Middletown holiday rentals: compare the best deals
8.8 3 reviews
Middletown
07/13 – 08/10
HK$2128/nighttotal: HK$59584 (28 )
#28- *Modern Bungalow*
2 3
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.
9.8 136 reviews
Middletown
06/30 – 07/02
HK$1407/nighttotal: HK$2814 (2 )
Perfect Private "Downtown Village" Apartment
1 2
apartment , Middletown
This charming studio apartment is located in a historic district of Middletown, just a block from Wesleyan University and its bustling main street, with a public library across the road. The studio has received excellent user, location, and cleanliness ratings, making it a popular choice for travellers. The studio is spacious and bright, offering comfortable accommodation for two guests. It is fully equipped with a kitchen, washer/dryer, private parking, and a peaceful outdoor space, making it an ideal choice for a relaxing stay in Middletown.
Middletown
07/13 – 08/10
HK$3220/nighttotal: HK$90160 (28 )
Historic Home 3 Miles To Middletown Main Street
6 3
house , Middletown
This historic dwelling in Middletown is situated 3 kilometres from Main Street, 3.4 kilometres from Wesleyan University and 24 kilometres from the Goodspeed Opera House. The property offers 545 square metres of living space with 6 bedrooms, 3 bathrooms, and can accommodate up to 23 guests, featuring a fully equipped kitchen, air conditioning, internet, and private parking.
9.8 338 reviews
Middletown
06/30 – 07/02
HK$1676/nighttotal: HK$3352 (2 )
Historic Greek Revival Brick Home
2 2
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.
Middletown
07/13 – 08/10
HK$4405/nighttotal: HK$123340 (28 )
Carriage House In Higganum Center
1 3
apartment , Haddam
This Higganum Center flat offers central access for exploring Haddam, situated within easy reach of local amenities and community hubs. This four-bedroom flat accommodates up to eight guests and features three and a half bathrooms, a kitchen equipped with a fridge, freezer, microwave, and dishwasher, and air conditioning.
Middletown
06/27 – 07/04
HK$2793/nighttotal: HK$19551 (7 )
Spacious 5-bedroom Family Home
1 2
apartment , New Britain
This New Britain flat is located 35 kilometres from Bradley International Airport. This one-bedroom flat for up to 19 guests offers complimentary WiFi, private parking, and a fully equipped kitchen, with air conditioning and a flat-screen TV provided.
9.3 3 reviews
Middletown
07/13 – 08/10
HK$861/nighttotal: HK$24108 (28 )
(King Bed) Close To Midstate
1 3
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.
10 8 reviews
Middletown
06/30 – 07/02
HK$2458/nighttotal: HK$4916 (2 )
The Farmhouse Loft Guesthouse
1 2
apartment , Middletown
This two-bedroom flat is located in Middletown's historic Highland district, offering rural surroundings just over 1.6 kilometres from downtown and Wesleyan University. This spacious apartment, accommodating up to four guests, features air conditioning, a fully equipped kitchen including a dishwasher, and private parking, with the added bonus of interacting with resident pets Eggnog and Henry.
9.5 8 reviews
Middletown
06/30 – 07/02
HK$2302/nighttotal: HK$4604 (2 )
Lakefront Living
1 2
apartment , Portland
This Portland lakefront apartment is situated near a wooded area, offering easy access to kayaking and swimming. The one-bedroom, one-bathroom apartment sleeps three guests and boasts a private dock, a deck with treetop views, and a jacuzzi, perfect for a relaxing getaway.
10 2 reviews
Middletown
07/13 – 08/10
HK$2199/nighttotal: HK$61572 (28 )
2br Apartment Near Wesleyan 301
2 3
apartment , Middletown
This flat offers a prime location in Middletown's Washington Street Historic District, just 700 metres from Kidcity Children's Museum and a 1.3 kilometre walk to Harbor Park. This 88 square metre accommodation sleeps four guests and features two bedrooms, one bathroom, air conditioning, Wi-Fi, a fully equipped kitchen with a dishwasher, and on-site parking.
8.5 11 reviews
Middletown
07/13 – 08/10
HK$1938/nighttotal: HK$54264 (28 )
Private Apartment In Berlin
1 3
house , Berlin
This two-bedroom house in Berlin, Connecticut is located just 16 kilometres from Wesleyan University and 18 kilometres from the Bushnell Center for Performing Arts, offering easy access to both cultural and educational attractions. The property has received excellent ratings for its cleanliness, location, and overall user experience. The 111 square metre house can comfortably accommodate up to 9 guests and features a fully equipped kitchen, free Wi-Fi, a TV, air conditioning, and a private parking space. Guests can also enjoy a spa and the option to bring their pets along.
Best family friendly Middletown holiday rentals
Among the 100 accommodations in Middletown, here are the 4 best family friendly rentals
9.9 22 reviews
Middletown
06/30 – 07/02
HK$1842/nighttotal: HK$3684 (2 )
Modern 1br Near Wesleyan & Main Street
1 2
apartment , Middletown
This Middletown flat is conveniently located near Main Street's shops and restaurants, a 1.6km stroll from Wesleyan University, and close to Middlesex Hospital, with easy access to Route 9. The newly renovated ground-floor apartment sleeps three, features a full kitchen with dishwasher, in-unit laundry, off-street parking, and air conditioning; enjoy nearby attractions and the comfort of this well-equipped dwelling.
Middletown
06/30 – 07/02
HK$4123/nighttotal: HK$8246 (2 )
Spacious 4-bedroom House On The Water!
4 2
apartment , Meriden
This Meriden house offers a tranquil retreat on Beaver Pond, conveniently located near theme parks and local attractions like Safari Golf. This family-friendly apartment provides four bedrooms, two bathrooms, and accommodation for up to eight guests, featuring a deck overlooking Beaver Pond, a fully equipped kitchen, air conditioning, and proximity to outdoor activities such as kayaking and hiking.
8.7 95 reviews
Middletown
07/13 – 08/10
HK$2095/nighttotal: HK$58660 (28 )
Lovely 3 Bedroom Colonial Home
3 3
house , Middletown
This holiday home is located in Middletown, just 8.5km from Wesleyan University and within easy reach of Central Connecticut State University (17.7km) and the Wadsworth Atheneum (24.1km). It has consistently received excellent ratings for cleanliness, location and user experience. The property offers 127 square metres of space, comfortably accommodating up to 6 guests in 3 bedrooms and 2 bathrooms. Guests can enjoy a peaceful garden, a balcony, a fully equipped kitchen, laundry facilities, streaming services, free parking and Wi-Fi.
9.8 27 reviews
Middletown
06/30 – 07/02
HK$7349/nighttotal: HK$14698 (2 )
New Modern, Luxurious Home On 2.5 Acres. 10 Min To Powder Ridge & Middletown.
4 2
apartment , Durham
This Durham holiday home is situated approximately 2.3 kilometres from Millers Pond State Park, and within 10 kilometres of Ron McCutcheon Park and Tri-Mountain State Park, offering easy access to local recreational areas and Lyman Orchards. The four-bedroom property sleeps eight guests, boasting three bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, a terrace, garden, parking, and free Wi-Fi; enjoy a comfortable stay with amenities such as a fireplace and barbecue facilities.
Best Middletown holiday rentals with parking
10 4 reviews
Middletown
06/30 – 07/02
HK$1165/nighttotal: HK$2330 (2 )
Sunny Private 1 Bedroom Apartment
1 2
apartment , Portland
This Portland flat offers a convenient 5-10 minute drive to Wesleyan University, Downtown Middletown for amenities, Middlesex Hospital, and Saint Clements Castle. This one-bedroom, one-bathroom flat accommodates up to three guests and features air conditioning, Wi-Fi, a kitchen with a fridge and microwave, and parking, with a reading nook/office space.
8.0 61 reviews
Middletown
06/30 – 07/02
HK$2188/nighttotal: HK$4376 (2 )
Two Families, Up And Down Stairs, The 2nd Floor Is The Vrbos Apartment
3 2
apartment , New Britain
This New Britain apartment is situated in a peaceful and safe neighbourhood, just a short distance from Central Connecticut State University (CCSU) and local amenities. The apartment has received very good ratings for location, cleanliness and overall user experience. The property has three bedrooms and a bathroom, along with a living area, full kitchen and dining room. It includes amenities such as air conditioning, parking, internet and a microwave.
9.8 23 reviews
Middletown
06/30 – 07/02
HK$2717/nighttotal: HK$5434 (2 )
#24 *Serenity* A Lakefront Cottage Retreat
2 2
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.
9.8 15 reviews
Middletown
06/30 – 07/02
HK$5759/nighttotal: HK$11518 (2 )
Home Away From Home Hot Tub And Pool In Middletown Home Of Wesleyan University
3 2
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
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 and September to October. The weather is still pleasant during these months, but the crowds are smaller and the prices are lower.
What are the best Airbnb and vacation rentals in Middletown?
What events or festivals should visitors check out in and around Middletown, CT?
Middletown hosts a variety of events throughout the year. The Middletown Arts Festival is a popular event in the summer, showcasing local artists and musicians. In the autumn, the Middletown Fall Festival features a parade, live music, and a craft fair. And if you're in town during the winter, be sure to check out the Middletown Holiday Festival, which features a tree lighting ceremony, carols, and Santa Claus.
What are the best budget-friendly activities in Middletown, CT?
Middletown has plenty of free and budget-friendly activities to offer. You can take a walk or bike ride along the scenic Connecticut River, visit the free exhibits at the Wesleyan University Art Museum, or explore the historic downtown area.
What are the best vacation rentals with a pool in Middletown?
What are the best restaurants with local dishes in Middletown, CT?
For a taste of Middletown's local cuisine, you should definitely check out the Silver Star Restaurant. They're known for their classic American dishes, including their famous burgers and fries. If you're looking for something a bit more upscale, the A Mano Restaurant is a great choice, with its focus on fresh, seasonal ingredients.
What are the best rentals for families and kids in Middletown?
What are the best walking or cycling routes in Middletown, CT?
The Mattabesett Trail is a popular walking and cycling route that runs through Middletown. It's a scenic trail that follows the Mattabesett River and offers beautiful views of the surrounding countryside. For a shorter, more urban walk, you can explore the downtown area and its historic streets.
What are the best rentals or Airbnbs with a jacuzzi in Middletown?
Are there pet-friendly attractions in Middletown, CT?
Many of Middletown's parks and gardens are pet-friendly. The Wadsworth Mansion allows well-behaved dogs on leashes in its gardens, and the Long Hill Estate and Gardens also welcomes furry friends. You can also find pet-friendly restaurants and cafes in the downtown area.
What are the benefits of choosing a vacation rental in Middletown, CT?
Vacation rentals in Middletown offer more space and privacy than hotels, often at a lower cost. They also provide access to kitchens and laundry facilities, which can be convenient for families or longer stays. You might also enjoy the unique character and charm of a home away from home.
What are the top sports attractions and facilities in Middletown, CT?
Middletown is home to several sports facilities, including the Wesleyan University athletic fields and the Middletown YMCA. The city also hosts a variety of sporting events, including high school football games and the annual Middletown Marathon.
Destinations nearby
Best Middletown holiday rentals with a balcony
Middletown
06/30 – 07/02
HK$2619/nighttotal: HK$5238 (2 )
3 Br Apartment Near Wesleyan 201
3 2
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.
8.2 10 reviews
Middletown
07/13 – 08/10
HK$1568/nighttotal: HK$43904 (28 )
Fashionably Cozy Place
2 3
apartment , Meriden
This two-bedroom apartment is situated in Meriden, conveniently located 16 km from Wesleyan University, 22 km from Lake Compounce, and 22 km from Central Connecticut State University. The surrounding area is peaceful and offers easy access to attractions, making it a great base for exploring the region. This property has received excellent ratings for cleanliness and location, ensuring a comfortable and enjoyable stay. The 121 square metre apartment comfortably sleeps six guests and features a fully equipped kitchen with a fridge and microwave, as well as air conditioning, free Wi-Fi, and parking. It is ideal for families or groups looking for a self-contained accommodation with a range of amenities, and is perfect for exploring Meriden and its surroundings.
Middletown
06/30 – 07/02
HK$3032/nighttotal: HK$6064 (2 )
3 Br Apartment Near Wesleyan 202
3 2
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.
10 2 reviews
Middletown
06/27 – 07/04
HK$3883/nighttotal: HK$27181 (7 )
Cabin Deck House - Formidable Cabin In Laurel Island
4 2
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 holiday rentals
Among the 100 accommodations in Middletown, here are the 4 best pet friendly rentals
Middletown
07/13 – 08/10
HK$4578/nighttotal: HK$128184 (28 )
Finca Spadola
1 3
apartment , Durham
Finca Spadola, a four-bedroom property sleeping eight, is situated in rural Durham, its precise location unspecified but likely a short drive from the city centre and County Durham's historical attractions. This restored 1900s farmhouse boasts a 3-acre site with extensive outdoor entertaining areas including covered patios, multiple fire pits, a pizza oven, outdoor bar, and Weber grills; indoor amenities include a fully equipped kitchen, 85” smart TV, and games like horseshoes and cornhole are provided.
9.0 1 review
Middletown
07/13 – 08/10
HK$1879/nighttotal: HK$52612 (28 )
Apartment In Middletown-wesleyan 301
1 3
apartment , Middletown
This Middletown-Wesleyan 301 flat is situated in Middletown, a mere 550 metres from Wesleyan University, and 21 kilometres from Central Connecticut State University. This residence offers 88 square metres of living space with two bedrooms, a fully equipped kitchen, and capacity for six guests, complete with complimentary on-site parking and Wi-Fi.
Middletown
07/13 – 08/10
HK$1873/nighttotal: HK$52444 (28 )
Apartment In Middletown-wesleyan102
1 3
apartment , Middletown
This Middletown flat offers a prime location, a mere 640-metre walk from Wesleyan University and within 24 kilometres of Central Connecticut State University, Trinity College, and Goodspeed Opera House. This 88 square metre apartment accommodates up to five guests with two bedrooms, one bathroom, air conditioning, and on-site parking, boasting a fully equipped kitchen with a fridge and microwave, plus free Wi-Fi.
9.9 75 reviews
Middletown
06/30 – 07/02
HK$1099/nighttotal: HK$2198 (2 )
Rv/camper Farm Stay
1 2
gîte , Portland
This charming gîte is situated in a peaceful rural setting near Portland, Connecticut, just a short drive from Middletown and Glastonbury. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The renovated 1961 Shasta camper comfortably accommodates up to four guests and features a full kitchenette, a bathroom with a shower, and a Keurig coffee maker. Guests can enjoy the tranquility of a working farm, participate in farm chores, and explore the surrounding historical structures.