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

Belltown House At Airline Trail - Middletown, CT
No reviews

Belltown House At Airline Trail

apartment, East Hampton
This East Hampton flat offers a prime countryside and waterfront location, a mere 2-minute drive from Lake Pocotopaug and 6 minutes from Day Pond State Park, with convenient access to boating centres and cultural sites like the Goodspeed Opera House.
Spanning 86 square metres, this family-friendly dwelling accommodates up to six guests across three bedrooms and one bathroom, featuring a fully equipped kitchen and onsite parking for exploring the surrounding areas.
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.
Magnificent Riverfront Home, Completely Private.  Book  7 Nights Get 10% Off - Middletown, CT
9.8 122 reviews

Magnificent Riverfront Home, Completely Private. Book 7 Nights Get 10% Off

apartment, East Hampton
This beachfront house is located in Middle Haddam, just 3 kilometres from Dart Island State Park and the Connecticut River, offering a peaceful retreat with easy access to nature. The house has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This 5-bedroom property spans 344 square metres and comfortably accommodates up to 9 guests. The house offers a range of amenities for a relaxing stay, including a fully equipped kitchen, a jacuzzi, a terrace, a garden, and 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

Charming 1br Retreat | Free Parking + Wifi C5 - Middletown, CT
9.8 46 reviews

Charming 1br Retreat | Free Parking + Wifi C5

apartment, Wallingford
This Wallingford apartment is located just 22 kilometres from Yale University and 24 kilometres from New Haven City Hall, offering a peaceful retreat from the bustle of the city. It has received excellent ratings for location, cleanliness, and overall user experience.
The one-bedroom flat is 51 square metres and can accommodate up to two guests. It features a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, parking, and free Wi-Fi, making it a comfortable and convenient choice for travellers.
Stylish Stay Near Wesleyan - 2br - Middletown, CT
9.4 20 reviews

Stylish Stay Near Wesleyan - 2br

apartment, Middletown
This Middletown apartment, ideally located minutes from Wesleyan University and Main Street, offers easy access to shops, restaurants, and cultural attractions.
The two-bedroom, one-bathroom flat sleeps four, includes high-speed internet, a washer/dryer, and is fully furnished for a comfortable stay.
3 Br Apartment Near Wesleyan 202 - Middletown, CT
8.0 1 review

3 Br Apartment Near Wesleyan 202

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.
Seasons Hospitality Offers All New 1br With Tons Of Charm - Middletown, CT
10 1 review

Seasons Hospitality Offers All New 1br With Tons Of Charm

apartment, Wallingford
This Wallingford apartment, conveniently located near the Toyota Oakdale Theatre and Eli Whitney Museum, offers easy access to local attractions and shopping at Maplecroft Plaza.
The 79 square metre self-catering flat features one bedroom, one bathroom, and sleeps two guests, boasting a fully equipped kitchen, free laundry facilities, and a large flat-screen TV.

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 Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Middletown, CT
9.6 13 reviews

Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger

apartment, Haddam
This waterfront property is located in Killingworth, Connecticut, just a short distance from Cockaponset State Forest and Sundial Herb Garden, offering easy access to nature and local attractions. The property has received excellent guest ratings, highlighting its comfortable and enjoyable stay.
This four-bedroom house spans 121 square metres and comfortably accommodates up to 10 guests. It features a fully equipped kitchen, a terrace, a garden, and parking, providing everything you need for a relaxing and enjoyable stay.
3 Br Apartment Near Wesleyan 201 - Middletown, CT
10 1 review

3 Br Apartment Near Wesleyan 201

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.
#29 - Modern 5 Bedroom/2 Bath - Middletown, CT
9.4 6 reviews

#29 - Modern 5 Bedroom/2 Bath

apartment, Middletown
This five-bedroom Middletown apartment, ideally located near Wadsworth Falls State Park and the Connecticut Valley Railroad State Park Trail, offers convenient access to Middletown's attractions.
The 158-square-metre (approximately 1700 square feet) property features a spacious layout with two living rooms, accommodating up to ten guests, and includes amenities such as a fully equipped kitchen, high-speed internet (500mbps), and a terrace.
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.

Best pet friendly Middletown, CT vacation rentals

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

3 Br Apartment Near Wesleyan 201 - Middletown, CT
8.7 9 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.
Lakeside Treasure Boating Swimming Kayaking - Middletown, CT
10 4 reviews

Lakeside Treasure Boating Swimming Kayaking

apartment, East Hampton
This waterfront flat in East Hampton's Lake Pocotopaug district offers direct access to the bay beach, a mere 100 metres away, and is close to historical sites such as Comstock Bridge and Amasa Day House.
This property, suitable for up to five guests, features one bedroom and one bathroom, with amenities including air conditioning, Wi-Fi, and on-site laundry, and is conveniently located within 10 kilometres of attractions like Marlborough Arts Centre and Brownstone Exploration & Discovery Park.
#42 - Stunning Modern 2 Br Home - 2 Min From Hwy - Middletown, CT
8.8 15 reviews

#42 - Stunning Modern 2 Br Home - 2 Min From Hwy

apartment, Berlin
This Berlin flat offers excellent access to major motorways, placing you just 100 metres from the Berlin Turnpike's shops and restaurants.
This contemporary accommodation features two bedrooms, one bathroom, and a guest capacity of four, boasting a spacious open-plan living area, a fully equipped modern kitchen, and a large rear deck for outdoor enjoyment, with parking readily available.
Cozy Cape On Farmington & Plainville Border - Middletown, CT
10 30 reviews

Cozy Cape On Farmington & Plainville Border

apartment, New Britain
This charming four-bedroom home is located in New Britain, just a short five-minute drive from the revitalised downtown area with its eclectic coffee shops, bars, and restaurants. The property has received excellent ratings for location, cleanliness, and overall user experience.
The spacious 111 square metre apartment offers a comfortable and convenient stay for families or groups. Guests will enjoy a fully equipped kitchen, modern amenities like a coffee machine, fast Wi-Fi, a smart TV, and Alexa voice control, as well as a themed bedroom for each member of the group.
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