Best Holiday rentals and Airbnb offers in Middletown, CT
Middletown, CT
30/06 – 02/07
SG$320/nighttotal: SG$640 (2 )
3 Br Apartment Near Wesleyan 201
1 2
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.
9.8 15 reviews
Middletown, CT
30/06 – 02/07
SG$945/nighttotal: SG$1890 (2 )
Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University
3 2
apartment , Middletown
This Middletown holiday home boasts a mountainside location, within 5km of Smith Park and Falcon Field, and 10km of Kidcity Children's Museum and Wadsworth Falls State Park. The 325 square metre property sleeps six guests across three bedrooms and four bathrooms, offering a swimming pool, jacuzzi, fitness centre, and free Wi-Fi alongside a fully equipped kitchen.
10 1 review
Middletown, CT
30/06 – 02/07
SG$411/nighttotal: SG$822 (2 )
3 Br Apartment Near Wesleyan 201
1 2
apartment , Middletown
This spacious second-floor flat is located in Middletown, a mere 300 meters from Wesleyan University. This pet-friendly accommodation offers three bedrooms, sleeping up to six guests, and features a fully equipped kitchen, on-site laundry facilities, and a porch area for outdoor relaxation.
8.7 95 reviews
Middletown, CT
13/07 – 10/08
SG$307/nighttotal: SG$8596 (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.
9.8 338 reviews
Middletown, CT
30/06 – 02/07
SG$275/nighttotal: SG$550 (2 )
Historic Greek Revival Brick Home
2 2
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.
9.9 22 reviews
Middletown, CT
30/06 – 02/07
SG$302/nighttotal: SG$604 (2 )
Modern 1br Near Wesleyan & Main Street
1 2
apartment , Middletown
This Middletown flat is conveniently located near Main Street's shops and restaurants, a 1.6km stroll from Wesleyan University, and close to Middlesex Hospital, with easy access to Route 9. The newly renovated ground-floor apartment sleeps three, features a full kitchen with dishwasher, in-unit laundry, off-street parking, and air conditioning; enjoy nearby attractions and the comfort of this well-equipped dwelling.
Middletown, CT
13/07 – 10/08
SG$722/nighttotal: SG$20216 (28 )
Serene 3-bedroom House With Ac In Charming Berlin
3 3
apartment , Berlin
This Berlin flat offers a local experience, situated a short distance from the Barnes Museum and Iwo Jima Survivors Memorial Park. This 3-bedroom, 3-bathroom apartment accommodates up to 6 guests and is equipped with internet, air conditioning, heating, an iron, and a hairdryer, with family-friendly attractions and entertainment venues nearby.
Middletown, CT
13/07 – 10/08
SG$1271/nighttotal: SG$35588 (28 )
Conference Room Rental No Sleeping Arrangements
1 3
apartment , Cromwell
This Cromwell apartment is situated less than 1.6km from the Connecticut River and its State Wildlife Area, and within 4.8km of River Highlands State Park and the TPC River Highlands golf course. The one-bedroom flat offers a sofa bed, sleeping up to 30 guests, free Wi-Fi, air conditioning, and is close to hiking trails and scenic river walks.
9.8 15 reviews
Middletown, CT
30/06 – 02/07
SG$974/nighttotal: SG$1948 (2 )
Walk To Lake: Middlefield Home W/ Fire Pit
4 2
apartment , Middlefield
This family-friendly holiday home is located in Middlefield, just 3 kilometres from Lake Beseck Beach and Indian Springs Golf Club, with Lyman Orchards and Powder Ridge Mountain Park and Resort within 5 kilometres. It has excellent user ratings and is perfect for a family holiday. The property has 4 bedrooms and 3 bathrooms across 232 square metres, comfortably accommodating up to 8 guests. It features a fully equipped kitchen, a terrace, a garden, a spa, air conditioning, parking, and internet access, ensuring a comfortable and enjoyable stay.
9.4 20 reviews
Middletown, CT
13/07 – 10/08
SG$187/nighttotal: SG$5236 (28 )
Stylish And Cozy 2
1 3
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.
8.0 61 reviews
Middletown, CT
13/07 – 10/08
SG$234/nighttotal: SG$6552 (28 )
Two Families, Up And Down Stairs, The 2nd Floor Is The Vrbos Apartment
3 3
apartment , New Britain
This New Britain apartment is situated in a peaceful and safe neighbourhood, just a short distance from Central Connecticut State University (CCSU) and local amenities. The apartment has received very good ratings for location, cleanliness and overall user experience. The property has three bedrooms and a bathroom, along with a living area, full kitchen and dining room. It includes amenities such as air conditioning, parking, internet and a microwave.
8.8 3 reviews
Middletown, CT
13/07 – 10/08
SG$349/nighttotal: SG$9772 (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.
Best family friendly Middletown, CT holiday rentals
Among the 100 accommodations in Middletown, CT, here are the 4 best family friendly rentals
10 313 reviews
Middletown, CT
30/06 – 02/07
SG$264/nighttotal: SG$528 (2 )
Guesthouse Farm Stay
1 2
house , Portland
This studio apartment is situated on a 12-acre working farm in Portland, Connecticut, just a short drive from Middletown, Glastonbury, and Wesleyan University. The self-catering studio, housed in a beautifully restored 1800s barn, offers a unique blend of modern comfort and historic charm, with an open plan layout accommodating up to four guests and featuring a private back deck overlooking pastures.
9.7 257 reviews
Middletown, CT
30/06 – 02/07
SG$285/nighttotal: SG$570 (2 )
Beautiful Sunny Apartment In Historic Village
1 2
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.
9.9 95 reviews
Middletown, CT
30/06 – 02/07
SG$333/nighttotal: SG$666 (2 )
Updated 2-bedroom Near Wesleyan-middletown
1 2
apartment , Middletown
This Middletown apartment is conveniently located near Main Street, Wesleyan University, and Middlesex Hospital, offering easy access to Route 9. The newly renovated 2-bedroom flat sleeps four, features a full kitchen with dishwasher, laundry facilities, a private back porch, and self check-in; free on-street parking is also available.
9.6 31 reviews
Middletown, CT
13/07 – 10/08
SG$188/nighttotal: SG$5264 (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.
Best Middletown, CT holiday rentals with parking
Middletown, CT
13/07 – 10/08
SG$383/nighttotal: SG$10724 (28 )
Simple Comfort And Tranquility
1 3
apartment , New Britain
This New Britain flat is a 15-minute walk from the New Britain Museum of American Art and a 7-minute walk from Walnut Hill Park, offering convenient access to city attractions. This apartment features air conditioning, Wi-Fi, a fully equipped kitchen with an oven and fridge, and on-site covered garage parking, with nearby attractions including Winding Trails Recreation and Nature Association and Dinosaur State Park.
9.0 9 reviews
Middletown, CT
30/06 – 02/07
SG$239/nighttotal: SG$478 (2 )
Criscaris Homes
1 2
apartment , New Britain
This New Britain apartment, located 3.7 kilometres from Central Connecticut State University and within a 14.5 kilometre radius of attractions such as the Bushnell Center for the Performing Arts and the Wadsworth Atheneum Museum of Art, offers convenient access to local amenities. This self-catering flat boasts 11 square metres of floor space, sleeps seven guests, and includes a fully equipped kitchen, free Wi-Fi, in-unit laundry, and private parking.
9.0 7 reviews
Middletown, CT
13/07 – 10/08
SG$329/nighttotal: SG$9212 (28 )
Private Apartment In Berlin
2 3
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.
9.7 43 reviews
Middletown, CT
30/06 – 02/07
SG$939/nighttotal: SG$1878 (2 )
Walk To Lake: Middlefield Home W/ Fire Pit
4 2
house , Middlefield
This comfortable house is located in Middlefield, a short drive from Wesleyan University and Central Connecticut State University, offering a peaceful setting away from the hustle and bustle of city life. The property has consistently received excellent ratings for its cleanliness, location, and overall experience. This four-bedroom house spans 232 square metres and comfortably accommodates up to eight guests. The property boasts modern amenities, including a fully equipped kitchen, a spacious living area, and a game room for entertainment, making it ideal for families or groups of friends.
Frequently asked questions about holiday rentals in Middletown, CT
What are the top family-friendly attractions in Middletown, CT?
The Connecticut Valley Railroad is always a hit with families, and the kiddos will love the interactive exhibits at the Connecticut Science Center. If it's a nice day, head to the Rockfall State Park for some outdoor fun.
What are the best Airbnb and vacation rentals in Middletown, CT?
When is the best time to book a vacation rental in Middletown, CT?
You'll want to book your vacation rental in advance, especially if you're planning to visit during peak season, which is from June to August. If you're looking for a quieter trip, consider visiting during the shoulder seasons, in the spring or autumn.
What are the most popular Airbnbs in Middletown, CT?
What events or festivals should visitors check out in and around Middletown, CT?
The annual Middletown Arts Festival is a great event to catch, and there are also plenty of smaller festivals and events throughout the year. Check the Middletown website for a full list of events.
What are the best vacation rentals with a pool in Middletown, CT?
What are the best budget-friendly activities in Middletown, CT?
Take a walk along the Connecticut River, explore the gardens at the Wadsworth Mansion, or visit the Russell Library for free. You can also find some great deals on food and drinks at the local restaurants.
What are the best rentals for families and kids in Middletown, CT?
What are the best restaurants with local dishes in Middletown, CT?
The Main Street Cafe is a great spot for classic American comfort food. For something a little more upscale, try the A Mano, which serves modern Italian cuisine. And for something a bit more casual, head to the Little Grill on the Avenue for some delicious burgers and fries.
What are the best rentals or Airbnbs with a jacuzzi in Middletown, CT?
What are the best walking or cycling routes in Middletown, CT?
The Mattabesett Trail is a great option for a scenic walk or bike ride. You can also explore the historic downtown area, which is full of charming shops and restaurants.
Are there pet-friendly attractions in Middletown, CT?
Many of the parks in Middletown are dog-friendly, including the Rockfall State Park. You can also find some pet-friendly restaurants and shops in the downtown area.
What are the benefits of choosing a vacation rental in Middletown, CT?
Vacation rentals offer more space and privacy than a hotel room. They're also a great option for families or groups of friends travelling together. You can often find vacation rentals with kitchens, which allows you to save money on dining out.
What are the top sports attractions and facilities in Middletown, CT?
Middletown is home to the Wesleyan University athletic facilities, which include a football stadium, a baseball field, and a tennis complex. There are also several public parks with sports fields and courts.
Destinations nearby
Best Middletown, CT holiday rentals with a balcony
Middletown, CT
30/06 – 02/07
SG$497/nighttotal: SG$994 (2 )
3 Br Apartment Near Wesleyan 202
3 2
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.
10 2 reviews
Middletown, CT
27/06 – 04/07
SG$637/nighttotal: SG$4459 (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.
9.8 23 reviews
Middletown, CT
30/06 – 02/07
SG$446/nighttotal: SG$892 (2 )
#24 *Serenity* A Lakefront Cottage Retreat
2 2
apartment , Middletown
This Middletown lakefront property, a 102-square-metre cottage, is situated a 10-minute (approx. 6.4km) drive from Middletown's city centre, offering easy access to Wesleyan University and Harbor Park. The self-catering holiday home sleeps four, boasting two queen-size beds (one hybrid pillow top, one memory foam), a 55-inch smart TV, a KitchenAid-equipped kitchen, and a modern bathroom with heated fan and backlit anti-fog mirror; pets (non-shedding hypoallergenic dogs only) are welcome.
Middletown, CT
30/06 – 02/07
SG$430/nighttotal: SG$860 (2 )
3 Br Apartment Near Wesleyan 201
3 2
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.
Best pet friendly Middletown, CT holiday rentals
Among the 100 accommodations in Middletown, CT, here are the 4 best pet friendly rentals
8.0 7 reviews
Middletown, CT
13/07 – 10/08
SG$265/nighttotal: SG$7420 (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.
8.0 1 review
Middletown, CT
13/07 – 10/08
SG$359/nighttotal: SG$10052 (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.
10 51 reviews
Middletown, CT
30/06 – 02/07
SG$985/nighttotal: SG$1970 (2 )
Ct River Retreat - Modern Home With Ct River Views
1 2
apartment , East Hampton
This three-bedroom house is located in East Hampton, just 160 metres from Saint Clements Castle & Marina and 11 kilometres from Wesleyan University, offering a peaceful retreat near local attractions. The property features a spacious open-plan layout, perfect for groups of up to six guests. Amenities include a well-equipped kitchen, private decks with river views, a wrap-around balcony, a double-sided fireplace, high-speed Wi-Fi, and a smart TV.
9.4 95 reviews
Middletown, CT
30/06 – 02/07
SG$378/nighttotal: SG$756 (2 )
#24 *Serenity* A Lakefront Cottage Retreat
2 2
apartment , Middletown
This two-bedroom lakefront apartment is located near Middletown, just a short distance from the town centre, Rocky Hill and popular restaurants. The apartment offers a comfortable stay for up to four guests, boasting a modern kitchen, a spacious back deck with lake views and a dedicated workspace.