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

Best family friendly Middletown, CT holiday rentals

Among the 100 accommodations in Middletown, CT, here are the 4 best family friendly rentals

Fun On The Lake: Games, Dock, Slide, Ev Charger - Middletown, CT
10 22 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.
Amazing Lakefront Property - Middletown, CT
9.4 30 reviews

Amazing Lakefront Property

apartment, Middlefield
This waterfront property is located just 2 kilometres from Lake Beseck Beach, Powder Ridge Mountain Park and Resort, and Lyman Orchards, offering easy access to a range of attractions and outdoor activities. It has received excellent user ratings, making it a popular choice for travellers.
The house offers 4 bedrooms and 4 bathrooms across a spacious 316 square metres, comfortably accommodating up to 10 guests. Enjoy the garden, barbecue grills, and balcony, along with modern amenities like free WiFi, a fireplace, and a fully equipped kitchen.
Guesthouse Farm Stay - Middletown, CT
10 332 reviews

Guesthouse Farm Stay

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.
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.

Best Middletown, CT holiday rentals with parking

Brownstone Oasis - Middletown, CT
10 5 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.
Grammy's Famous Lake House Retreat - Middletown, CT
9.8 9 reviews

Grammy's Famous Lake House Retreat

house, East Hampton
Grammy's Lake House is situated in East Hampton, New York, approximately 19 kilometres from both Wesleyan University and the Goodspeed Opera House.
This three-bedroom, two-bathroom property boasts 11 square metres of floor space, sleeps up to 13 guests, and features private waterfront access, a garden with outdoor play equipment, and free Wi-Fi.
3 Br Apartment Near Wesleyan 202 - Middletown, CT
9.6 5 reviews

3 Br Apartment Near Wesleyan 202

apartment, Middletown
This three-bedroom flat in Middletown offers a prime location, just a short distance from Wesleyan University, making it ideal for visitors to the area.
With capacity for six guests, this pet-friendly accommodation includes a fully equipped kitchen, air conditioning, and a garden, suitable for both short and extended stays.
Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University - Middletown, CT
9.8 15 reviews

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

apartment, Middletown
This Middletown holiday home boasts a mountainside location, within 5km of Smith Park and Falcon Field, and 10km of Kidcity Children's Museum and Wadsworth Falls State Park.
The 325 square metre property sleeps six guests across three bedrooms and four bathrooms, offering a swimming pool, jacuzzi, fitness centre, and free Wi-Fi alongside a fully equipped kitchen.

Frequently asked questions about holiday rentals in Middletown, CT

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

    The Connecticut Valley Railroad is always a hit with families, and the kiddos will love the interactive exhibits at the Connecticut Science Center. If it's a nice day, head to the Rockfall State Park for some outdoor fun.
  • 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 Cozy - Pet-friendly Apartment Near University 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 your vacation rental in advance, especially if you're planning to visit during peak season, which is from June to August. If you're looking for a quieter trip, consider visiting during the shoulder seasons, in the spring or autumn.
  • What are the most popular Airbnbs in Middletown, CT?

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

    The annual Middletown Arts Festival is a great event to catch, and there are also plenty of smaller festivals and events throughout the year. Check the Middletown website for a full list of events.
  • What are the best vacation rentals with a pool in Middletown, CT?

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

    Take a walk along the Connecticut River, explore the gardens at the Wadsworth Mansion, or visit the Russell Library for free. You can also find some great deals on food and drinks at the local restaurants.
  • What are the best rentals for families and kids in Middletown, CT?

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

    The Main Street Cafe is a great spot for classic American comfort food. For something a little more upscale, try the A Mano, which serves modern Italian cuisine. And for something a bit more casual, head to the Little Grill on the Avenue for some delicious burgers and fries.
  • 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 Mattabesett Trail is a great option for a scenic walk or bike ride. You can also explore the historic downtown area, which is full of charming shops and restaurants.
  • Are there pet-friendly attractions in Middletown, CT?

    Many of the parks in Middletown are dog-friendly, including the Rockfall State Park. You can also find some pet-friendly restaurants and shops in the downtown area.
  • What are the benefits of choosing a vacation rental in Middletown, CT?

    Vacation rentals offer more space and privacy than a hotel room. They're also a great option for families or groups of friends travelling together. You can often find vacation rentals with kitchens, which allows you to save money on dining out.
  • What are the top sports attractions and facilities in Middletown, CT?

    Middletown is home to the Wesleyan University athletic facilities, which include a football stadium, a baseball field, and a tennis complex. There are also several public parks with sports fields and courts.

Popular destinations

Best Middletown, CT holiday rentals with a balcony

#28- *Modern Bungalow* - Middletown, CT
8.8 3 reviews

#28- *Modern Bungalow*

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.
24 Serenity A Lakefront Cottage Retreat - Middletown, CT
No reviews

24 Serenity A Lakefront Cottage Retreat

house, Middletown
This Middletown lakefront cottage, situated 4.3km from Wesleyan University and within a 19-24km radius of Central Connecticut State University, the Wadsworth Atheneum, and the Bushnell Center for the Performing Arts, offers serene lake views and easy access to local attractions.
The 62 square metre property features one bathroom, accommodates seven guests, and includes a fully equipped kitchen, private balcony, washing machine, air conditioning, Wi-Fi, and pet-friendly access.
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.

Best pet friendly Middletown, CT holiday rentals

Among the 100 accommodations in Middletown, CT, here are the 4 best pet friendly rentals

3 Br Apartment Near Wesleyan 201 - Middletown, CT
No reviews

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

3 Br Apartment Near Wesleyan 202

apartment, Middletown
This three-bedroom flat is located near Wesleyan University in Middletown, offering easy access to the university and the surrounding areas, with complimentary on-site parking and free WiFi.
This 93 square meter residence features air conditioning, a fully equipped kitchen with a dishwasher and oven, and can accommodate up to eight guests, with towels and bed linen provided.
29 - Modern 5 Bedroom 2 Bath - Middletown, CT
No reviews

29 - Modern 5 Bedroom 2 Bath

house, Middletown
This modern five-bedroom house is located in Middletown, Connecticut, 6 kilometres from Wesleyan University.
The 157-square-metre property sleeps up to 19 guests and boasts a fully equipped kitchen, two bathrooms, a garden, and free Wi-Fi; in-unit laundry facilities are also available.
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.
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