
House holiday rentals in Cheshire
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Top-rated house rentals in Cheshire
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Popular amenities for house rentals in Cheshire
House rentals with a pool

Private Oasis W/Stunning Vinyard and Pool Views
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

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.

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!

Midcentury Modern ZenHouse Sculptor Studio
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

Secluded Farmhouse - Studio Apartment Style Unit
This is a beautiful farmhouse setting with gorgeous gardens, chickens, a nice screened in private porch, and a very friendly and adorable kitty. Jessica was a great host and provided some delicious homemade yogurt with milk and fruit, and plenty of coffee and tea. We brought our dog and he was comfortable there, we had plenty of space to walk him around.

Port Jefferson Convenient, Cozy and Chic!
We we’re going to Port Jefferson for a family wedding. Our Airbnb was perfectly situated. There is a pool area that we never used because we just didn’t have time. But it looked very inviting. The town of Port Jefferson had plenty of nice restaurants and shops. This house was perfect for our situation. We had six adults, all family members.

Exclusive Sag Harbor Compound
Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!
Weekly house rentals

Walk to Choate, 3 Queens & 1 twin
Before I booked, Dean was very helpful to me as I figured out whether this stay fit my family’s needs. We particularly appreciated the first floor bedroom and the off-street parking behind the house. This home made it easy for us to visit family in the area. Thank you!

Westville Schoolhouse by Stephanie and Damian
Home was nice. Easy parking with your own driveway. Neighborhood is great for walks/runs. Close to coffee shops, restaurants, and Yale Bowl/Music Bowl. Great stay if coming to New Haven area.

Private 6-Bed House w/ King Bd, Groups & Families
Eva is a great hostess. We very much enjoyed staying in her house. She was very easy to communicate with whenever we had an issue. I definitely would like to have Eva as a hostess again and would like to stay in her house again.

Remodeled Historic Forestville Home w/fire pit
Beautiful home in a relaxing location. Maryann an A+ hostess. Quick to answer questions and make sure stay is comfortable. Kitchen is A+ equipped - much appreciated! Well located by many attractions within an hrs drive. Plenty of restaurants and coffee places to choose from within minutes. Home updated throughout, while maintaining its original character. We stayed an entire week and felt at home the entire time.

Carriage House on Smith Pond!
By far one of the nicest air B&B’s we’ve stayed in. Beautifully renovated carriage house on an incredible piece of property. Todd and Janet warmly welcomed us with their chickens’ fresh eggs, fruit and muffins. Kitchen was well equipped for preparing meals and we enjoyed dining al fresco while hawks flew and deer ran across the fields. Upstairs is a comfortable bed with nice linens and a large bathroom. This is a real gem! We hope to return in the future.

CT River Retreat - Modern Home with CT River Views
Amazing decor and views! The host was super responsive and professional. Lovely stay. Thank you!

Relax by the water in a 4 bedroom house
We had a great time at Tonya’s place visit CT from AZ with the family for nephew’s wedding. Convenient location, spotless and very comfortable it felt like home.

Cozy 3BR Yale Home - Ideal Getaway!
Had everything we needed, comfortable beds, great location, very clean
Private house rentals

The Gait House at High Gait Farm
Lori was an incredible host with excellent communication. Her home is charming and comfortable and she left us so many nice personalized touches. Would recommend to anyone visiting the area!

Adorable Beach House on LI Sound
There’s so much to love about this charming open plan beach cottage! We especially enjoyed the water views, hearing the birds, and eating on the breezy porch. It was sparkling clean and stocked with everything you’d need, from comfortable beds and towels to many thoughtful essentials like hand and dish soaps, tea and coffee pods, paper towels/toilet paper, and shampoo/conditioner. Eileen is a gracious and responsive host — she was particularly understanding when we had to reschedule our visit. Thank you for a wonderful stay, Eileen, and we hope to return!

Don’t miss out on this cozy escape! w/Skatepark
Shawn created a special place here. Love all the details, especially the skateboards and music room. The hot tub was lovely after a long day of driving, I soaked again in the morning. ColecoVision console in the game room was so nostalgic along with a great selection of other games. I really enjoyed the grounds. Even wandered down to the dam/waterfall. My mother in law, son and wife all had their own space to stretch out. I could easily spend more time here, it is not just a place to lay your head for the night.

Artist's Retreat In The Woods | Five-Acre Backyard
What a fabulous home! My family had a peaceful and enjoyable stay at this hidden gem! The home is spotless and has everything you need to feel at home, sleep well and cook! Thank you to a superb host!!

New England Charmer
Our family thoroughly enjoyed our stay at Erin’s immaculate, beautifully updated home. Great thought has been given for the comfort and convenience of guests. The new kitchen has plenty of cabinets with all the conveniences you would need for your stay. The individual air conditioners in all the bedrooms (upstairs) added to our comfort during our June trip and were appreciated on the couple of warm days we had during our stay. The downstairs temperature stayed cool enough without a/c, even on the one day that got to the high 80s. This is even nicer in person than the great online photos. Erin included a lot of extras to make our trip just perfect. She provided plenty of information, suggestions, etc. prior to our stay, and she was very responsive any time we had questions - both before and during our stay. We loved the sun porch, the deck and even the old fieldstone basement where the washer and dryer are located. Thanks, Erin, for making this a great place to stay. We will return

Trail-side Haven Retreat! Pet friendly
This property is in New Haven, bordering North Haven. Easily accessible from the 91 or from SR15, but not near enough either road to hear traffic noise. This is a downstairs unit, and there are tenants above; you will hear some neighborly noise, but nothing out of the ordinary for a duplex, and much quieter than a hotel room. If you're familiar with the area, this home is walking distance from the large Medtronic facility and a close drive to the North Haven shopping area (Target, Cinemark). Property is well kept, and all linens and interior areas were clean. We appreciated the pet-friendly approach (minimal rugs on the floor), as well as the large (unfenced) yard for our dog. We had a few minor issues, to which the hosts were quick to respond and remedy. The kitchen has every feature or appliance you'd need for a short stay, and even included common spices, soap, paper towels, and kcups. Bathroom had ample towels for 2 people. Would be happy to stay here for future visits.

The Farmhouse Stay
If you are looking for an amazing farmhouse with great views look no further. My family and I had the best week staying here. Communication was great and the house had everything that we needed. My wife and I still can’t believe how clean and organized everything was. We loved sitting by fireplace and watching movies at night. Definitely will be back if we are in the area

Historic Litchfield County Home
Yverose was wonderful. We couldn't have asked for a better spot to host our weekend get together. The house was beautiful and so comfortable - perfect for 6 girlfriends. We would love to be back one day!!
Quick stats about house rentals in Cheshire
Total rentals
10 properties
Nightly prices starting at
$38 SGD before taxes and fees
Total number of reviews
340 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
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- Fairfield Beach
- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- TPC River Highlands
- Shinnecock Hills Golf Club
- Ocean Beach Park
- Walnut Public Beach
- Thunder Ridge Ski Area
- Woodmont Beach
- Jennings Beach
- Bushnell Park
- Groton Long Point Main Beach
- Seaside Beach
- Silver Sands Beach
- Groton Long Point South Beach
- Quotonset Beach
- Sherwood Island State Park
- Calf Pasture Beach
- Sunken Meadow State Park
- Centerport Beach
- Cedar Beach
- South Jamesport Beach
- Brownstone Adventure Sports Park