Holiday Rentals in Middletown

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Middletown holiday rentals
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Middletown holiday rentals: compare the best deals

Best family friendly Middletown holiday rentals

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

Waterfront Lake House - Middletown
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.
Comfy And Equipped For A Small Family - Webster Hill Suite1e - Middletown
7.4 3 reviews

Comfy And Equipped For A Small Family - Webster Hill Suite1e

apartment, New Britain
This New Britain apartment is conveniently located close to the New Britain Museum of American Art and Hill-Stead Museum, making it a great base for exploring the city's cultural attractions. The surrounding area is quiet and residential, offering a peaceful retreat after a day of sightseeing.
The flat is a two-bedroom, one-bathroom property with a floor area of 60 square metres, comfortably accommodating up to three guests. It offers a range of amenities including a private kitchen, garden, and parking, as well as internet access and air conditioning.
Magnificent Riverfront Home, Completely Private.  Book  7 Nights Get 10% Off - Middletown
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.
Spacious 4-bedroom House On The Water! - Middletown
10 2 reviews

Spacious 4-bedroom House On The Water!

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.

Best Middletown holiday rentals with parking

Cozy Family Home-sleeps 6 Near Wesleyan & Weddings - Middletown
10 4 reviews

Cozy Family Home-sleeps 6 Near Wesleyan & Weddings

apartment, Middletown
This apartment is located in a secluded cul-de-sac in Middletown, offering privacy and easy access within 500 meters to Main Street's shops and eateries, Wesleyan University, and local wedding venues.
This accommodation sleeps six and features two newly renovated bathrooms, a dining area for six, an eat-in kitchen, and a spacious backyard, with flexible sleeping arrangements including two queen beds, a twin bed, a futon, and a daybed.
Cozy Cape Close To Farmington, Plainville & Downtown New Britain - Middletown
10 30 reviews

Cozy Cape Close To Farmington, Plainville & Downtown New Britain

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.
Beautiful Sunny Apartment In Historic Village - Middletown
9.7 263 reviews

Beautiful Sunny Apartment In Historic Village

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.
Simple Comfort And Tranquility - Middletown
No reviews

Simple Comfort And Tranquility

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.

Frequently asked questions about holiday rentals in Middletown

  • 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 and September to October. The weather is still pleasant during these months, but the crowds are smaller and the prices are lower.
  • What are the best Airbnb and vacation rentals in Middletown?

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

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

    Middletown hosts a variety of events throughout the year. The Middletown Arts Festival is a popular event in the summer, showcasing local artists and musicians. In the autumn, the Middletown Fall Festival features a parade, live music, and a craft fair. And if you're in town during the winter, be sure to check out the Middletown Holiday Festival, which features a tree lighting ceremony, carols, and Santa Claus.
  • What are the most popular Airbnbs in Middletown?

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

    Middletown has plenty of free and budget-friendly activities to offer. You can take a walk or bike ride along the scenic Connecticut River, visit the free exhibits at the Wesleyan University Art Museum, or explore the historic downtown area.
  • What are the best vacation rentals with a pool in Middletown?

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

    For a taste of Middletown's local cuisine, you should definitely check out the Silver Star Restaurant. They're known for their classic American dishes, including their famous burgers and fries. If you're looking for something a bit more upscale, the A Mano Restaurant is a great choice, with its focus on fresh, seasonal ingredients.
  • What are the best rentals for families and kids in Middletown?

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

    The Mattabesett Trail is a popular walking and cycling route that runs through Middletown. It's a scenic trail that follows the Mattabesett River and offers beautiful views of the surrounding countryside. For a shorter, more urban walk, you can explore the downtown area and its historic streets.
  • What are the best rentals or Airbnbs with a jacuzzi in Middletown?

  • Are there pet-friendly attractions in Middletown, CT?

    Many of Middletown's parks and gardens are pet-friendly. The Wadsworth Mansion allows well-behaved dogs on leashes in its gardens, and the Long Hill Estate and Gardens also welcomes furry friends. You can also find pet-friendly restaurants and cafes in the downtown area.
  • What are the benefits of choosing a vacation rental in Middletown, CT?

    Vacation rentals in Middletown offer more space and privacy than hotels, often at a lower cost. They also provide access to kitchens and laundry facilities, which can be convenient for families or longer stays. You might also enjoy the unique character and charm of a home away from home.
  • What are the top sports attractions and facilities in Middletown, CT?

    Middletown is home to several sports facilities, including the Wesleyan University athletic fields and the Middletown YMCA. The city also hosts a variety of sporting events, including high school football games and the annual Middletown Marathon.

Popular destinations

Best Middletown holiday rentals with a balcony

Fun On The Lake: Games, Dock, Slide, Ev Charger - Middletown
10 23 reviews

Fun On The Lake: Games, Dock, Slide, Ev Charger

apartment, East Hampton
This waterfront holiday home is situated in Lake Pocotopaug, a neighbourhood in East Hampton, Connecticut, just a 5-minute drive from grocery stores and a 3-minute walk from a Middlesex Land Trust park with trails.
The 203 square metre property boasts three bedrooms, three bathrooms, and a guest capacity of eight, with a modern kitchen, two living rooms, a converted garage game room with a pool table and ping pong table, and a fire pit for roasting marshmallows.
Fun On The Lake - Middletown
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.
Convenient, Cozy Home: Porches, Fire Pit, Office - Middletown
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.
3 Bedrooms Fully Finished - Middletown
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.

Best pet friendly Middletown holiday rentals

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

Spacious And Quiet - Middletown
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.
1 Min To I-91  - Newly Renovated Modern 2 Br Home - Middletown
No reviews

1 Min To I-91 - Newly Renovated Modern 2 Br Home

apartment, Berlin
This Berlin flat is conveniently located a 6.4-kilometre drive from New Britain Stadium and an 8-kilometre drive from Cromwell Commons Shopping Centre, with proximity to attractions such as Iwo Jima Survivors Memorial Park and Dinosaur State Park.
This apartment offers space for four guests with a fully equipped kitchen, air conditioning, free Wi-Fi, and on-site parking, while nearby recreational spots include Brownstone Exploration & Discovery Park and Crystal Bees Bowling.
2br Apartment Near Wesleyan 102 - Middletown
9.0 4 reviews

2br Apartment Near Wesleyan 102

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.
3 Br Apartment Near Wesleyan 201 - Middletown
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.
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