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

1r Private Downtown Oasis

apartment, Middletown
This charming apartment is located in downtown Middletown, just a block from Wesleyan University and Main Street, with the public library across the street. It has consistently received excellent ratings for location, cleanliness, and user experience.
The apartment offers a comfortable stay for up to 4 guests, featuring a private bedroom and a fully equipped kitchen. Amenities include a fenced-in backyard with a stone patio, private parking, a washer/dryer, and modern conveniences like Wi-Fi and air conditioning.
2r Sunny Private "Downtown Village" Apartment - Middletown, CT
9.7 138 reviews

2r Sunny Private "Downtown Village" Apartment

apartment, Middletown
This studio apartment is located in a historic district of Middletown, just one block from Wesleyan University and the main street with restaurants and coffee shops. The studio has received excellent ratings for its location, cleanliness, and overall experience.
This charming apartment can comfortably accommodate two guests and features a fully equipped kitchen, a private bathroom, and a washer and dryer for added convenience. Enjoy the peaceful retreat of the fenced-in rear yard, and take advantage of amenities like a TV, wireless internet, and a private parking space.
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.

Best Middletown, CT vacation rentals with air conditioning

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 basement apartment is located in a quiet residential neighborhood in South Glastonbury, close to the Connecticut River and within easy reach of hiking trails, shops, and restaurants. It boasts excellent user, location, and cleanliness ratings.
This two-bedroom, one-bathroom rental can comfortably accommodate up to five guests. The apartment features a fully equipped kitchen, air conditioning, a private garden, and a swimming pool (currently under reconstruction).
Modern 1br Near Wesleyan & Main Street - Middletown, CT
9.9 29 reviews

Modern 1br Near Wesleyan & Main Street

apartment, Middletown
This Middletown apartment rental is conveniently located near Main Street, a mile from Wesleyan University, and close to Middlesex Hospital, offering easy access to Route 9.
The newly renovated one-bedroom unit sleeps three guests and features a full kitchen with dishwasher, in-unit laundry, air conditioning, and off-street parking.
#29 - Modern 5 Bedroom/2 Bath - Middletown, CT
9.4 66 reviews

#29 - Modern 5 Bedroom/2 Bath

apartment, Middletown
This accommodation is located in Middletown, a city with a rich history and a charming downtown area. It offers 5 bedrooms and 2 bathrooms, making it suitable for up to 10 guests.
The accommodation is fully equipped with modern amenities to ensure a comfortable stay. Guests can enjoy a variety of activities in the surrounding area, including hiking, biking, and fishing. The accommodation is also close to several restaurants, shops, and cultural attractions.
Seasons Hospitality 1br With Private Deck C3 - Middletown, CT
9.6 40 reviews

Seasons Hospitality 1br With Private Deck C3

apartment, Wallingford
This Wallingford apartment is conveniently located near Yale University, Wesleyan University, and the Yale Bowl, making it a great choice for travelers visiting these institutions. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to two guests. Enjoy amenities like air conditioning, free parking, a fully equipped kitchen, and a garden, perfect for relaxing after a day of exploring Wallingford's scenic parks and hiking trails.

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.

#29 - Modern 5 Bedroom/2 Bath - Middletown, CT
9.4 6 reviews

#29 - Modern 5 Bedroom/2 Bath

apartment, Middletown
This stylish 5-bedroom apartment is located in a private neighborhood in Middletown, Connecticut, minutes away from Wadsworth Falls State Park, Dinosaur State Park, and Wesleyan University. It has an excellent user rating.
The apartment offers a spacious layout with 1700 square feet of floor area and can accommodate up to 10 guests. It features modern amenities such as herringbone flooring, high-speed internet, smart TVs, a fully equipped kitchen, comfortable bedding, and entertainment options. Guests staying 3+ months have exclusive garage access.
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.
3 Br Apartment Near Wesleyan 201 - Middletown, CT
10 1 review

3 Br Apartment Near Wesleyan 201

apartment, Middletown
This 3-bedroom apartment in Middletown is an 8-minute walk from Wesleyan University and 28 miles from Tweed-New Haven Airport.
This 950 square foot dwelling accommodates up to 8 guests with a full kitchen, air conditioning, free Wi-Fi, and on-site parking.
3 Br Apartment Near Wesleyan 202 - Middletown, CT
No reviews

3 Br Apartment Near Wesleyan 202

apartment, Middletown
This 1000 sq ft, 3-bedroom apartment is located near Wesleyan University in Middletown, offering 1 bathroom and accommodating up to 8 guests.
This rental includes air conditioning, a full kitchen with a dishwasher and oven, complimentary on-site parking, and free high-speed WiFi.

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.

Belltown House At Airline Trail - Middletown, CT
No reviews

Belltown House At Airline Trail

apartment, East Hampton
This East Hampton vacation home offers a countryside and waterfront location, 2 minutes from Lake Pocotopaug and 6 minutes from Day Pond State Park.
This 930 sq ft, 3-bedroom, 1-bathroom house accommodates up to 6 guests and features a fully equipped kitchen, on-site parking, and proximity to powerboating and the riverbank.
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.
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.
Lake Me Home - Middletown, CT
9.0 2 reviews

Lake Me Home

house, East Hampton
Lake Me Home, a beachfront property in East Hampton, is located 11 miles from Wesleyan University and the Goodspeed Opera House, and 30 miles from Bradley International Airport, offering direct beach access.
This 7,360-square-foot East Hampton home sleeps nine guests and features a fully equipped kitchen, private parking, Wi-Fi, a sun terrace, outdoor fireplace, and washer/dryer, with nearby fishing and hiking opportunities.

Best Middletown, CT vacation rentals with parking

Seasons Hospitality Offers All New 1br With Tons Of Charm - Middletown, CT
10 1 review

Seasons Hospitality Offers All New 1br With Tons Of Charm

apartment, Wallingford
Hilltop A-frame Retreat - Middletown, CT
9.5 4 reviews

Hilltop A-frame Retreat

apartment, Middletown
Charming 1br Retreat | Free Parking + Wifi C5 - Middletown, CT
9.8 46 reviews

Charming 1br Retreat | Free Parking + Wifi C5

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

Historic Home 3 Mi To Middletown Main Street

cottage, Middletown

Compare Luxury Vacation Rentals in Middletown, CT

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

Middletown Ct Private Apt  - Walk To Wesleyan U - Middletown, CT
10 103 reviews

Middletown Ct Private Apt - Walk To Wesleyan U

apartment, Middletown

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.

Renovated Apt - 4min Walk From Wesleyan & Main St - Middletown, CT
9.2 42 reviews

Renovated Apt - 4min Walk From Wesleyan & Main St

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

Private Apartment In Berlin

apartment, Berlin
The Studio Apartment - Middletown, CT
9.7 36 reviews

The Studio Apartment

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

3 Br Apartment Near Wesleyan 202

apartment, Middletown

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.

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

Quiet 2 Bed Room Apt W/ Private Entrance.

apartment, Glastonbury

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.

Brownstone Oasis - Middletown, CT
9.8 10 reviews

Brownstone Oasis

apartment, Portland
The Studio Apartment - Middletown, CT
9.7 36 reviews

The Studio Apartment

apartment, Meriden
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