
House vacation rentals in Middletown
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Top-rated house rentals in Middletown
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Popular amenities for Middletown house rentals
House rentals with a pool

The Getaway-HOST & Co.
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.

Pool House
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!

Garden Level Suite with Beautiful Pool
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!

East Hampton Oasis - Pool and Hot Tub
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!!

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

Large heated pool, games room, near private beach
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.

Stunning Views, Bucolic Bliss in 1790s Farmhouse
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.

Casino Stay & Play House
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

Country getaway - huge yard, pool
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.

Adorable Beach House on LI Sound
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.

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

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

Luxury Modern Hideaway
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!

Urban Luxury in Central CT w/ free RV parking
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!

Lakeside Paradise with Breathtaking Sunsets
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!!!

Modern Luxury, The Perfect Getaway Awaits
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

Boulder Lake House Retreat
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.

Stylish Modern Home, 4-Bedroom, Madison CT
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.

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

Private Woodland Sanctuary—3 mins to a lake beach!
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.

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

Coast and Country Private Estate
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.

Historic House by the River
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.

Field of Dreams Hot Tub - Fire Pit Retreat
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
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- Beach
- Fairfield Beach
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Cooper's Beach, Southampton
- Shinnecock Hills Golf Club
- Walnut Public Beach
- TPC River Highlands
- Ocean Beach Park
- Thunder Ridge Ski Area
- Woodmont Beach
- Amagansett Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Quotonset Beach
- Groton Long Point South Beach
- Kent Falls State Park
- Wildemere Beach
- Cedar Beach
- South Jamesport Beach
- Groton Long Point Main Beach