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

Discover Central Holiday Rentals in Middletown, CT

Reconnect deeply with your significant other at peaceful holiday rentals for couples in Middletown, CT, offering romantic, quiet settings.

1r Private Downtown Oasis - Middletown, CT
9.8 154 reviews

1r Private Downtown Oasis

apartment, Middletown
This charming flat is situated just one block from Wesleyan University and the main street in Middletown, CT, offering easy access to the vibrant downtown area and the university's events. It has consistently received excellent ratings for location, cleanliness, and user experience.
The apartment is located on the first floor of a historic home and can accommodate up to four guests. It features a fully equipped kitchen, a private patio and fenced-in backyard, a washer/dryer, and wireless internet, making it a comfortable and convenient base for exploring the area.
Quaint 2br Apt- 1 Block Walk To Wesleyan & Main St - Middletown, CT
9.9 909 reviews

Quaint 2br Apt- 1 Block Walk To Wesleyan & Main St

apartment, Middletown
This two-bedroom flat is located in the heart of Middletown, just 0.8 km from Wesleyan University and 0.4 km from Main Street, offering easy access to shops, restaurants, and entertainment venues. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The flat is ideal for a group of up to 5 guests and features a modern kitchen equipped with a dishwasher, a cosy living area, and a small backyard for relaxation. Guests can enjoy amenities such as a TV with Roku, a DVD player, and access to a shared laundry facility.
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.
Beautiful Sunny Apartment In Historic Village - Middletown, CT
9.7 265 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.

Best Middletown, CT holiday rentals with air conditioning

Cozy Newly Remodeled Home Close To Major Amenities  In Connecticut A - Middletown, CT
9.2 130 reviews

Cozy Newly Remodeled Home Close To Major Amenities In Connecticut A

apartment, Middletown
This charming home is situated in Middletown, conveniently close to several notable landmarks. It has received excellent ratings for location, cleanliness, and overall user experience.
The property features a single bathroom and a well-equipped kitchen with a fridge. Enjoy the convenience of parking, air conditioning, internet access, and a garden.
Cozy Family Home-sleeps 6 Near Wesleyan & Weddings - Middletown, CT
10 8 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.
Bright And Cozy 2br Family Home - Middletown, CT
10 2 reviews

Bright And Cozy 2br Family Home

apartment, Middletown
This two-bedroom flat is located in a well-lit and spacious area of Middletown, offering convenient access to local attractions.
This property accommodates up to six guests and features a bright, spacious living area, a separate dining room, and a well-equipped kitchen with an island seating four, alongside a queen bedroom and a twin bunk room, all with ample closet space.
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.

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.

Popular destinations

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.

3 Br Apartment Near Wesleyan 201 - Middletown, CT
10 1 review

3 Br Apartment Near Wesleyan 201

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.
Private Apartment  In Berlin - Middletown, CT
9.0 7 reviews

Private Apartment In Berlin

apartment, Berlin
This Berlin holiday home is situated 2.9km from New Britain Stadium and 4km from Putter's Paradise Mini Golf, offering easy access to Berlin Station (a 13-minute walk).
The 111 square metre property sleeps four guests in two bedrooms and one bathroom, boasting amenities including a fully equipped kitchen, free Wi-Fi, a Smart TV, and on-site parking, plus a playground.
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.
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.

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.

Cozy Dog Friendly Updated House In Quiet Village Adjacent To Park - Middletown, CT
10 58 reviews

Cozy Dog Friendly Updated House In Quiet Village Adjacent To Park

apartment, North Branford
This North Branford holiday home, situated near Gouveia Winery (4.2km) and within 9.7km of Paradise Hills Vineyard and Tradition Golf Club, offers a tranquil rural escape.
The 150 square metre property boasts three bedrooms, three bathrooms, sleeps ten guests, and includes a fully equipped kitchen, Wi-Fi, a terrace, garden, spa, and parking.
Spacious 4-bedroom House On The Water! - Middletown, CT
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.
2br Apartment Near Wesleyan 301 - Middletown, CT
No reviews

2br Apartment Near Wesleyan 301

apartment, Middletown
This two-bedroom flat is located on the third floor in central Middletown, a stone's throw from Wesleyan University and within 500 meters of local shops and restaurants.
This pet-friendly residence accommodates up to four guests, offering a fully equipped kitchen, on-site laundry, air conditioning, and parking, with a strict policy against loud parties to ensure a quiet atmosphere.
Modern Middletown Retreat, Minutes To Downtown! - Middletown, CT
9.6 14 reviews

Modern Middletown Retreat, Minutes To Downtown!

apartment, Middletown
This three-bedroom apartment is located just a short distance from Wesleyan University in Middletown, within a 5km drive of Wadsworth Falls State Park. It has been rated excellent by previous guests.
This spacious 139 square metre dwelling can comfortably accommodate up to six guests. It comes equipped with a modern kitchen, a shared outdoor space, a spa, and high-speed internet access, making it ideal for families or groups of friends.

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.

Hot Tub And Pool Home Away From Home - Middletown, CT
9.9 59 reviews

Hot Tub And Pool Home Away From Home

apartment, Middletown
Clover Nook - Middletown, CT
10 4 reviews

Clover Nook

apartment, Middletown
Cozy Comforts! - Middletown, CT
10 161 reviews

Cozy Comforts!

apartment, Haddam
Historic Home 3 Mi To Middletown Main Street - Middletown, CT
10 3 reviews

Historic Home 3 Mi To Middletown Main Street

apartment, Middletown

Check Out 5-Star Self-Catering Holiday Rentals in Middletown, CT

Comfort, quality, and a prime location - each luxury holiday rental or Airbnb in Middletown, CT is selected with these standards in mind. Pick your favourite today.

Cozy Historic Home Guest Suite - Middletown, CT
9.8 73 reviews

Cozy Historic Home Guest Suite

house, Middletown

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.

2br Apartment Near Wesleyan 102 - Middletown, CT
8.8 5 reviews

2br Apartment Near Wesleyan 102

apartment, Middletown
Modern, Luxurious 3br New Build In Central Ct-stunning And Close To Everything! - Middletown, CT
10 2 reviews

Modern, Luxurious 3br New Build In Central Ct-stunning And Close To Everything!

apartment, Cromwell
Ct River Retreat - Modern Home With Ct River Views - Middletown, CT
10 66 reviews

Ct River Retreat - Modern Home With Ct River Views

apartment, East Hampton
Brownstone Oasis - Middletown, CT
9.8 10 reviews

Brownstone Oasis

apartment, Portland

Compare Holiday Rentals with a Pool in Middletown, CT

Having a pool at your holiday rental in Middletown, CT opens up a proper swim in the heart of the city without extra planning. Start comparing.

Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University - Middletown, CT
9.8 17 reviews

Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University

apartment, Middletown

Guest-Favourite Holiday Rentals with a Hot Tub in Middletown, CT

A holiday rental with a hot tub in Middletown, CT is perfect for unwinding in private after exploring the city. Browse our top-rated options.

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
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