House vacation rentals in Cheshire

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Popular amenities for Cheshire house rentals

House rentals with a pool

Guest favorite
Home in Montville
4.92 out of 5 average rating, 272 reviews

Casino Wine Down House

EsperanzaRating, 5 stars1 day ago
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back
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.
Superhost
Home in East Hampton
4.88 out of 5 average rating, 111 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

MariaRating, 5 stars2 weeks ago
Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.
Top guest favorite
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!
Guest favorite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 starstoday
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 favorite
Home in North Fork
4.97 out of 5 average rating, 151 reviews

Secluded Farmhouse - Studio Apartment Style Unit

LeslieRating, 5 stars2 weeks ago
Jessica's place was serene and exactly what we were looking for during our long weekend in the North Fork. Great communication!
Guest favorite
Home in Sag Harbor
4.86 out of 5 average rating, 266 reviews

Exclusive Sag Harbor Compound

RobertRating, 5 stars2 weeks ago
Benjamins place was a wonderful stay for our family. Coming from the City it was amazing to have so much grass with peace and quiet. It is a short walk to the Main Street and Sag Harbor downtown. We had planned to go out and enjoy some activities during the couple of days we stayed but instead found the place so relaxing we spent most of it in the home. The separate house was nice for a master bedroom and quiet. We would highly recommend this house to anyone wanting to have a relaxing and quiet vacation in the Hamptons near Sag Harbor. Hope to be back again!
Top guest favorite
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars2 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.

Weekly house rentals

Guest favorite
Home in Branford
4.97 out of 5 average rating, 33 reviews

Adorable Beach House on LI Sound

JordanRating, 5 stars2 weeks ago
Had an excellent stay at Eileen’s place. The house was extremely clean and perfect size for a couple. Beautiful view and surroundings. Only wish I had more time to explore the area. Would definitely stay here again if I return.
Top guest favorite
Home in Plymouth
4.98 out of 5 average rating, 41 reviews

Don’t miss out on this cozy New England escape!

PriscillaRating, 5 stars3 days ago
Shawn's home provided a perfect place for my husband, mother and myself spend time with my son and daughter-in-law that are now attending college in CT. The home was spacious and made it possible for us to cook and to gather around a table for a family meal. The hot tub, fire pit table and grill was a great addition. There are also plenty of games available. The beds are super comfy! We wanted to take advantage of the skatepark but no one brought a board :-( The property and home are very beautiful. We had such a great time and won't forget how peaceful our stay was. Shawn is very responsive, informative and polite. Thank you for a wonderful stay.
Top guest favorite
Home in Westville
5 out of 5 average rating, 70 reviews

Westville Schoolhouse by Stephanie and Damian

TashicaRating, 5 stars1 week ago
Where to start! I could write an epistle about my stay but I'll keep it short and sweet. What an absolutely beautiful and stunning home! from the moment I arrived I felt right at home. Stephanie and her husband put a lot of thought into every detail of their home and they went above and beyond to ensure our stay was perfect. I wish I had an extra week! I appreciated how central the location is but still allows you to feel as though you are in a private oasis. I can't wait to be back in New Haven to rent from Stephanie again! you are a super host for a reason :) Thanks for making your home my home. My family and I truly enjoyed our stay. Already planning my next trip!
Top guest favorite
Home in New Haven
5 out of 5 average rating, 66 reviews

3BD w/ Hot Tub + FRER EV | Close 2 Beach +Yale

ShebellRating, 5 stars5 days ago
Wow, I don’t even know where to start! My family and I just had the most incredible time celebrating my niece's 21st birthday. From the moment we arrived, Annie blew us away as the ultimate host! The house was decked out with beautiful decorations that truly made the surprise unforgettable. And guess what? She even had a magnificent birthday cake waiting for us! The house itself was absolutely gorgeous and so inviting. We felt right at home with an abundance of linens, towels, and toiletries—perfect for a group of five women! The jacuzzi was a dream, and the grill was all set for us to fire up some delicious meals. Plus, the kitchen was stocked with all the essentials and some delightful extras! Annie was always quick to respond to our questions, which made everything even easier. We were thrilled to find beach necessities already available, so we didn’t have to worry about bringing our own. There’s so much more I could rave about, but overall, this stay was amazing.
Superhost
Home in Watertown
4.8 out of 5 average rating, 44 reviews

Cozy Cottage

KatieRating, 5 stars1 week ago
This was the perfect place to relax after visiting family all day. Hector's place was clean, private, and peaceful. the drive way is a little hard to find but GPS will get you there fine. The airbnb had everything we needed and loved the back deck for grilling. highly recommend.
Top guest favorite
Home in Watertown
4.96 out of 5 average rating, 24 reviews

Carriage House on Smith Pond!

IreneRating, 5 stars2 weeks ago
Another great stay for us at Todd's Airbnb. Once again we thoroughly enjoyed the ambience of the setting, the lovely views, and of course.....the treats that Janet thoughtfully provided. The Carriage house is very well equipped with a comfy bed and is extremely clean; we can highly recommend it.
Superhost
Home in Meriden
4.75 out of 5 average rating, 85 reviews

Relax by the water in a 4 bedroom house

MadelinRating, 5 stars1 week 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.
Guest favorite
Home in East Hampton
5 out of 5 average rating, 19 reviews

CT River Retreat - Modern Home with CT River Views

BrianaRating, 5 stars1 week ago
We had an amazing stay at Peter’s home by Saint Clement’s Castle for our wedding weekend! From start to finish, Peter was an exceptional host—friendly, responsive, and incredibly flexible with the details of our stay, which helped make a busy and emotional weekend so much smoother. The home itself was spotless, modern, and thoughtfully maintained. Every room felt comfortable and inviting, and the clean, updated aesthetic made it the perfect place to relax between events and get ready for our big day. It truly felt like a peaceful retreat during a very special time in our lives. We couldn’t have asked for a better experience and would absolutely recommend Peter’s place to anyone visiting the area—especially for events at Saint Clement’s. Thank you again, Peter!

Private house rentals

Superhost
Home in North Branford
4.9 out of 5 average rating, 10 reviews

The Gait House at High Gait Farm

NancyRating, 5 stars1 week ago
Lori was very accommodating to us with early check in. The beds were super comfortable, and I was so happy to see that she had two king sized beds and one queen! Perfect for our family. Beautiful linens, tons of comfy white towels in the bathrooms. Really a great place to stay that I would highly recommend.
Superhost
Home in New Haven
5 out of 5 average rating, 13 reviews

The Jewel of The Cove - Historic Coastal Retreat

MarkRating, 5 stars1 month ago
This home was gorgeous and impeccably decorated. We were in town for our daughter’s graduation and when we come back in three years when she gets her graduate degree we hope that this home is available again. Check in and check out couldn’t have been much easier. We highly recommend Edward, he was a great host.
Guest favorite
Home in West Haven
4.95 out of 5 average rating, 43 reviews

Westshore Luxury

MatthewRating, 5 stars1 day ago
You, was great. Traveling through and not knowing much about the area. Yu gave us so much helpful information. Be sure to ask Yu about their great restaurant in New Haven.
Top guest favorite
Home in Wallingford
5 out of 5 average rating, 62 reviews

New England Charmer

KathleenRating, 5 stars3 weeks ago
Family of 3 stayed 4 days but had 3 dinner guests while in New Haven area for Yale graduation. I'm glad we had our own car to transport us to Yale campus. Easy access to the freeway. House is beautifully decorated and color scheme. Nice dinner room table for 6 people to sit comfortably. Great kitchen although we did no actual cooking as we bring in take out meals. Great back porch and deck to sit at for visiting. Front street is a bit busy but deck in back is quiet from traffic noise. Able to use washer/dryer which has nice as we had been on the road for several days. All bedrooms are upstairs and stair steps are somewhat steep to bedrooms and basement. So for older folks the steps may feel a bit daunting. Nice shower. I haven't stayed in many Air B&B's so I don't know what is actually provide for the little extras but, I would recommended luggage stand in each bedroom, extra cloth dish towel in kitchen, kleenex and paper towel, hair dryer. Recommend over all.
Guest favorite
Home in Haddam
4.97 out of 5 average rating, 29 reviews

The Farmhouse Stay

MarisaRating, 5 stars2 weeks ago
Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!
Top guest favorite
Home in New Haven
5 out of 5 average rating, 52 reviews

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

ColleenRating, 5 stars3 days ago
This is a great place close to downtown and the university. The communication was timely and everything in the house was thoughtful and easy to navigate. It was a perfect place for our family to use.
Top guest favorite
Home in Haddam
5 out of 5 average rating, 22 reviews

The Doll House

EthlynRating, 5 stars2 days ago
Jeremy’s “Doll House” was a charming little place on lovely peaceful grounds. The location was very convenient for visiting our Connecticut relatives and attending our granddaughter’s graduation. His kitchen is well stocked with all the essentials and then some. Everything was very clean and the bed was very comfortable. There is a huge walk in closet in the bedroom and great laundry area in the bathroom. I would recommend Jeremy’s place and would stay there again.
Guest favorite
Home in Bristol
4.89 out of 5 average rating, 28 reviews

Entire home in Bristol

StacyRating, 5 stars1 month ago
Thanh’s place was extremely clean, comfortable, and private. Entrance instructions were prompt and easy to understand. It was perfect for our visit to the area. Thank you very much, Thanh! :)

Quick stats about house rentals in Cheshire

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 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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