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

Brownstone Oasis - Middletown, CT
9.8 10 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.
(King Bed) Close To Midstate - Middletown, CT
9.3 3 reviews

(King Bed) Close To Midstate

apartment, Meriden
This Meriden apartment, ideal for families, offers two bedrooms and one bathroom, comfortably sleeping five guests and includes a fully equipped kitchen, in-unit laundry, and a 60-inch flat-screen TV with streaming services.
The property boasts a newly remodelled bathroom, hardwood floors, and smart locks, alongside the convenience of early check-in/check-out (fee applies), but its precise location within Meriden is unspecified.
Cozy Dog Friendly Updated House In Quiet Village Adjacent To Park - Middletown, CT
10 59 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.
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.

Best Middletown, CT holiday rentals with parking

The Studio Apartment - Middletown, CT
9.7 36 reviews

The Studio Apartment

apartment, Meriden
This studio apartment in Meriden is conveniently located for exploring local attractions.
This one-bedroom accommodation for up to three guests features a hot tub, a 75-inch TV with an Xbox Series console, and an arcade machine, with parking and internet provided.
All New Fully Furnished Cozy Studio - Middletown, CT
9.8 8 reviews

All New Fully Furnished Cozy Studio

studio, Wallingford
This Wallingford centre flat is conveniently located a 7-minute walk from Wallingford railway station, 15 minutes from the Wallingford Public Library and Choate Rosemary Hall, and within 1.6km of Masonicare Health Centre and the Paul Mellon Arts Centre.
The 45 square metre apartment offers one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, in-unit laundry, and on-site parking.
Delightful And Cozy Home In Middletown - Middletown, CT
9.3 128 reviews

Delightful And Cozy Home In Middletown

house, 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.
Quiet 2 Bed Room Apt W/ Private Entrance. - Middletown, CT
9.8 463 reviews

Quiet 2 Bed Room Apt W/ Private Entrance.

apartment, Glastonbury
This two-bedroom flat is located in a quiet residential area in South Glastonbury, close to the Connecticut River, hiking trails, shops, and restaurants. The property has received excellent ratings for cleanliness, location, and overall experience.
The accommodation can sleep up to five guests and offers a spacious and comfortable living space. The flat comes equipped with a range of amenities, including a fully-fitted kitchen, a private garden with a patio and barbecue, and a swimming pool.

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

Lovely 3 Bedroom Colonial Home - Middletown, CT
No reviews

Lovely 3 Bedroom Colonial Home

house, Middletown
Accommodation. You will be located in Middletown.
Services and facilities: an iron, a terrace and a washing machine. Take advantage of the Free Parking with this accommodation in Middletown!
3 Br Apartment Near Wesleyan 201 - Middletown, CT
10 2 reviews

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.
3 Br Apartment Near Wesleyan 202 - Middletown, CT
8.0 1 review

3 Br Apartment Near Wesleyan 202

apartment, Middletown
This property is located in Middletown's Washington Street Historic District, a short distance from Wesleyan University and Wadsworth Mansion.
This 93 square metre flat offers accommodation for up to six guests, featuring three bedrooms, a fully equipped kitchen with a dishwasher, and a balcony.
Cabin Deck House - Formidable Cabin In Laurel Island - Middletown, CT
10 2 reviews

Cabin Deck House - Formidable Cabin In Laurel Island

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.

Best pet friendly Middletown, CT holiday rentals

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

#24 *Serenity* A Lakefront Cottage Retreat - Middletown, CT
9.8 25 reviews

#24 *Serenity* A Lakefront Cottage Retreat

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.
Private Apt In Middletown-wesleyan 101 - Middletown, CT
8.9 47 reviews

Private Apt In Middletown-wesleyan 101

apartment, Middletown
This two-bedroom flat is conveniently located in central Middletown, just a short distance from Wesleyan University. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment has a flexible layout with a main level and a loft, accommodating up to four guests. The flat comes equipped with a kitchen, laundry facilities, air conditioning, and a garden, providing everything you need for a comfortable stay.
Fashionably Cozy Place - Middletown, CT
9.4 34 reviews

Fashionably Cozy Place

apartment, Meriden
This apartment is located in Meriden, Connecticut, just a short drive from Hubbard Park, Gouveia Vineyards, and Castle Craig, and is conveniently located 20 minutes from downtown Hartford, 1.5 hours from New York City, and 20 minutes from New Haven. The apartment has received very good user and location ratings, and an excellent cleanliness rating.
This self-catering property has two bedrooms and can accommodate up to four guests. The apartment offers a fully equipped kitchen with a fridge, freezer, and microwave oven, as well as air conditioning, parking, and internet access.
Cozy Cape On Farmington & Plainville Border - Middletown, CT
10 30 reviews

Cozy Cape On Farmington & Plainville Border

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.
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