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Vacation rentals in Cheshire

Find and book unique accommodations on Airbnb

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Popular amenities for Cheshire vacation rentals

Stay near Cheshire's top sights

Hubbard Park15 locals recommend
Costco Wholesale14 locals recommend
Farmington Canal Heritage Trail14 locals recommend
Toyota Oakdale Theatre11 locals recommend
Viron Rondo Osteria5 locals recommend
New Mill Restaurant4 locals recommend

Other great vacation rentals in Cheshire

Top guest favorite
Home in Andover
4.98 out of 5 average rating, 56 reviews

Spacious Classic Lakefront Home with jet tub

JeffreyRating, 5 stars3 months ago
The house felt like coming home. Everything you need was provided. The location is beautiful as is the surrounding area. We needed proximity to family and this was a perfect spot. All the amenities in the home were available and perfect for a weeklong stay. Thank you for a great stay!
Top guest favorite
Cabin in Cornwall
5 out of 5 average rating, 48 reviews

Beautiful Cabin in Cornwall CT.

JanRating, 5 stars2 weeks ago
Henry's beautiful home and yard provided the perfect getaway for 5 friends who try to get together at least once a year, coming from 3 different states. The large rooms, clean/fresh bed linens and towels, two full bathrooms and spacious living room adjacent to the kitchen gave us jus t the right setting in which to enjoy each other's company. Breakfast at the kitchen table overlooking the backyard was bright and sunny first thing in the morning. We especially liked the backyard patio, which gets sun all day long. After a cold rainy start to our stay, we were able to enjoy a warm afternoon on the patio - sunshine, blue skies, birds, budding trees and the soothing sound of the water fountain and small pond . We found great restaurants in both Kent and in Litchfield. As an avid gardener, I can just picture Henry's beautiful landscaping when all is in bloom later in the season. Very comfortable place to hang out! We wouldn't hesitate to give others a recommendation for Henry's home.
Guest favorite
Cottage in Norwalk
4.94 out of 5 average rating, 68 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

AdamRating, 5 stars1 week ago
We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!
Guest favorite
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries
Guest favorite
Home in North Fork
5 out of 5 average rating, 10 reviews

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

KristinaRating, 5 stars1 week ago
Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.
Superhost
Home in Cornwall
4.82 out of 5 average rating, 96 reviews

State Forest Getaway

GideonRating, 5 stars1 week ago
Elena's house turned out to be a great vacation spot for us. It was conveniently located, very well maintained and guest friendly. Though rustic on the outside, the interior was completely redone, offering all modern amenities you might want. Kitchen was better equipped than most Airbnb's we've stayed at and was fun for us to cook in Without getting into much detail I'll just say that should we be in the area again we'll definitely return to this Airbnb and always recommend it to others
Guest favorite
Guesthouse in Shelter Island
4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

YuryRating, 5 stars11 months ago
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Guest favorite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Quick stats about vacation rentals in Cheshire

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    530 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Gym, BBQ grill, and Laptop-friendly workspace

Frequently Asked Questions

  • Do house rentals in Cheshire have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Cheshire. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Cheshire?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Cheshire?

    Yes! Work meets play with ease at over 10 vacation rentals in Cheshire featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Cheshire?

    Experience the best of Cheshire with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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  5. Cheshire