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

Historic Greek Revival Brick Home - Middletown, CT
9.8 344 reviews

Historic Greek Revival Brick Home

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.
3 Br Apartment Near Wesleyan 202 - Middletown, CT
9.6 6 reviews

3 Br Apartment Near Wesleyan 202

apartment, Middletown
This spacious flat is located in central Middletown, a short distance from Wesleyan University and within walking distance of local amenities, offering convenient access to restaurants, shops, and parks.
This three-bedroom residence accommodates up to six guests, featuring a fully equipped kitchen with modern appliances, air conditioning, parking, and is pet-friendly, with a porch accessible from the living room for outdoor relaxation.
Convenient, Cozy Home: Porches, Fire Pit, Office - Middletown, CT
No reviews

Convenient, Cozy Home: Porches, Fire Pit, Office

cottage, Meriden
This Meriden holiday cottage is situated within 5 kilometres of Cedar Park, Brookside Park, Columbus Park, the Andrews Homestead Museum, and the Connecticut Law Enforcement Memorial, with Meriden Station a short walk away.
This family-friendly property offers a fully equipped kitchen with a microwave and dishwasher, air conditioning, a garden with barbecue grills, an arcade/game room, and complimentary WiFi, alongside free on-site parking.
Modern 1br Near Wesleyan & Main Street - Middletown, CT
9.9 29 reviews

Modern 1br Near Wesleyan & Main Street

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.

Best Middletown, CT vacation rentals with parking

Cozy One Bedroom In-law Suite With Two Beds - Middletown, CT
No reviews

Cozy One Bedroom In-law Suite With Two Beds

apartment, Middletown
This one-bedroom flat is situated in central Middletown, offering excellent walkability to Middlesex Hospital (200 metres), Wesleyan University, and Main Street's amenities.
The apartment accommodates two guests and features air conditioning, parking, and a kitchen equipped with a fridge and microwave oven.
Guesthouse Farm Stay - Middletown, CT
10 342 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.
3 Br Apartment Near Wesleyan 202 - Middletown, CT
No reviews

3 Br Apartment Near Wesleyan 202

apartment, Middletown
This three-bedroom flat is located near Wesleyan University in Middletown, offering easy access to the university and the surrounding areas, with complimentary on-site parking and free WiFi.
This 93 square meter residence features air conditioning, a fully equipped kitchen with a dishwasher and oven, and can accommodate up to eight guests, with towels and bed linen provided.
Modern Middletown Retreat, Minutes To Downtown! - Middletown, CT
10 2 reviews

Modern Middletown Retreat, Minutes To Downtown!

apartment, Middletown
This apartment is conveniently located in Middletown, just 1.6 kilometres from Wesleyan University, Middlesex Hospital, and General Mansfield House, making it ideal for visitors with business or medical appointments. The surrounding area offers easy access to the Connecticut River and Harbor Park, both within 3.2 kilometres, providing scenic walks and outdoor activities.
The apartment is well-equipped with a fully furnished kitchen, including a microwave, dishwasher, and stovetop, perfect for self-catering. Guests can enjoy free parking and Wi-Fi, a fireplace for cosy evenings, and barbecue grills for outdoor dining.

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

Convenient, Cozy Home: Porches, Fire Pit, Office - Middletown, CT
No reviews

Convenient, Cozy Home: Porches, Fire Pit, Office

house, Meriden
This Meriden holiday home is located 12 kilometres from Wesleyan University and 35 kilometres from Tweed-New Haven Airport, with Lake Compounce and Yale University also nearby.
This spacious three-bedroom, four-bathroom property offers accommodation for up to 15 guests, featuring a fully equipped kitchen, a garden, a terrace, a fitness room, and a games room, with a floor area of 169 square metres.
Lovely 3 Bedroom Colonial Home - Middletown, CT
No reviews

Lovely 3 Bedroom Colonial Home

house, Middletown
Accommodation. This accommodation is based in Middletown.
Services and facilities include a kitchen, a dish washer and a terrace.
Waterfront Lake House - Middletown, CT
9.5 2 reviews

Waterfront Lake House

house, East Hampton
This East Hampton waterfront property offers direct lake access with water sports facilities, situated approximately 19 kilometres from Wesleyan University and 21 kilometres from the Goodspeed Opera House.
The 186-square-metre house boasts four bedrooms, two bathrooms, sleeps fifteen guests, and includes a fully equipped kitchen, free Wi-Fi, private parking, and a terrace.
Convenient, Cozy Home: Porches, Fire Pit, Office - Middletown, CT
No reviews

Convenient, Cozy Home: Porches, Fire Pit, Office

apartment, Meriden
This Meriden flat offers a central location, situated 9.6 kilometres from Powder Ridge and 14.4 kilometres from Choate Rosemary Hall, providing convenient access to ski slopes and university campuses.
This 169 square metre residence accommodates up to 8 guests across 3 bedrooms and 4 bathrooms, featuring amenities such as an arcade machine, cornhole set, screened porch with a gas fire pit, and a dedicated office space.

Best pet friendly Middletown, CT vacation rentals

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

New! Charming Riverside Home-ct River Private, Spacious, Family & Pet Friendly - Middletown, CT
10 17 reviews

New! Charming Riverside Home-ct River Private, Spacious, Family & Pet Friendly

apartment, Rocky Hill
This luxurious Rocky Hill waterfront apartment boasts breathtaking Connecticut River views and is situated a short distance from Ferry Park, offering easy access to Dinosaur State Park and the Connecticut Science Centre.
The 149 square metre (1600 sq ft) property features three bedrooms, three bathrooms, sleeps eight guests, and includes a chef's kitchen, a 84 square metre (900 sq ft) deck with a hot tub, and a detached garage.
Cabin Deck House - Formidable Cabin In Laurel Island - Middletown, CT
10 2 reviews

Cabin Deck House - Formidable Cabin In Laurel Island

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.
Brownstone Oasis - Middletown, CT
9.8 10 reviews

Brownstone Oasis

apartment, Portland
This Portland flat is located in a quiet area, offering easy access to the city centre and its attractions.
This two-bedroom, one-bathroom flat sleeps up to eight guests and includes a kitchen, air conditioning, a jacuzzi, and parking, making it a comfortable base for exploring Portland.
Fun On The Lake - Middletown, CT
10 3 reviews

Fun On The Lake

house, East Hampton
This three-bedroom house is situated in East Hampton, offering a tranquil setting just 19 kilometres from Wesleyan University.
The property boasts a spacious 204 square metre layout, accommodating up to 15 guests and featuring a fully equipped kitchen, a terrace, a garden, and parking.
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