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Best Vacation rentals and Airbnb offers in Cromwell, CT
8.3 6 reviews
Cromwell, CT
07/02 – 07/05
$295/nighttotal: $885 (3 )
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.
10 169 reviews
Cromwell, CT
09/18 – 09/20
$180/nighttotal: $360 (2 )
Rustic Farmhouse By The River (Duplex)
1 1
gîte , Glastonbury
This South Glastonbury rental, a historic duplex apartment, is conveniently located within walking distance of the Connecticut River and South Glastonbury's shops and restaurants. The one-bedroom, one-bathroom apartment sleeps two guests and features a fully equipped kitchen with dishwasher, in-unit laundry, a smart TV, central air conditioning, and keypad entry; nearby hosts are available for assistance.
Cromwell, CT
07/02 – 07/05
$653/nighttotal: $1959 (3 )
Historic Home 3 Mi To Middletown Main Street
6 3
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.
9.3 52 reviews
Cromwell, CT
07/02 – 07/05
$266/nighttotal: $798 (3 )
The Bee Hive
1 3
apartment , Glastonbury
This Glastonbury home is located just a short distance from the town center and the famous Glastonbury Tor, offering easy access to the area's attractions. Guests consistently praise the property's excellent location, cleanliness, and overall experience. The 3-bedroom home comfortably accommodates up to 6 guests. Enjoy modern amenities like air conditioning, a fully equipped kitchen, high-speed Wi-Fi, and a spacious garden with parking for multiple vehicles.
9.7 135 reviews
Cromwell, CT
09/18 – 09/20
$191/nighttotal: $382 (2 )
Perfect Private "Downtown Village" Apartment
1 1
apartment , Middletown
This studio apartment is located in a historic district of Middletown, just one block from Wesleyan University and the main street with restaurants and coffee shops. The studio has received excellent ratings for its location, cleanliness, and overall experience. This charming apartment can comfortably accommodate two guests and features a fully equipped kitchen, a private bathroom, and a washer and dryer for added convenience. Enjoy the peaceful retreat of the fenced-in rear yard, and take advantage of amenities like a TV, wireless internet, and a private parking space.
9.9 55 reviews
Cromwell, CT
09/18 – 09/20
$854/nighttotal: $1708 (2 )
Hot Tub And Pool Home Away From Home
1 1
apartment , Middletown
This apartment is located in a quiet residential area of Middletown, just a short drive from the bustling downtown and its many restaurants and shops. Guests have consistently rated this rental as excellent in terms of location, cleanliness, and overall experience. The three-bedroom, three-bathroom home comfortably sleeps six guests. Enjoy a relaxing stay with a private backyard featuring a pool, barbecue area, and hot tub, along with a fitness center, a garden, and parking.
10 31 reviews
Cromwell, CT
09/18 – 09/20
$243/nighttotal: $486 (2 )
Cozy Comforts! Country Living At Its Finest - Just 10 Min To Downtown Middletown
1 1
apartment , Haddam
This Higganum apartment rental is located within three miles of Higganum Reservoir, Millers Pond, and the Connecticut Valley Railroad State Park Trail, offering easy access to outdoor recreation. The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen with a refrigerator and washer, a private patio, free WiFi, a Smart TV, a fireplace, and access to shared barbecue grills and a garden.
9.6 5 reviews
Cromwell, CT
09/18 – 09/20
$343/nighttotal: $686 (2 )
“3br Home Near Wesleyan & Downtown Middletown
1 1
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.
10 7 reviews
Cromwell, CT
09/18 – 09/20
$531/nighttotal: $1062 (2 )
Former Train Depot On The River.
1 1
apartment , Rocky Hill
This luxurious three-bedroom, two-bathroom apartment in Rocky Hill, Connecticut, is a short walk from the town center and its restaurants, boasting stunning Connecticut River views, including the historic Rocky Hill Ferry. This former train station conversion, newly built in 2025, offers 6-guest capacity, two outdoor decks, private parking, in-unit laundry, and modern heating/AC.
Cromwell, CT
07/02 – 07/05
$293/nighttotal: $879 (3 )
3 Br Apartment Near Wesleyan 201
1 3
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.
10 3 reviews
Cromwell, CT
07/02 – 07/05
$406/nighttotal: $1218 (3 )
3 Br Apartment Near Wesleyan 202
1 3
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.
10 25 reviews
Cromwell, CT
07/02 – 07/05
$459/nighttotal: $1377 (3 )
John Hollister Home On The Farm
1 3
gîte , Glastonbury
This historic Glastonbury, Connecticut farmhouse rental, Killam & Bassette Farmstead, built in 1675, sits on a working farm a short walk from the Connecticut River. This three-bedroom, two-bathroom vacation home sleeps twelve guests and features a fully equipped kitchen with dishwasher, air conditioning, parking, and internet access, offering scenic farm walks and proximity to Glastonbury's town center.
Top Vacation Rentals for Families in Cromwell, CT
These family-friendly vacation rentals in Cromwell, CT offer spacious layouts and easy access to top city attractions.
9.8 14 reviews
Cromwell, CT
09/18 – 09/20
$757/nighttotal: $1514 (2 )
Walk To Lake: Middlefield Home W/ Fire Pit
4 1
apartment , Middlefield
This family-friendly vacation home in Middlefield is located just a short distance from Lake Beseck Beach, Indian Springs Golf Club, Lyman Orchards, and Powder Ridge Mountain Park and Resort, making it a great base for exploring the area. Travelers have rated this property excellent, making it a popular choice for families and groups. This 2,500 square foot house has four bedrooms, three bathrooms, and can comfortably accommodate up to eight guests. The home is equipped with a fully equipped kitchen, a fireplace, a game room, a terrace, a garden, a spa, and parking, making it ideal for a relaxing and enjoyable vacation.
9.9 74 reviews
Cromwell, CT
09/18 – 09/20
$136/nighttotal: $272 (2 )
Cozy, Spacious, Central Getaway
1 1
apartment , Berlin
This house in Berlin is centrally located, offering easy access to the city's attractions and amenities. It has received excellent ratings for location, cleanliness, and user experience. The home features a private patio and fenced yard, perfect for relaxing outdoors. Guests can enjoy a comfortable queen-size bed, a fully equipped kitchen, and a dedicated workspace with reliable Wi-Fi.
9.8 338 reviews
Cromwell, CT
07/02 – 07/05
$270/nighttotal: $810 (3 )
Historic Greek Revival Brick Home
1 3
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.
9.8 14 reviews
Cromwell, CT
09/18 – 09/20
$811/nighttotal: $1622 (2 )
Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University
3 1
apartment , Middletown
This Middletown mountainside vacation home boasts a prime location, just within 3 miles of Smith Park and Falcon Field, and 6 miles from Kidcity Children's Museum and Wadsworth Falls State Park. This 3,500-square-foot house comfortably sleeps six guests in three bedrooms and four bathrooms, featuring a fully equipped kitchen, swimming pool, jacuzzi, fitness center, and free Wi-Fi—all within a family-friendly setting.
Best Cromwell, CT vacation rentals with parking
Cromwell, CT
09/18 – 09/20
$378/nighttotal: $756 (2 )
Charming Connecticut Hideaway: Year-round Fun!
2 1
apartment , Middlefield
This Middlefield vacation rental is a secluded single-story home offering easy access to Wadsworth Falls State Park (2 miles), Powder Ridge Mountain Park (3 miles), and Wesleyan University (4 miles). This 1180 sq ft apartment accommodates up to 6 guests and features a dedicated WFH area, a well-equipped kitchen with stainless steel appliances, a furnished deck with a gas grill, and a spacious yard with accessible entry.
9.7 43 reviews
Cromwell, CT
09/18 – 09/20
$730/nighttotal: $1460 (2 )
Walk To Lake: Middlefield Home W/ Fire Pit
4 1
house , Middlefield
This 4-bedroom vacation rental is located in Middlefield, Connecticut, just 6.6 miles from Wesleyan University and 17 miles from Central Connecticut State University. Guests have consistently rated the home excellent for its location, cleanliness, and overall experience. The 2,500 square foot house comfortably sleeps 8 guests. The home features a fully equipped kitchen, a game room, a spa, a garden, and free Wi-Fi, providing everything you need for a relaxing and enjoyable stay.
9.4 6 reviews
Cromwell, CT
07/02 – 07/05
$687/nighttotal: $2061 (3 )
#29 - Modern 5 Bedroom/2 Bath
5 3
apartment , Middletown
This stylish 5-bedroom apartment is located in a private neighborhood in Middletown, Connecticut, minutes away from Wadsworth Falls State Park, Dinosaur State Park, and Wesleyan University. It has an excellent user rating. The apartment offers a spacious layout with 1700 square feet of floor area and can accommodate up to 10 guests. It features modern amenities such as herringbone flooring, high-speed internet, smart TVs, a fully equipped kitchen, comfortable bedding, and entertainment options. Guests staying 3+ months have exclusive garage access.
9.9 21 reviews
Cromwell, CT
07/02 – 07/05
$172/nighttotal: $516 (3 )
Modern 1br Near Wesleyan & Main Street
1 3
apartment , Middletown
This Middletown apartment rental is conveniently located near Main Street, a mile from Wesleyan University, and close to Middlesex Hospital, offering easy access to Route 9. The newly renovated one-bedroom unit sleeps three guests and features a full kitchen with dishwasher, in-unit laundry, air conditioning, and off-street parking.
Frequently Asked Questions about vacation rentals in Cromwell, CT
What should a first-time visitor not miss in Cromwell, CT?
You should definitely check out the Cromwell Historical Society Museum to learn about the town's history. And for some outdoor fun, head to the Cromwell Town Park for a picnic or a walk.
What are the best Airbnb and vacation rentals in Cromwell, CT?
Which neighborhood in Cromwell, CT should you consider for a vacation rental?
The area around the Cromwell Town Park and the Middlesex Canal is a great place to find a vacation rental. It's close to the action but still has a quiet, residential feel.
What are the most popular Airbnbs in Cromwell, CT?
What are the top family-friendly attractions in Cromwell, CT?
The Cromwell Town Park is a great spot for families with its playground, picnic areas, and walking trails. The Cromwell Historical Society Museum is also fun for kids, with exhibits on local history.
What are the best vacation rentals with a pool in Cromwell, CT?
The best vacation rental with a pool in Cromwell, CT is Solace Living.
When is the best time to book a vacation rental in Cromwell, CT?
The best time to book a vacation rental in Cromwell is during the shoulder seasons, spring and fall, when the weather is still pleasant but the crowds are smaller.
What are the best budget-friendly activities in Cromwell, CT?
Take a walk or bike ride along the Middlesex Canal Towpath. It's a beautiful and scenic way to spend an afternoon. You can also visit the Cromwell Town Park for a picnic or to play some games.
What are the best restaurants with local dishes in Cromwell, CT?
The Cromwell Diner is a local favorite, serving classic American comfort food. For a more upscale dining experience, try The Restaurant at the Cromwell Country Club.
What are the best walking or cycling routes in Cromwell, CT?
The Middlesex Canal Towpath is a great option for both walking and cycling. It's a paved path that follows the historic canal, offering scenic views of the Connecticut River.
Are there pet-friendly attractions in Cromwell, CT?
The Cromwell Town Park is a great spot to bring your furry friend. There are plenty of walking trails and open spaces for them to enjoy.
What are the benefits of choosing a vacation rental in Cromwell, CT?
Vacation rentals offer more space and privacy than hotels, often at a lower price. They also provide a more home-like experience, with access to a kitchen and laundry facilities.
What are the top sports attractions and facilities in Cromwell, CT?
Cromwell doesn't have any major sports teams or stadiums, but there are plenty of places to play sports, like the Cromwell Town Park, which has baseball fields, basketball courts, and tennis courts.
Destinations nearby
Best Vacation Rentals with Balconies in Cromwell, CT
Start your morning right with a vacation rental in Cromwell, CT featuring a private balcony and stunning views.
Cromwell, CT
09/18 – 09/20
$429/nighttotal: $858 (2 )
3 Br Apartment Near Wesleyan 201
3 1
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.
Cromwell, CT
09/18 – 09/20
$504/nighttotal: $1008 (2 )
3 Br Apartment Near Wesleyan 202
3 1
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.
Our Favorite Pet-Friendly Vacation Rentals in Cromwell, CT
Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Cromwell, CT are steps away from dog parks and city walks.
9.5 103 reviews
Cromwell, CT
09/18 – 09/20
$179/nighttotal: $358 (2 )
59 Old Maids Lane Pool House
1 1
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.
Cromwell, CT
09/18 – 09/20
$351/nighttotal: $702 (2 )
2br Apartment Near Wesleyan 102
2 1
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.
Cromwell, CT
09/18 – 09/20
$269/nighttotal: $538 (2 )
Apartment In Middletown-wesleyan102
1 1
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.
10 2 reviews
Cromwell, CT
07/02 – 07/05
$365/nighttotal: $1095 (3 )
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.