Holiday Rentals in Middletown, CT

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Middletown, CT holiday rentals
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Best Holiday rentals and Airbnb offers in Middletown, CT

Explore Holiday Rentals for Families in Middletown, CT

Travelling to Middletown, CT with children? A quality family holiday rental or Airbnb makes everything easier with city attractions nearby.

Modern 1br Near Wesleyan & Main Street - Middletown, CT
9.9 22 reviews
Middletown, CT
30/06 – 02/07
£175/nighttotal: £350 (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.
Guesthouse Farm Stay - Middletown, CT
10 313 reviews
Middletown, CT
30/06 – 02/07
£153/nighttotal: £306 (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.
Spacious 4-bedroom House On The Water! - Middletown, CT
Middletown, CT
30/06 – 02/07
£393/nighttotal: £786 (2 )

Spacious 4-bedroom House On The Water!

4 2
apartment , Meriden
This Meriden house offers a tranquil retreat on Beaver Pond, conveniently located near theme parks and local attractions like Safari Golf.
This family-friendly apartment provides four bedrooms, two bathrooms, and accommodation for up to eight guests, featuring a deck overlooking Beaver Pond, a fully equipped kitchen, air conditioning, and proximity to outdoor activities such as kayaking and hiking.
Updated 2-bedroom Near Wesleyan-middletown - Middletown, CT
9.9 95 reviews
Middletown, CT
30/06 – 02/07
£193/nighttotal: £386 (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.

Choose the Right Self-Catering Holiday Rentals with Free Parking in Middletown, CT

Park up and enjoy the city centre. These holiday rentals in Middletown, CT come with a free car park on-site. Start comparing now.

Gorgeous 3-bedroom Apartment In New Britain With Wifi, Ac - Middletown, CT
10 1 review
Middletown, CT
30/06 – 02/07
£249/nighttotal: £498 (2 )

Gorgeous 3-bedroom Apartment In New Britain With Wifi, Ac

3 2
apartment , New Britain
This three-bedroom New Britain apartment, ideal for families or groups of up to six, is conveniently located near Central Connecticut State University and major roadways, offering easy access to attractions such as the Timberlin Golf Course and Lake Compounce (distances not specified).
The self-catering property features a fully equipped kitchen with a microwave, air conditioning, and a modern living room with streaming services; nearby amenities include restaurants and shopping centres.
Cabin Deck House - Formidable Cabin In Laurel Island - Middletown, CT
10 2 reviews
Middletown, CT
30/06 – 02/07
£617/nighttotal: £1234 (2 )

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.
New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown. - Middletown, CT
9.8 27 reviews
Middletown, CT
30/06 – 02/07
£700/nighttotal: £1400 (2 )

New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown.

4 2
apartment , Durham
This Durham holiday home is situated approximately 2.3 kilometres from Millers Pond State Park, and within 10 kilometres of Ron McCutcheon Park and Tri-Mountain State Park, offering easy access to local recreational areas and Lyman Orchards.
The four-bedroom property sleeps eight guests, boasting three bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, a terrace, garden, parking, and free Wi-Fi; enjoy a comfortable stay with amenities such as a fireplace and barbecue facilities.
Spacious 5-bedroom Family Home - Middletown, CT
Middletown, CT
27/06 – 04/07
£266/nighttotal: £1862 (7 )

Spacious 5-bedroom Family Home

1 2
apartment , New Britain
This New Britain flat is located 35 kilometres from Bradley International Airport.
This one-bedroom flat for up to 19 guests offers complimentary WiFi, private parking, and a fully equipped kitchen, with air conditioning and a flat-screen TV provided.

Frequently asked questions about holiday rentals in Middletown, CT

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

    The Connecticut River Museum is always a big hit with families, especially the interactive exhibits. For a day outdoors, head to the Wadsworth Falls State Park, there's plenty of space to run around and trails to explore. If you're looking for something a bit different, the Oakdale Theatre hosts a range of family-friendly events throughout the year.
  • What are the best Airbnb and holiday rentals in Middletown, CT?

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

    The best time to book a vacation rental in Middletown is during the shoulder seasons, from April to May or September to October. You'll avoid the crowds and the prices will be lower, but you'll still have plenty of sunshine and warm weather.
  • What are the most popular Airbnbs in Middletown, CT?

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

    The Middletown Arts Festival in June is a great event, with live music, art displays, and food stalls. In August, the city hosts the annual Middletown Street Fair, which features a parade, live music, and a variety of vendors. A bit further afield, the annual Essex Steam Train & Riverboat Excursion is a popular event.
  • What are the best holiday rentals with a pool in Middletown, CT?

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

    A walk along the Connecticut River Walk is a great way to spend a few hours, it's completely free and offers stunning views of the river. The Russell Library is also free to enter and has a range of exhibits and events throughout the year. If you're looking for something a bit more active, the city has a number of free parks and playgrounds.
  • What are the best rentals for families and kids in Middletown, CT?

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

    For a taste of New England, head to The Black Sheep, they have a fantastic selection of local seafood. If you're looking for something a bit more casual, try The Pantry for a delicious breakfast or lunch. The Stone Soup is a great spot for a more formal meal.
  • 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 Connecticut River Walk is a great option for walking or cycling, it stretches for several miles along the river and offers stunning views. For a more challenging ride, try the Mattabesett Trail, which winds its way through the countryside.
  • Are there pet-friendly attractions in Middletown, CT?

    Many of the parks in Middletown are pet-friendly, including the Wadsworth Falls State Park and the Harbor Park. The Connecticut River Museum also welcomes well-behaved dogs on a leash.
  • What are the benefits of choosing a vacation rental in Middletown, CT?

    Vacation rentals offer more space and privacy than hotels. They're often located in more residential areas, which can give you a better feel for the local community. Plus, you can often save money by cooking your own meals.
  • What are the top sports attractions and facilities in Middletown, CT?

    Middletown is home to the Wesleyan University athletic facilities, which include a state-of-the-art stadium and a variety of sports fields. The city also has a number of public parks with tennis courts, basketball courts, and playgrounds. For golf enthusiasts, the Middletown Golf Course offers a challenging 18-hole course.

Destinations nearby

Best Self-Catering Holiday Rentals with a Terrace in Middletown, CT

Private balconies with city skyline views come as standard at these holiday rentals in Middletown, CT for a lovely start to your day.

#24 *Serenity* A Lakefront Cottage Retreat - Middletown, CT
9.8 23 reviews
Middletown, CT
30/06 – 02/07
£259/nighttotal: £518 (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.
3 Br Apartment Near Wesleyan 201 - Middletown, CT
Middletown, CT
30/06 – 02/07
£249/nighttotal: £498 (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.
Fashionably Cozy Place - Middletown, CT
8.2 10 reviews
Middletown, CT
13/07 – 10/08
£149/nighttotal: £4172 (28 )

Fashionably Cozy Place

2 3
apartment , Meriden
This two-bedroom apartment is situated in Meriden, conveniently located 16 km from Wesleyan University, 22 km from Lake Compounce, and 22 km from Central Connecticut State University. The surrounding area is peaceful and offers easy access to attractions, making it a great base for exploring the region. This property has received excellent ratings for cleanliness and location, ensuring a comfortable and enjoyable stay.
The 121 square metre apartment comfortably sleeps six guests and features a fully equipped kitchen with a fridge and microwave, as well as air conditioning, free Wi-Fi, and parking. It is ideal for families or groups looking for a self-contained accommodation with a range of amenities, and is perfect for exploring Meriden and its surroundings.
#28- *Modern Bungalow* - Middletown, CT
8.8 3 reviews
Middletown, CT
13/07 – 10/08
£203/nighttotal: £5684 (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.

Popular Pet-Friendly Holiday Rentals in Middletown, CT

No need to leave your dog behind in Middletown, CT. Our holiday rentals offer proximity to dog parks and lovely city walks.

3 Br Apartment Near Wesleyan 201 - Middletown, CT
10 1 review
Middletown, CT
30/06 – 02/07
£239/nighttotal: £478 (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.
Spacious And Quiet - Middletown, CT
8.0 7 reviews
Middletown, CT
13/07 – 10/08
£154/nighttotal: £4312 (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.
2br Apartment Near Wesleyan 301 - Middletown, CT
10 2 reviews
Middletown, CT
13/07 – 10/08
£209/nighttotal: £5852 (28 )

2br Apartment Near Wesleyan 301

2 3
apartment , Middletown
This flat offers a prime location in Middletown's Washington Street Historic District, just 700 metres from Kidcity Children's Museum and a 1.3 kilometre walk to Harbor Park.
This 88 square metre accommodation sleeps four guests and features two bedrooms, one bathroom, air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher, and on-site parking.
Apartment In Middletown-wesleyan 301 - Middletown, CT
9.0 1 review
Middletown, CT
13/07 – 10/08
£179/nighttotal: £5012 (28 )

Apartment In Middletown-wesleyan 301

1 3
apartment , Middletown
This Middletown-Wesleyan 301 flat is situated in Middletown, a mere 550 metres from Wesleyan University, and 21 kilometres from Central Connecticut State University.
This residence offers 88 square metres of living space with two bedrooms, a fully equipped kitchen, and capacity for six guests, complete with complimentary on-site parking and Wi-Fi.
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