House holiday rentals in Cheshire

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Popular amenities for house rentals in Cheshire

House rentals with a pool

Top guest favourite
Home in North Fork
4.97 out of 5 average rating, 206 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars1 month ago
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!
Superhost
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 favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars4 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!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars2 weeks ago
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.
Guest favourite
Home in North Fork
4.97 out of 5 average rating, 156 reviews

Secluded Farmhouse - Studio Apartment Style Unit

AmyRating, 5 stars3 days ago
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.
Guest favourite
Home in Port Jefferson
4.92 out of 5 average rating, 125 reviews

Port Jefferson Convenient, Cozy and Chic!

DaleRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Sag Harbor
4.86 out of 5 average rating, 269 reviews

Exclusive Sag Harbor Compound

Amy RoseRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 165 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MeredithRating, 5 stars6 days ago
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

Guest favourite
Home in Wallingford
5 out of 5 average rating, 5 reviews

Walk to Choate, 3 Queens & 1 twin

TiffanyRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Westville
5 out of 5 average rating, 73 reviews

Westville Schoolhouse by Stephanie and Damian

KyleRating, 5 stars6 days ago
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.
Top guest favourite
Home in New Haven
5 out of 5 average rating, 54 reviews

Private 6-Bed House w/ King Bd, Groups & Families

DavidRating, 5 stars1 week ago
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.
Guest favourite
Home in Bristol
4.97 out of 5 average rating, 68 reviews

Remodeled Historic Forestville Home w/fire pit

JohnRating, 5 stars2 weeks ago
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.
Top guest favourite
Home in Watertown
4.96 out of 5 average rating, 26 reviews

Carriage House on Smith Pond!

BetsyRating, 5 stars1 week ago
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.
Guest favourite
Home in East Hampton
5 out of 5 average rating, 21 reviews

CT River Retreat - Modern Home with CT River Views

NicoleRating, 5 stars3 days ago
Amazing decor and views! The host was super responsive and professional. Lovely stay. Thank you!
Superhost
Home in Meriden
4.75 out of 5 average rating, 85 reviews

Relax by the water in a 4 bedroom house

MadelinRating, 5 stars3 weeks ago
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.
Superhost
Home in North Haven
4.82 out of 5 average rating, 38 reviews

Cozy 3BR Yale Home - Ideal Getaway!

BetRating, 5 stars2 weeks ago
Had everything we needed, comfortable beds, great location, very clean

Private house rentals

Guest favourite
Home in North Branford
4.92 out of 5 average rating, 12 reviews

The Gait House at High Gait Farm

AllisonRating, 5 stars5 days ago
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!
Guest favourite
Home in Branford
4.97 out of 5 average rating, 37 reviews

Adorable Beach House on LI Sound

LisaRating, 5 stars5 days ago
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!
Top guest favourite
Home in Plymouth
4.98 out of 5 average rating, 45 reviews

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

WilRating, 5 stars5 days ago
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.
Guest favourite
Home in Roxbury
4.9 out of 5 average rating, 50 reviews

Artist's Retreat In The Woods | Five-Acre Backyard

JulianneRating, 5 stars1 week ago
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!!
Top guest favourite
Home in Wallingford
5 out of 5 average rating, 63 reviews

New England Charmer

KarenRating, 5 stars1 week ago
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
Superhost
Home in North Haven
4.83 out of 5 average rating, 36 reviews

Trail-side Haven Retreat! Pet friendly

KimberlyRating, 5 stars5 months ago
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.
Guest favourite
Home in Haddam
4.97 out of 5 average rating, 31 reviews

The Farmhouse Stay

BrianRating, 5 stars3 days ago
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
Superhost
Home in Watertown
4.92 out of 5 average rating, 24 reviews

Historic Litchfield County Home

CarterRating, 5 stars1 month ago
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

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