This A-frame lodge, offering exceptional privacy, is situated on a hilltop overlooking Highland Pond and a 32-acre nature preserve, a short distance from Middletown's attractions. This spacious two-level property, covering over 185 square meters, accommodates up to four guests with two en-suite bedrooms, a gourmet kitchen, a dedicated yoga room, and an expansive deck for enjoying the panoramic views.
Middletown, CT
13/07 – 10/08
NZ$967/nighttotal: NZ$27076 (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, CT
13/07 – 10/08
NZ$1710/nighttotal: NZ$47880 (28 )
Conference Room Rental No Sleeping Arrangements
1 3
apartment , Cromwell
This Cromwell apartment is situated less than 1.6km from the Connecticut River and its State Wildlife Area, and within 4.8km of River Highlands State Park and the TPC River Highlands golf course. The one-bedroom flat offers a sofa bed, sleeping up to 30 guests, free Wi-Fi, air conditioning, and is close to hiking trails and scenic river walks.
Middletown, CT
13/07 – 10/08
NZ$661/nighttotal: NZ$18508 (28 )
3 Br Apartment Near Wesleyan 202
3 3
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.
Middletown, CT
13/07 – 10/08
NZ$947/nighttotal: NZ$26516 (28 )
Sunny Garden Home
1 3
apartment , Meriden
This Meriden flat is located in a quiet, family-friendly district, offering a peaceful retreat from the city's bustle. This two-bathroom flat accommodates four guests and features a kitchen, air conditioning, and garden access, providing a comfortable base for exploring local amenities.
9.8 4 reviews
Middletown, CT
13/07 – 10/08
NZ$265/nighttotal: NZ$7420 (28 )
Chic With Recliner At Webster Hill Suite 1w Request Xtra Bed
1 2
apartment , New Britain
Webster Hill Suites, situated in New Britain, Connecticut, is 4.2 km from Central Connecticut State University and within a 16-20 km radius of attractions including the Mark Twain House & Museum, Elizabeth Park, Trinity College, Lake Compounce, the Bushnell Center for the Performing Arts, and the XL Center. This one-bedroom apartment, offering 59 square metres of space, sleeps four guests and features a fully equipped kitchen, outdoor seating, and amenities such as towels, bed linen, and air conditioning; bicycle rentals and opportunities for skiing and fishing are nearby.
Middletown, CT
08/07 – 09/07
NZ$626/nightfor 1 night
Cozy Family Home-sleeps 6 Near Wesleyan & Weddings
1 4
apartment , Middletown
This apartment is located in a secluded cul-de-sac in Middletown, offering privacy and easy access within 500 meters to Main Street's shops and eateries, Wesleyan University, and local wedding venues. This accommodation sleeps six and features two newly renovated bathrooms, a dining area for six, an eat-in kitchen, and a spacious backyard, with flexible sleeping arrangements including two queen beds, a twin bed, a futon, and a daybed.
Middletown, CT
27/06 – 04/07
NZ$589/nighttotal: NZ$4123 (7 )
Windshire Terrace Apartments
1 2
apartment , Middletown
This one-bedroom apartment is conveniently located in Middletown, Connecticut, within easy walking distance of the town centre, offering easy access to shops, restaurants and entertainment venues. The apartment boasts a spacious open-plan living area, a working gas fireplace, a sunny picnic area and a resort-style swimming pool and fitness centre on-site.
9.0 7 reviews
Middletown, CT
13/07 – 10/08
NZ$408/nighttotal: NZ$11424 (28 )
Private Apartment In Berlin
2 2
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.
9.5 103 reviews
Middletown, CT
08/07 – 09/07
NZ$468/nightfor 1 night
59 Old Maids Lane Pool House
1 4
house , Glastonbury
This unique tiny house is situated on Old Maids Lane in Glastonbury, just a short distance from the Connecticut River and hiking trails, offering a peaceful and tranquil setting. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. The two-storey tiny house sleeps up to four guests and features a well-equipped kitchen, a combined washer/dryer, and a private bathroom. Guests can enjoy the shared pool, a stone patio, and a pergola, making it ideal for relaxing and enjoying the outdoors.
9.3 9 reviews
Middletown, CT
13/07 – 10/08
NZ$190/nighttotal: NZ$5320 (28 )
Quaint Studio Walkable To Downtown And Wesleyan
1 2
apartment , Middletown
This Middletown studio apartment is conveniently located 0.8km from Wesleyan University and 1.6km from Middletown's city centre. The self-contained unit, sleeping two, features a kitchenette with hotplate, microwave, fridge and kettle, a private shower room, and a double bed; guests can easily explore downtown Middletown's restaurants and shops.
Middletown, CT
13/07 – 10/08
NZ$556/nighttotal: NZ$15568 (28 )
3 Br Apartment Near Wesleyan 202
1 2
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.
Best family friendly Middletown, CT holiday rentals
Among the 100 accommodations in Middletown, CT, here are the 4 best family friendly rentals
8.0 59 reviews
Middletown, CT
13/07 – 10/08
NZ$313/nighttotal: NZ$8764 (28 )
Two Families, Up And Down Stairs, The 2nd Floor Is The Vrbos Apartment
3 3
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.
8.0 7 reviews
Middletown, CT
13/07 – 10/08
NZ$350/nighttotal: NZ$9800 (28 )
Spacious And Quiet
3 3
apartment , Meriden
This three-bedroom Meriden apartment, ideal for families or groups of up to six, is conveniently located within a 2.4km walk of MidState Medical Center and Westfield Meriden shopping centre, and within 3.2km of Cedar Park and Falcon Field. The self-catering flat offers free on-site parking, free Wi-Fi, a Smart TV, a fully equipped kitchen including oven, hob, microwave, fridge and coffee maker, and is situated in a smoke-free building.
9.7 254 reviews
Middletown, CT
08/07 – 09/07
NZ$609/nightfor 1 night
Beautiful Sunny Apartment In Historic Village
1 4
apartment , Middletown
This charming apartment is located in Middletown's Downtown Village Historic District, just a short walk from Wesleyan University and the public library. The property has excellent user, location, and cleanliness ratings. The apartment is situated on the second floor of a beautifully preserved 1849 Greek Revival brick home and can comfortably accommodate up to six guests. Guests can enjoy a fully equipped kitchen, a relaxing living room with cable TV and Wi-Fi, and access to a private garden.
8.8 94 reviews
Middletown, CT
13/07 – 10/08
NZ$453/nighttotal: NZ$12684 (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.
Best Middletown, CT holiday rentals with parking
Middletown, CT
13/07 – 10/08
NZ$511/nighttotal: NZ$14308 (28 )
Simple Comfort And Tranquility
1 2
apartment , New Britain
This New Britain flat is a 15-minute walk from the New Britain Museum of American Art and a 7-minute walk from Walnut Hill Park, offering convenient access to city attractions. This apartment features air conditioning, Wi-Fi, a fully equipped kitchen with an oven and fridge, and on-site covered garage parking, with nearby attractions including Winding Trails Recreation and Nature Association and Dinosaur State Park.
Middletown, CT
13/07 – 10/08
NZ$240/nighttotal: NZ$6720 (28 )
Chic Suite With Recliner - Webster Hill Suite 1w
1 2
apartment , New Britain
This New Britain flat offers convenient access to local attractions, being a 15-minute walk from the New Britain Museum of American Art and a 7-minute walk from Walnut Hill Park. This residence features air conditioning, Wi-Fi, a kitchen equipped with a fridge and microwave, and a covered garage, with laundry services also available.
Middletown, CT
08/07 – 09/07
NZ$591/nightfor 1 night
3 Br Apartment Near Wesleyan 201
1 4
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.
9.0 1 review
Middletown, CT
13/07 – 10/08
NZ$420/nighttotal: NZ$11760 (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.
Frequently asked questions about holiday rentals in Middletown, CT
When is the best time to book a vacation rental in Middletown, CT?
You'll want to book well in advance if you're planning to visit during the summer months, especially if you're looking for a specific property. The peak season runs from June to August, so you'll get the best selection if you book early.
What are the best Airbnb and holiday rentals in Middletown, CT?
What are the best walking or cycling routes in Middletown, CT?
The Mattabesett Trail is a great option for a walk or bike ride, it runs along the Connecticut River and offers beautiful views of the surrounding area. The Air Line Trail is another good choice, it's a paved path that's perfect for a leisurely ride.
What are the most popular Airbnbs in Middletown, CT?
Are there pet-friendly attractions in Middletown, CT?
Many of the parks in Middletown are pet-friendly, including the Harbor Park and the Wickham Park. The Connecticut River Museum also welcomes well-behaved dogs on a leash.
What are the best holiday rentals with a pool in Middletown, CT?
Best Middletown, CT holiday rentals with a balcony
8.2 10 reviews
Middletown, CT
13/07 – 10/08
NZ$344/nighttotal: NZ$9632 (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.
10 2 reviews
Middletown, CT
27/06 – 04/07
NZ$852/nighttotal: NZ$5964 (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.
8.8 3 reviews
Middletown, CT
13/07 – 10/08
NZ$467/nighttotal: NZ$13076 (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.
Middletown, CT
08/07 – 09/07
NZ$776/nightfor 1 night
3 Br Apartment Near Wesleyan 201
3 4
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.
Best pet friendly Middletown, CT holiday rentals
Among the 100 accommodations in Middletown, CT, here are the 4 best pet friendly rentals
9.1 29 reviews
Middletown, CT
13/07 – 10/08
NZ$325/nighttotal: NZ$9100 (28 )
Private Apartment In Berlin
1 3
house , Berlin
This charming townhome is located in Berlin, Connecticut, a short drive from the town centre and within easy reach of the scenic Farmington River. The property is situated in a peaceful neighbourhood, close to local shops and restaurants. The house has two bedrooms, each with a queen-sized bed, accommodating up to five guests. The well-equipped kitchen features modern appliances, a spacious backyard provides a comfortable outdoor space for enjoying meals, and a private driveway offers convenient parking.
Middletown, CT
27/06 – 04/07
NZ$613/nighttotal: NZ$4291 (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.
9.8 453 reviews
Middletown, CT
08/07 – 09/07
NZ$425/nightfor 1 night
Quiet 2 Bed Room Apt W/ Private Entrance.
1 4
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.
9.5 55 reviews
Middletown, CT
08/07 – 09/07
NZ$1137/nightfor 1 night
#40 - Spacious, Sleek & Cozy *Sleeps 10*
1 4
apartment , Middletown
This spacious house in Middletown is located just 32km from the town centre, offering easy access to local attractions, shops and restaurants. The property features three bedrooms, two bathrooms, a fully equipped kitchen, a large dining room, a separate living room with a fireplace, and a spacious garden, comfortably accommodating up to eight guests.