Compare Vacation Rentals & Airbnb in Middletown, CT

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Middletown, CT vacation rentals
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159 Rentals and Airbnb in Middletown, CT

Best family friendly Middletown, CT vacation rentals

Among the 159 accommodations in Middletown, CT, here are the 4 best family friendly rentals

Hot Tub And Pool Home Away From Home - Middletown, CT
9.9 55 reviews

Hot Tub And Pool Home Away From Home

apartment, Middletown
This apartment is situated in a quiet, family-friendly neighbourhood in Middletown, just a short drive from the town centre and a few blocks from the peaceful Middletown Park. The property has received excellent ratings for its location, cleanliness, and overall experience.
The three-bedroom apartment comfortably accommodates up to six guests. The property offers a range of amenities, including a private backyard with a swimming pool, hot tub, and barbecue area, a fully equipped kitchen, and a fitness centre.
A Luxury Estate Historic Spacious~white Lion Manor - Middletown, CT
10 95 reviews

A Luxury Estate Historic Spacious~white Lion Manor

apartment, Middletown
This spacious house is located in Middletown, Connecticut, a short distance from Wesleyan University and within a 2-mile radius of the town centre, offering easy access to shops, restaurants, and supermarkets. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has 9 bedrooms and 8 bathrooms, comfortably accommodating up to 16 guests. With a private pool, hot tub, sauna, theatre room, and a large patio, there are plenty of opportunities for relaxation and entertainment.
Amazing Lakefront Property - Middletown, CT
9.4 30 reviews

Amazing Lakefront Property

apartment, Middlefield
This waterfront property is located just 2 kilometres from Lake Beseck Beach, Powder Ridge Mountain Park and Resort, and Lyman Orchards, offering easy access to a range of attractions and outdoor activities. It has received excellent user ratings, making it a popular choice for travellers.
The house offers 4 bedrooms and 4 bathrooms across a spacious 316 square metres, comfortably accommodating up to 10 guests. Enjoy the garden, barbecue grills, and balcony, along with modern amenities like free WiFi, a fireplace, and a fully equipped kitchen.
Spacious And Quiet - Middletown, CT
8.0 7 reviews

Spacious And Quiet

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.

Best Middletown, CT vacation rentals with parking

3 Br Apartment Near Wesleyan 201 - Middletown, CT
8.6 7 reviews

3 Br Apartment Near Wesleyan 201

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.
Criscaris Homes - Middletown, CT
8.9 9 reviews

Criscaris Homes

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.
#24 *Serenity* A Lakefront Cottage Retreat - Middletown, CT
9.4 95 reviews

#24 *Serenity* A Lakefront Cottage Retreat

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.
3 Br Apartment Near Wesleyan 202 - Middletown, CT
9.6 5 reviews

3 Br Apartment Near Wesleyan 202

apartment, Middletown
This three-bedroom flat in Middletown offers a prime location, just a short distance from Wesleyan University, making it ideal for visitors to the area.
With capacity for six guests, this pet-friendly accommodation includes a fully equipped kitchen, air conditioning, and a garden, suitable for both short and extended stays.

Frequently Asked Questions about vacation rentals in Middletown, CT

  • What are the top family-friendly attractions in Middletown, CT?

    Middletown has a few family-friendly attractions, like the Connecticut River Museum with its interactive exhibits and the Russell Library, which has a great children's section.
  • What are the best Airbnb and vacation rentals in Middletown, CT?

    Quaint 2br Apt- 1 Block Walk To Wesleyan & Main St, 3 Bedroom Near Wesleyan - Downtown and Apartment Near Wesleyan - Downtown - Wedding Venues are the most popular Airbnb and vacation rentals in Middletown, CT among travelers.

  • When is the best time to book a vacation rental in Middletown, CT?

    You'll want to book in advance for the summer months, especially if you're planning to be there during the festivals. September and October are also busy due to the autumn foliage.
  • What are the most popular Airbnbs in Middletown, CT?

  • What events or festivals should visitors check out in and around Middletown, CT?

    Middletown has a few events throughout the year, like the annual Middletown Arts Festival in June and the Riverfront Concert Series in the summer. Just outside of Middletown, you can check out the annual Apple Harvest Festival in nearby Glastonbury.
  • What are the best vacation rentals with a pool in Middletown, CT?

  • What are the best budget-friendly activities in Middletown, CT?

    Take a stroll along the scenic Connecticut River Trail, it's free and offers beautiful views. The Russell Library is a great place to spend a few hours browsing, and they have free events throughout the year.
  • What are the best rentals for families and kids in Middletown, CT?

  • What are the best restaurants with local dishes in Middletown, CT?

    Try the lobster bisque at The Black Sheep, it's a local favourite. The Main Street Cafe is a good spot for a casual meal, and their clam chowder is excellent.
  • What are the best rentals or Airbnbs with a jacuzzi in Middletown, CT?

    The best vacation rentals or Airbnb with a jacuzzi in Middletown, CT are A Luxury Estate Elegant & Private~white Lion Manor, Lovely 3 Bedroom Colonial Home and Newly Remodeled Entire Apartment & Loft.

  • What are the best walking or cycling routes in Middletown, CT?

    The Connecticut River Trail is a great option for a walk or bike ride. It runs along the river and offers beautiful views. For a shorter walk, try the scenic path around the Wesleyan University campus.
  • Are there pet-friendly attractions in Middletown, CT?

    Many of the parks in Middletown are dog-friendly, like the Harbor Park and the Wickham Park. The Connecticut River Museum also welcomes well-behaved dogs on leashes.
  • What are the benefits of choosing a vacation rental in Middletown, CT?

    Vacation rentals offer more space and privacy than a hotel, and often come with amenities like a kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups.
  • What are the top sports attractions and facilities in Middletown, CT?

    Middletown has a few sports facilities, including the Wesleyan University athletic fields and the Palmer Field, which is home to the local baseball team, the Middletown Blue Dragons.

Popular destinations

Best Middletown, CT vacation rentals with a balcony

Lake Me Home - Middletown, CT
9.0 2 reviews

Lake Me Home

house, East Hampton
Lake Me Home, a beachfront property in East Hampton, offers direct beach access and is situated 18 kilometres from Wesleyan University and the Goodspeed Opera House, and 48 kilometres from Bradley International Airport.
This East Hampton holiday home boasts 684 square metres of floor space, featuring two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, free Wi-Fi, a sun terrace, private parking, and accommodates up to nine guests.
3 Bedrooms Fully Finished - Middletown, CT
9.0 1 review

3 Bedrooms Fully Finished

apartment, Middletown
This Middletown apartment, sleeping up to 11 guests, offers free parking and Wi-Fi.
The self-catering flat features two bedrooms, a fully equipped kitchen, a bathroom, and a balcony, with access to a flat-screen TV.
24 Serenity A Lakefront Cottage Retreat - Middletown, CT
No reviews

24 Serenity A Lakefront Cottage Retreat

house, Middletown
This Middletown lakefront cottage, situated 4.3km from Wesleyan University and within a 19-24km radius of Central Connecticut State University, the Wadsworth Atheneum, and the Bushnell Center for the Performing Arts, offers serene lake views and easy access to local attractions.
The 62 square metre property features one bathroom, accommodates seven guests, and includes a fully equipped kitchen, private balcony, washing machine, air conditioning, Wi-Fi, and pet-friendly access.
#28- *Modern Bungalow* - Middletown, CT
8.8 3 reviews

#28- *Modern Bungalow*

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 pet friendly Middletown, CT vacation rentals

Among the 159 accommodations in Middletown, CT, here are the 4 best pet friendly rentals

Renovated Single Family Home In Central Ct - Middletown, CT
10 9 reviews

Renovated Single Family Home In Central Ct

apartment, Middletown
This Middletown flat is located a short drive from Wesleyan University, major airports, and various dining, shopping, and entertainment venues.
This three-bedroom flat accommodates up to five guests, offering single-floor living, central air conditioning, a well-equipped kitchen with a dishwasher, and a dedicated office space, with parking and a garden available.
Guesthouse Farm Stay - Middletown, CT
10 332 reviews

Guesthouse Farm Stay

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.
Family-friendly Lakeside Cottage With Spectacular Sunset Views Pet-friendly! - Middletown, CT
10 18 reviews

Family-friendly Lakeside Cottage With Spectacular Sunset Views Pet-friendly!

cottage, East Hampton
This lakeside property in the Lake Pocotopaug area of East Hampton, Connecticut, offers easy access to Hurd State Park and George D. Seymour State Park (driving distances vary).
The recently renovated two-bedroom, two-bathroom holiday home sleeps six, boasting a fully equipped kitchen, king-size beds, a living room with a sofa bed, a private patio with barbecue, and on-site laundry facilities; two kayaks and two paddleboards are included for use on the lake.
Rv/camper Farm Stay - Middletown, CT
9.9 87 reviews

Rv/camper Farm Stay

gîte, Portland
This charming gîte is situated in a peaceful rural setting near Portland, Connecticut, just a short drive from Middletown and Glastonbury. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The renovated 1961 Shasta camper comfortably accommodates up to four guests and features a full kitchenette, a bathroom with a shower, and a Keurig coffee maker. Guests can enjoy the tranquility of a working farm, participate in farm chores, and explore the surrounding historical structures.
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