
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.

Amazing Oasis Private Pool, BBQ, Pool Table.
Glenda was friendly and had great communication from Start to Finish. This was a nice location for a family fun weekend. Although the drive is close enough to stores if you need anything (target/stopnshop/bjs etc), the property is in a quiet and safe neighborhood. The yard is a great place to hang out and relax with the fire pit or have fun in the pool. And when the weather was crappy the pool table and hanging out in the basement den was nice. Everything in the house is labeled and easy to find. We enjoyed the space and would definitely recommend. Thanks again! 😊

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!

Hot Tub and pool Home away from home
Jan's house was a great stay with plenty of room for six adults. We loved the game room and outdoor hot tub. Instructions for the hot tub were clear and easy to follow. We'd definitely stay again!

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.

Meeker Hill House - Country Escape w/ Heated Pool
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend

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.
Weekly house rentals

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.

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.

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
I stayed at Andrea’s place for the weekend with some friends as we were attending an event nearby. Andrea was very quick to respond, friendly, and extremely helpful; an all around great host! Her place is exactly as described, very clean, and stocked with everything we needed. I would highly recommend staying here!!

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.

Luxe Lake House Retreat Between Boston & New York
The place is so peaceful and gorgeous, almost like being in a nature preserve but not far from anything either. We saw deer, a fox, a heron, and lots of adorable chipmunks. It was the perfect place to stay during a graduation weekend where the town was bustling and we needed a place to decompress when not on campus. The lawn is simply stunning, and there are incredible views on the the pond and the sky from pretty much every room in the house. We were there during a wet spring and everything was green and fresh. It must be spectacular in the fall or during a snowy winter. Shawn is a super kind, attentive host. We hope to come back in 3 years for our next graduation! Thank you for letting us stay here!
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!

Warm Woodland Retreat
Zach is really proactive and kind. He left me alone , which is what I needed for this short trip, but made me feel like if I needed anything (recommendations, assistance, communications) he would be responsive and quick. The place is a cool New England house with a lot of charm. The neighbors are respectful and quiet. Youre minutes away from a lot of great Connecticut icons and Uber is accessible and cheap. I hope to stay here agin when I return in Sept. The upstairs room is challenging if there are mobility concerns - I would try to book the lower levels. All was wonderful and Zach was kind.

Westshore Luxury
Yu's home was outstanding. We walked into a pristine, spacious home with off-street parking and a short walk to the beach. The amenities were just what we needed for our one-night stay. We would stay at Yu's beautifully decorated home again.

Urban Luxury in Central CT w/ free RV parking
This was great place for myself and a few friends to stay at for two nights while in town to watch the Travelers Championship. The place was extremely clean and well stocked. Tim was very quick to respond and helpful with everything.

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

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.

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.

3BD w/ Hot Tub + FRER EV | Close 2 Beach +Yale
A lovely cozy home!!! We were in town for a lacrosse tournament and it was so nice to come back to the house and relax after a long day on the fields- also a very well stocked kitchen to make food. A nice running/walking path at the park down the road too. Annie gave lots of recommendations and responded immediately when I reached out. An excellent home and an excellent host. Couldn’t ask for anything better!!!
Quick stats about house rentals in Cheshire
Total rentals
10 properties
Nightly prices starting at
₹2,580 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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- 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