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House vacation rentals in Middletown

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Popular amenities for Middletown house rentals

House rentals with a pool

Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars4 weeks ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Top guest favorite
A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Superhost
An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.
Home in East Hampton
4.84 out of 5 average rating, 100 reviews

East Hampton Oasis - Pool and Hot Tub

MaryRating, 5 stars1 week ago
We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!
Guest favorite
The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.
Home in Montville
4.93 out of 5 average rating, 163 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

KacieRating, 5 stars2 weeks ago
We had a great time at AJ's place! The space is very spacious and comfortable, everything was clean, and the backyard was PERFECT for our group. Close to casinos and restaurants. Highly recommend for groups and families!
Guest favorite
A spacious pool area features a crystal-clear swimming pool surrounded by a wooden deck. Colorful sun loungers are arranged neatly, accompanied by large umbrellas offering shade. Lush greenery is visible in the background, enhancing the tranquil outdoor setting.
Home in East Hampton
4.93 out of 5 average rating, 154 reviews

Large heated pool, games room, near private beach

BerniceRating, 5 stars2 days ago
The house was perfect for my family. I loved the convenience of the one-floor layout and way it allows views of the pool and deck from the almost everywhere so we could enjoy it even when the weather didn't cooperate and we couldn't swim. The family /living room was comfortable and great for relaxing or watching a film. The lower level playroom was great fun with ping pong and billiards set up in two areas. We found everything we needed including electric outlets where you need them. The location was great for us and our rides to Montauk and the other towns in the area for museums and restaurants and views. The only thing less than perfect was low water pressure in the master bath sinks and shower, which Abigail said the plumber was addressing. She was extremely responsive and helpful.
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

PaulRating, 5 stars2 days ago
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.
Guest favorite
A circular above-ground pool is surrounded by a grassy yard, decorated with string lights that create a soft glow. The two-story house is visible in the background, featuring a deck area and large windows. Trees frame the space, adding to the serene setting.
Home in Montville
4.95 out of 5 average rating, 151 reviews

Casino Stay & Play House

NurisRating, 5 stars2 weeks ago
I loved spending my birthday with my family. It was the perfect place for my family. Everything was so clean and organized. I am very grateful for everything. Thank you

Weekly house rentals

Guest favorite
The historic two-family home is bordered by lush greenery and blooming flowers. A white picket fence frames the vibrant garden, while the house features dark shutters and a welcoming front porch. A winding pathway leads to the entrance, inviting guests into the serene surroundings.
Home in East Hampton
4.95 out of 5 average rating, 65 reviews

Country getaway - huge yard, pool

TressiaRating, 5 stars2 weeks ago
Lena was wonderful. She warmly welcomed me and my guest, making our stay very comfortable and easy. She even left me a note with birthday wishes, along with a box of delicious baked cookies. The apartment is charming and spacious, located on top of their home, with a large yard and peaceful scenery.
Guest favorite
A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.
Home in Branford
4.97 out of 5 average rating, 35 reviews

Adorable Beach House on LI Sound

JudyRating, 5 stars5 days ago
We had a wonderful stay at Eileen’s place. Many great restaurants close by…Lenny’s, Dockside and Rosso Vino we enjoyed. Delicious ice cream spots..Bishop’s Orchard Creamery and Ashley’s.
Top guest favorite
The exterior of a two-story waterfront home is shown, featuring a modern design with blue siding. A spacious deck is visible above a landscaped area with carefully arranged plants and gravel, while a driveway leads to the front of the house, surrounded by greenery.
Home in Rocky Hill
4.96 out of 5 average rating, 28 reviews

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT

BrentRating, 5 stars2 days ago
I highly recommend staying at the Riverside Blues House. It is in a charming location and a really well thought out property to stay. Liza really put a lot of thought into making the home not only comfortable but also very welcoming. From the moment I walked in the door you can feel the love in every room. The house is extremely clean with plenty of extras that made my stay very enjoyable. Thank you Liza!
Top guest favorite
The outdoor patio is illuminated, featuring a large hot tub and a dining area with a table and chairs. Surrounding the space are twinkling string lights, adding a cozy ambiance. A grill and lush greenery complete the inviting exterior setting of the home.
Home in Plymouth
4.98 out of 5 average rating, 42 reviews

Don’t miss out on this cozy escape! w/Skatepark

ChristopherRating, 5 stars4 days ago
Would gladly stay here again. Shawn was responsive and the place had everything we needed. Hope to come back to this part of CT again
Superhost
The living area features large windows adorned with striped curtains, allowing natural light to filter in. A black and white patterned rug anchors the space, with a glass coffee table and an accent table nearby. A minimalist art piece hangs on the wall above a sleek black bench.
Home in Meriden
4.78 out of 5 average rating, 9 reviews

Luxury Modern Hideaway

LauraRating, 5 stars3 months ago
I have stayed in a lot of Airbnbs but this one takes the cake for the price to value ratio. I absolutely loved the stunning decor and design of this home. I used it for some photography due to how beautiful it was. Thank you, we will be back!
Top guest favorite
The spacious living area features a large sectional sofa with plush cushions, arranged around a minimalist coffee table. A flat-screen TV is mounted on the wall above a stylish console. Natural light streams in through multiple windows, which are framed with light-colored treatments.
Home in Newington
5 out of 5 average rating, 41 reviews

Urban Luxury in Central CT w/ free RV parking

DonnaRating, 5 stars2 weeks ago
The home was in a beautiful neighborhood, which made for nice walks, the kids were able to play ball in the yard, the check in directions were clear, we had 2 vehicles with plenty of additional space, the house was squeaky clean, the beds were comfortable and the photos were very accurate. The ping pong table was awesome distraction when it rained. It was easy to get to stores and restaurants. Laser tag, movies, bowling all a short drive. Host was easy to reach, responded quickly and had friendly attitude. We can recommend the “Flying Monkeys” restaurant where we had dinner to live jazz band! Food was great. All in all despite clouds and rain we had a great time visiting with our grandkids!
Guest favorite
A serene lakeside view captures a vibrant sunset reflected on the calm water. The sky is filled with shades of orange and purple, framed by distant hills. A stone wall borders the foreground, leading into a pebbled area near the water's edge.
Home in East Hampton
4.88 out of 5 average rating, 26 reviews

Lakeside Paradise with Breathtaking Sunsets

MaileeRating, 5 stars3 weeks ago
Amazing house! We rented the lake house and guest house to spend time with family and friends during our son’s graduation at Wesleyan. I stayed in the guest house. It was so cozy with great modern amenities. It was the perfect place to relax and close to the school. Being close the lake was a definite plus. I highly recommend!!!
Superhost
A modern kitchen is showcased with sleek gray cabinetry and a large island, complementing the wooden flooring. Pendant lights hang above the island, adding warmth to the space. A dining area with a glass table is visible, featuring clear chairs and large windows that invite natural light.
Home in Middletown
4.75 out of 5 average rating, 4 reviews

Modern Luxury, The Perfect Getaway Awaits

JoyRating, 5 stars3 months ago
I wish I was staying more than 1 night!! it was beautiful, spacious, well stocked, beautifully decorated and cozy. Shakeema waa friendly and very responsive. The 4 of us had plenty of room to be. If I ever come back this way, I will absolutely stay here again!!!

Private house rentals

Guest favorite
A modern kitchen features a central island with three stools, surrounded by sleek countertops and essential appliances. Large windows and glass doors provide abundant natural light and a view of the outdoor area, seamlessly connecting the interior and exterior spaces.
Home in Clinton
4.89 out of 5 average rating, 18 reviews

Boulder Lake House Retreat

AmandaRating, 5 stars4 days ago
Great stay! Although it was a rainy weekend, we had a great weekend!! There were close restaurants and coffee shops and the house itself was perfect. Great aesthetic to the home, very cozy and relaxing.
Top guest favorite
Home in Madison
5 out of 5 average rating, 28 reviews

Stylish Modern Home, 4-Bedroom, Madison CT

AlanRating, 5 stars3 months ago
Sascha was a terrific host and we had a wonderful stay at his home. The home was beautiful: plenty of space to spread out, relax, and everything was incredibly clean and tidy. It was also well-stocked with everything you could need. We appreciated Sascha's friendly demeanor, and he was a pleasure to communicate with. We hope to return here in the near future for another stay.
Top guest favorite
A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.
Home in North Fork
5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

SamanthaRating, 5 stars1 month ago
Can not recommend more! Beautiful house and perfect location! Would love to come back. Kids loved the beach and finding shells and little sea creatures in low tide!
Top guest favorite
A multi-story wooden house is set against a backdrop of lush green trees. Colorful flowering bushes, primarily in shades of pink, enhance the natural landscape, while a glass solarium extends from one side of the house, showcasing outdoor living space.
Home in New Hartford
4.96 out of 5 average rating, 69 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

EmilyRating, 5 stars2 weeks ago
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.
Top guest favorite
A view of Lake Pocotopaug, framed by lush greenery. A spacious deck extends towards the water, furnished with outdoor seating. A yellow inflatable sits on the dock, which is accessible for guests. The tranquil lake is surrounded by gentle hills in the background.
Home in East Hampton
4.99 out of 5 average rating, 72 reviews

Lake Fun: PingPong, Pool Table, Slide, EV Charger

KylieRating, 5 stars1 week ago
We had a wonderful stay at this gorgeous lakehouse! Honestly, the pictures don't do the place justice. The lake was lovely, and the house was well-equipped and spotlessly clean. The furnishings and decorations were far nicer than you often find in an airbnb; it felt like a true home. Everything we could have possibly needed to enjoy the lake was provided, from canoes and kayaks to inner tubes, and the kitchen was well-equipped with all manner of cooking utensils and basic spices/condiments. Linda and Dick were great--very communicative and easy to get ahold of, but left us to our privacy otherwise. Would absolutely go back again!
Top guest favorite
A modern home is showcased with a stone foundation and large windows, allowing natural light to fill the space. A spacious deck is visible, featuring colorful seating options and a stone wall that surrounds a well-maintained lawn, complemented by leafy trees.
Home in Guilford
5 out of 5 average rating, 19 reviews

Coast and Country Private Estate

AndreaRating, 5 stars5 months ago
Suzanne’s home is beautiful and felt like being in our own home. The property is serene and very private. The house and kitchen were well equipped for cooking. Suzanne was so easy to communicate with pre during and post stay. We have family in the area so I hope to be back again.
Guest favorite
A charming two-story house features white siding and traditional dark shutters. A small American flag is displayed prominently at the front. The front yard is surrounded by greenery, and a driveway leads to a garage on the left side. Tall trees provide shade nearby.
Home in East Haddam
4.88 out of 5 average rating, 48 reviews

Historic House by the River

DhaniRating, 5 stars1 month ago
This house and host exceeded all expectations. House was historic facing the CT River & Goodspeed Opera House. Great sunsets. House is clean and well appointed with comfortable beds and bathroom facilities. Kitchen is spacious and eating areas comfortable. Andrea is extremely responsive and accommodating. Will be back again.
Top guest favorite
A hot tub is positioned on a deck, softly illuminated by string lights overhead. The deck area features a dining table and chairs, while the surrounding space is surrounded by a railing. The home is visible in the background, with warm light emanating from the windows.
Home in Guilford
5 out of 5 average rating, 61 reviews

Field of Dreams Hot Tub - Fire Pit Retreat

JoshuaRating, 5 stars3 weeks ago
Field of Dreams is a beautiful, spacious, well-appointed home. Brenda is an attentive, gracious, and thoughtful host. My family and I stayed there for four stellar days over Memorial Day for my daughter’s college graduation. We hosted a big family dinner with a private chef that was excellent. And Brenda really helped us with some of the details. This is a lovely home and I highly recommend it.

Quick stats about house rentals in Middletown

  • Total rentals

    50 properties

  • Nightly prices starting at

    R541 ZAR before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore