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Middletown, CT vacation rentals
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Best Vacation rentals and Airbnb offers in Middletown, CT

Search Vacation Rentals near the Old Town in Middletown, CT

These central Middletown, CT vacation rentals make exploring downtown easy on foot. Skip the hassle of transfers and enjoy a convenient city stay.

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

Private Apt In Middletown-wesleyan 101

apartment, Middletown
This 2-bedroom, 1-bathroom rental unit is located in central Middletown, just a short walk from Wesleyan University, offering convenient access to local restaurants and shops.
This pet-friendly apartment accommodates up to 5 guests and features a full kitchen, in-unit laundry, air conditioning, and parking, making it suitable for short or extended stays.
2br Apartment Near Wesleyan 301 - Middletown, CT
10 3 reviews

2br Apartment Near Wesleyan 301

apartment, Middletown
This Washington Street Historic District apartment in Middletown offers on-site parking and is located 0.75 miles from Harbor Park and 0.38 miles from Kidcity Children's Museum.
This 950 sq ft dwelling accommodates up to 4 guests with 2 bedrooms, 1 bathroom, and features air conditioning, Wi-Fi, a full kitchen, and an in-unit washer and dryer.
2br Apartment Near Wesleyan 301 - Middletown, CT
8.8 8 reviews

2br Apartment Near Wesleyan 301

apartment, Middletown
This two-bedroom, one-bathroom rental unit is located in Middletown, a short distance from Wesleyan University.
This pet-friendly apartment offers on-site parking, a fully equipped kitchen with a fridge, microwave, and dishwasher, and accommodates up to four guests.
Private Apt In Middletown-wesleyan 101 - Middletown, CT
8.9 47 reviews

Private Apt In Middletown-wesleyan 101

apartment, Middletown
This apartment is located in Middletown, just a short distance from Wesleyan University, making it a convenient choice for visitors attending events or visiting students. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers a comfortable and spacious living space, perfect for accommodating up to 4 guests. The apartment is equipped with modern amenities, including a fully equipped kitchen, in-unit laundry, and a versatile loft space with a queen bed and a convertible couch.

Best Middletown, CT vacation rentals with air conditioning

Brownstone Oasis - Middletown, CT
9.8 10 reviews

Brownstone Oasis

apartment, Portland
This two-bedroom, one-bathroom rental unit is located in a central Portland district, offering convenient access to prominent landmarks and attractions such as Powell's City of Books, approximately 1,500 feet away, and Pioneer Courthouse Square, just under 1 mile away.
This stylish apartment accommodates up to eight guests and includes amenities such as internet, air conditioning, a kitchen, a jacuzzi, and parking, making it a comfortable retreat for exploring Portland.
Delightful And Cozy Home In Middletown - Middletown, CT
9.3 128 reviews

Delightful And Cozy Home In Middletown

house, Middletown
This house is conveniently located in Middletown, just a short distance from major landmarks and attractions. It has received excellent ratings for location, cleanliness, and overall user experience. This home provides a comfortable and convenient stay for travelers. It features a well-equipped kitchen with a fridge, air conditioning, a garden, and parking. You can enjoy the outdoors or relax inside with access to the internet and a comfortable living space.
Private Apartment  In Berlin - Middletown, CT
9.0 7 reviews

Private Apartment In Berlin

apartment, Berlin
This Berlin, Maryland vacation home is conveniently located 1.8 miles from New Britain Stadium and 2.5 miles from Putter's Paradise Mini Golf, a 13-minute walk from Berlin Station.
This 1190-square-foot house sleeps four, offering two bedrooms, one bathroom, a fully equipped kitchen with dishwasher, in-house laundry, free WiFi, a Smart TV, air conditioning, parking, and a children's playground.
3 Br Apartment Near Wesleyan 201 - Middletown, CT
8.7 9 reviews

3 Br Apartment Near Wesleyan 201

apartment, Middletown
This second-floor apartment in Middletown is located a stone's throw from Wesleyan University, offering convenient access to the campus and surrounding area.
This pet-friendly residence accommodates up to six guests with three bedrooms, one bathroom, and a fully equipped kitchen, featuring a porch and on-site laundry for added convenience.

Frequently Asked Questions about vacation rentals in Middletown, CT

  • Which neighborhood in Middletown, CT should you consider for a vacation rental?

    The area around the Wesleyan University campus is a good choice, as it's close to downtown and has a lot of restaurants and shops. If you're looking for something quieter, the neighborhoods around Harbor Park and the Connecticut River are nice options.
  • 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 Apartment Near Wesleyan - Downtown - Wedding Venues 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?

    It depends on what you're looking for! If you want to avoid the crowds, the shoulder seasons of spring and fall are great. Summer is the busiest time, but also when there are the most festivals and events. And if you're looking for a winter getaway, Middletown has a charming holiday atmosphere.
  • What are the most popular Airbnbs in Middletown, CT?

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

    The Mattabesett Trail is a great place to hike or bike for free, and the Middletown Public Library has a ton of free programs and events. You can also walk or bike along the Connecticut River for some beautiful views.
  • What are the best vacation rentals with a pool in Middletown, CT?

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

    The Black Sheep is a popular spot for local fare, and they have a great selection of craft beers. For something a little more upscale, try the restaurant at the Wadsworth Mansion, which features seasonal menus with local ingredients. And if you're looking for a casual bite, the Main Street Cafe is a great option.
  • What are the best rentals for families and kids in Middletown, CT?

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

    The Mattabesett Trail is a great option for both walking and cycling, and it runs for miles along the Connecticut River. You can also walk or bike around the Wesleyan University campus, which has beautiful grounds and a lot of interesting architecture.
  • What are the best rentals or Airbnbs with a jacuzzi in Middletown, CT?

    The best vacation rentals or Airbnb with a jacuzzi in Middletown, CT are A Luxury Estate Elegant & Private~white Lion Manor, Lovely 3 Bedroom Colonial Home and Newly Remodeled Entire Apartment & Loft.

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

    Yes, the Mattabesett Trail is a great place to walk your dog, and there are a number of dog-friendly restaurants and cafes in downtown Middletown. The Connecticut River Museum also welcomes leashed dogs on their grounds.
  • What are the benefits of choosing a vacation rental in Middletown, CT?

    Vacation rentals offer more space and privacy than hotels, and they can be a great option for families or groups. They also often come with amenities like kitchens and laundry facilities, which can save you money on meals and laundry.
  • What are the top sports attractions and facilities in Middletown, CT?

    Middletown has a number of sports facilities, including the Wesleyan University athletic complex, which has a track, tennis courts, and a baseball field. The city also has a number of parks with basketball courts, playgrounds, and other recreational facilities.

Popular destinations

Best Vacation Rentals with Balconies in Middletown, CT

Wake up to breathtaking views at these Middletown, CT vacation rentals with balconies, perfect for your morning coffee.

Cabin Deck House - Formidable Cabin In Laurel Island - Middletown, CT
10 2 reviews

Cabin Deck House - Formidable Cabin In Laurel Island

cabin, East Hampton
This charming cabin is located in Laurel Island, just a short drive from East Hampton and its beaches, as well as Wesleyan University and Goodspeed Opera House. The cabin consistently receives excellent reviews for its cleanliness, location, and overall experience.
The cabin offers four bedrooms, making it perfect for families or groups of friends. Enjoy the private terrace, garden, and lake views, or prepare meals in the fully equipped kitchen with a fridge and freezer.
Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger - Middletown, CT
9.6 13 reviews

Lake Front Home, Dock W/2 Kayaks, Firepit, Grill, Pedal Boat. Lv2 Ev Charger

apartment, Haddam
This waterfront vacation home in Killingworth is located near Cockaponset State Forest and Sundial Herb Garden, offering easy access to scenic hiking trails and unique botanical attractions. It has earned excellent user ratings, making it a popular choice for travelers.
This 1300 square foot house comfortably sleeps up to 10 guests in its 4 bedrooms and 1 bathroom. Enjoy the convenience of a fully equipped kitchen, air conditioning, a private terrace, a garden, and parking, perfect for relaxing and exploring the surrounding area.
Convenient, Cozy Home: Porches, Fire Pit, Office - Middletown, CT
No reviews

Convenient, Cozy Home: Porches, Fire Pit, Office

house, Meriden
This Meriden vacation rental is located 7.5 miles from Wesleyan University and 22 miles from Tweed-New Haven Airport, with Lake Compounce and Yale University also accessible.
This 1820 sq ft house features 3 bedrooms, 4 bathrooms, a full kitchen, garden, terrace, and fitness center, accommodating up to 15 guests.
Quarry House: Mid-century Modern - Middletown, CT
9.0 2 reviews

Quarry House: Mid-century Modern

apartment, Haddam
This Haddam, Connecticut home, known as the Quarry House, sits atop a hill near the Connecticut River, offering easy access to attractions like the Goodspeed Opera House and the East Haddam Historical Society Museum.
The 2170-square-foot mid-century modern residence boasts four bedrooms, three bathrooms, and accommodates eight guests, featuring a fully equipped kitchen, air conditioning, a terrace, a garden, parking, and proximity to the Sundial Herb Garden and Kidcity Children's Museum.

Neighborhoods and points of interest in Middletown, CT

Top Vacation Rentals for Families in Middletown, CT

These kid-friendly vacation rentals in Middletown, CT keep you close to top city attractions for a stress-free family vacation.

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 vacation home, near Gouveia Winery (2.6 miles) and Paradise Hills Vineyard (within 6 miles), offers a peaceful rural setting close to Tradition Golf Club and other attractions.
This 1610-square-foot house features three bedrooms, three bathrooms, sleeps ten guests, and includes amenities such as a fully equipped kitchen, Wi-Fi, a terrace, a spa, and parking.
New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown. - Middletown, CT
10 31 reviews

New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown.

apartment, Durham
This Durham vacation home is conveniently located near Millers Pond State Park (1.4 miles) and within 6 miles of Ron McCutcheon Park, Tri-Mountain State Park, Lyman Orchards, and Lyman Meadow Golf Club.
This spacious four-bedroom house, sleeping up to eight guests, features a fully equipped kitchen, a fireplace, barbecue grills, and a terrace—perfect for families seeking outdoor recreation near Durham's parks and orchards.
Clean, Bright & Private Whole House 4 You. Safe, Centrally Located, Garage - Middletown, CT
10 16 reviews

Clean, Bright & Private Whole House 4 You. Safe, Centrally Located, Garage

apartment, New Britain
This New Britain vacation home offers easy access to the New Britain Museum of American Art (6-minute drive) and New Britain Stadium (4-minute drive), plus convenient proximity to Silver Lake State Access Area and the Connecticut River.
This three-bedroom, one-bathroom house sleeps eight guests and includes air conditioning, laundry facilities, and essential amenities; nearby attractions include Putter's Paradise Mini Golf, Callahan's Bowl-a-Rama, and Crystal Bees Bowling.
Fashionably Cozy Place - Middletown, CT
No reviews

Fashionably Cozy Place

apartment, Meriden
Accommodation. You will be based in Meriden.
Services and facilities include an iron, free parking and a washing machine. Take advantage of the air conditioning in this apartment in Meriden.

Best Middletown, CT vacation rentals with parking

3 Br Apartment Near Wesleyan 201 - Middletown, CT
10 2 reviews

3 Br Apartment Near Wesleyan 201

apartment, Middletown
Historic Home 3 Mi To Middletown Main Street - Middletown, CT
No reviews

Historic Home 3 Mi To Middletown Main Street

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

3 Br Apartment Near Wesleyan 202

apartment, Middletown

Compare Luxury Vacation Rentals in Middletown, CT

Discover high-end comfort in Middletown, CT with upscale rentals that prioritize luxury and guest satisfaction.

New England Getaway - Middletown, CT
9.6 47 reviews

New England Getaway

apartment, Berlin

Our Favorite Pet-Friendly Vacation Rentals in Middletown, CT

Experience a pet-friendly stay in Middletown, CT with vacation rentals located steps away from city dog parks and walking trails.

Ct River Retreat - Modern Home With Ct River Views - Middletown, CT
10 60 reviews

Ct River Retreat - Modern Home With Ct River Views

house, East Hampton

Explore Vacation Rentals with a Pool in Middletown, CT

Choose a vacation rental in Middletown, CT with a swimming pool for a proper workout or a leisurely dip right in the heart of the city.

Hot Tub And Pool Home Away From Home - Middletown, CT
9.9 57 reviews

Hot Tub And Pool Home Away From Home

house, Middletown
Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University - Middletown, CT
9.6 19 reviews

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

apartment, Middletown

Search Vacation Rentals with Jacuzzi in Middletown, CT

Unwind at the end of a busy city day with a private hot tub at these hand-selected vacation rentals in Middletown, CT.

Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University - Middletown, CT
9.6 19 reviews

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

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

Brownstone Oasis

apartment, Portland
Hot Tub And Pool Home Away From Home - Middletown, CT
9.9 57 reviews

Hot Tub And Pool Home Away From Home

house, Middletown
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