 (28 )
Quaint Studio Walkable To Downtown And Wesleyan
1 2
apartment , Middletown
This Middletown studio apartment is conveniently located half a mile from Wesleyan University and one mile from downtown Middletown's restaurants and shops. The unit features a double bed, private bathroom with shower, basic kitchen with hot plate, microwave, refrigerator, and electric kettle, and comfortably sleeps two guests.
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.
9.1 29 reviews
Middletown, CT
07/13 – 08/10
$189/nighttotal: $5292 (28 )
Private Apartment In Berlin
1 3
house , Berlin
This charming townhome is located in Berlin, Connecticut, just a short drive from the town center and the Berlin Turnpike. It offers easy access to restaurants, shops, and attractions. This two-bedroom townhome can comfortably accommodate up to five guests. The townhome features a well-equipped kitchen with modern appliances, a spacious backyard, a private driveway, and a peaceful three-season porch. Guests can enjoy the tranquility of the backyard or relax on the porch while enjoying the fresh air.
Middletown, CT
07/08 – 07/09
$435/nightfor 1 night
3 Br Apartment Near Wesleyan 201
1 4
apartment , Middletown
This second-floor apartment in Middletown is located a stone's throw from Wesleyan University, offering convenient access to the campus and surrounding area. This pet-friendly residence accommodates up to six guests with three bedrooms, one bathroom, and a fully equipped kitchen, featuring a porch and on-site laundry for added convenience.
9.8 338 reviews
Middletown, CT
07/08 – 07/09
$341/nightfor 1 night
Historic Greek Revival Brick Home
1 4
apartment , Middletown
This charming apartment is situated in the Downtown Village Historic District, just a block from Main Street, across from the public library, and within walking distance of Wesleyan University. The accommodation has received excellent user, location, and cleanliness ratings, making it a popular choice among travelers. The apartment offers two bedrooms and one bathroom, comfortably accommodating up to six guests. Guests can enjoy a fully equipped kitchen, a private backyard with a patio, a fire pit, and a tire swing, a shared laundry area, and a private entrance with outdoor seating.
8.0 9 reviews
Middletown, CT
07/13 – 08/10
$200/nighttotal: $5600 (28 )
Fashionably Cozy Place
2 3
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.
9.0 7 reviews
Middletown, CT
07/08 – 07/09
$371/nightfor 1 night
Private Apartment In Berlin
2 4
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.
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.
Middletown, CT
07/13 – 08/10
$285/nighttotal: $7980 (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.
Middletown, CT
07/13 – 08/10
$323/nighttotal: $9044 (28 )
3 Br Apartment Near Wesleyan 202
1 3
apartment , Middletown
This 1000 sq ft, 3-bedroom apartment is located near Wesleyan University in Middletown, offering 1 bathroom and accommodating up to 8 guests. This rental includes air conditioning, a full kitchen with a dishwasher and oven, complimentary on-site parking, and free high-speed WiFi.
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.
9.9 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.
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.
9.6 31 reviews
Middletown, CT
07/13 – 08/10
$147/nighttotal: $4116 (28 )
Fashionably Cozy Place
1 3
apartment , Meriden
This Meriden apartment is conveniently located near Hubbard Park, Gouveia Vineyards, and within easy reach of New Haven and Hartford. Guests consistently rate the apartment highly for its cleanliness, location, and overall experience. The apartment is comfortable and spacious, accommodating up to four guests. Amenities include a fully equipped kitchen, high-speed internet, flat-screen TVs in each bedroom, on-site laundry, and parking.
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.
8.0 59 reviews
Middletown, CT
06/27 – 07/04
$214/nighttotal: $1498 (7 )
Two Families, Up And Down Stairs, The 2nd Floor Is The Vrbos Apartment
3 2
apartment , New Britain
This 3-bedroom apartment is located in a quiet neighborhood in New Britain, close to Central Connecticut State University and within easy reach of shopping malls, restaurants, and eateries. It has a very good user rating and location rating, as well as a very good cleanliness rating. The apartment is designed for comfort and offers ample space for up to 6 guests. It features a fully equipped kitchen, a formal dining room, and a comfortable living area, making it ideal for self-catering and family gatherings.
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.
Best Middletown, CT vacation rentals with parking
Middletown, CT
07/13 – 08/10
$244/nighttotal: $6832 (28 )
Apartment In Middletown-wesleyan102
1 3
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.
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.
8.0 7 reviews
Middletown, CT
07/13 – 08/10
$204/nighttotal: $5712 (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.
9.0 1 review
Middletown, CT
07/13 – 08/10
$244/nighttotal: $6832 (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.
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.
8.8 3 reviews
Middletown, CT
07/13 – 08/10
$275/nighttotal: $7700 (28 )
#28- *Modern Bungalow*
2 2
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.
Middletown, CT
07/13 – 08/10
$384/nighttotal: $10752 (28 )
3 Br Apartment Near Wesleyan 202
3 3
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.
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 94 reviews
Middletown, CT
07/13 – 08/10
$237/nighttotal: $6636 (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.
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.
10 2 reviews
Middletown, CT
07/13 – 08/10
$286/nighttotal: $8008 (28 )
2br Apartment Near Wesleyan 301
2 3
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.
10 3 reviews
Middletown, CT
07/13 – 08/10
$283/nighttotal: $7924 (28 )
3 Br Apartment Near Wesleyan 202
1 2
apartment , Middletown
This 3-bedroom, 1-bathroom apartment in Middletown offers a prime location, a short distance from Wesleyan University, ideal for visitors and business travelers. This pet-friendly residence accommodates up to 6 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, and a garden for your convenience.
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.
8.5 11 reviews
Middletown, CT
07/13 – 08/10
$233/nighttotal: $6524 (28 )
Private Apartment In Berlin
1 2
house , Berlin
This townhome is located in Berlin, Connecticut, just 10 miles from Wesleyan University and 11 miles from Bushnell Center for Performing Arts, making it a convenient base for exploring both the city and the surrounding countryside. This property has consistently received excellent ratings for user experience, location, and cleanliness. The two-bedroom home offers 1190 square feet of space, comfortably accommodating up to 9 guests. Enjoy modern conveniences like free Wi-Fi, a fully equipped kitchen, a TV, and comfortable bedding, along with a spa, air conditioning, and free parking.
