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.

2br Apartment Near Wesleyan 301 - Middletown, CT
8.8 8 reviews

2br Apartment Near Wesleyan 301

apartment, Middletown
This spacious third-floor flat is located in Middletown, just 200 metres from Wesleyan University, making it ideal for those visiting the academic institution.
This pet-friendly accommodation for up to four guests offers two bedrooms, one bathroom, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, parking, and an on-site washer and dryer.
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.
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.

Best Middletown, CT holiday rentals with air conditioning

Cozy 2 Bdrm 1 Bthrm Apartment With Wi-fi, Parking - Middletown, CT
9.6 80 reviews

Cozy 2 Bdrm 1 Bthrm Apartment With Wi-fi, Parking

apartment, Middletown
This two-bedroom flat is situated in a peaceful residential neighbourhood in Middletown, just 6km from the city centre and 5km from Wesleyan University. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The flat can comfortably accommodate up to four guests and features a well-equipped kitchen with a fridge, microwave oven, and dishwasher. Guests can also enjoy access to a garden, parking, air conditioning, and the convenience of internet access.
Sunny Private 1 Bedroom Apartment - Middletown, CT
9.8 570 reviews

Sunny Private 1 Bedroom Apartment

apartment, Portland
This one-bedroom flat is conveniently located in Portland, just 5-10 kilometres from Wesleyan University, Downtown Middletown, Middlesex Hospital, and Saint Clements Castle. The apartment has received excellent ratings for cleanliness, location, and user experience.
The flat can accommodate up to 3 guests and features a well-equipped kitchen with a fridge and microwave oven, air conditioning, parking, and internet access. Guests can enjoy a modern and traditional design, a dedicated reading nook/office, and easy access to local attractions and amenities.
Cozy In-law Near Wesleyan - Clean And Private - Middletown, CT
10 5 reviews

Cozy In-law Near Wesleyan - Clean And Private

apartment, Middletown
This private in-law flat, offering a separate entrance for enhanced privacy, is located in a quiet neighbourhood just 7 minutes by car from central Middletown, Wesleyan University, and local shops and restaurants.
This self-contained studio boasts a king-size pull-out sofa, a fully equipped kitchenette with a fridge, an in-unit washer/dryer, air conditioning, and free on-site parking, accommodating up to two guests.
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.

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.

Fun On The Lake: Games, Dock, Slide, Ev Charger - Middletown, CT
10 24 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.
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.
Lovely 3 Bedroom Colonial Home - Middletown, CT
No reviews

Lovely 3 Bedroom Colonial Home

house, Middletown
House rental listing. You will stay in Middletown.
Facilities and services include an iron, free parking and a terrace.
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.

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.

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.
Spacious Studio With Ac And Wifi In Charming Durham - Middletown, CT
10 9 reviews

Spacious Studio With Ac And Wifi In Charming Durham

studio, Durham
This Durham studio apartment is situated in a rural location, conveniently close to attractions such as the Artfarm and Toyota Oakdale Theatre, with the General Mansfield House and Wadsworth Mansion within a reasonable driving distance.
The self-catering apartment, sleeping up to two guests, features a fully equipped kitchen with dishwasher and crockery, a spacious deck with BBQ, and amenities including high-speed Wi-Fi, air conditioning, and a comfortable bathroom.
Cozy Comforts! - Middletown, CT
10 161 reviews

Cozy Comforts!

apartment, Haddam
This one-bedroom flat is peacefully located just a few minutes' drive from Middletown town centre and Wesleyan University, with the Connecticut shoreline around 32 kilometres away. The fully renovated property offers a modern open-plan living space, a private entrance, off-street parking, and a garden, ideal for a couple seeking a comfortable and convenient base to explore the area.
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.

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.

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

Cozy Historic Home Guest Suite

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

Clover Nook

apartment, Middletown
Modern Middletown Retreat, Minutes To Downtown! - Middletown, CT
9.6 14 reviews

Modern Middletown Retreat, Minutes To Downtown!

apartment, Middletown
Cozy Family Home-sleeps 6 Near Wesleyan & Weddings - Middletown, CT
10 8 reviews

Cozy Family Home-sleeps 6 Near Wesleyan & Weddings

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.

Private Apartment I Near Wesleyan University - Middletown, CT
9.1 309 reviews

Private Apartment I Near Wesleyan University

apartment, 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.

Brownstone Oasis - Middletown, CT
9.8 10 reviews

Brownstone Oasis

apartment, Portland
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
Private Apt In Middletown-wesleyan 101 - Middletown, CT
No reviews

Private Apt In Middletown-wesleyan 101

apartment, Middletown
3 Br Apartment Near Wesleyan 202 - Middletown, CT
No reviews

3 Br Apartment Near Wesleyan 202

apartment, Middletown

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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