
Vacation rentals in Cheshire
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Top-rated vacation rentals in Cheshire
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Popular amenities for Cheshire vacation rentals
Other great vacation rentals in Cheshire

Spacious Classic Lakefront Home with jet tub
I came here in the dead of winter for a writer's retreat with a fellow writer- AND I WOULD DO IT AGAIN! It was a beautiful and inspiring place to write. Perched on Andover Lake, it was too cold to frolic outside but that was actually liberating. There was a rocking chair-ottoman combo in the master bedroom looking out on the lake and watching it freeze while I worked on some writing was so peaceful and perfect. When I needed to switch it up, there was a writer's desk with the same view and I can not overstate how nice and productive it was to work from it. I am sure in the summer it's a really fun stay (there were kayaks and a dock for swimming) but I actually loved being isolated in such an idyllic place. It's near a few other homes but the road was low traffic enough for a cold weather run around half the lake. Marcie was super helpful with suggestions for places to eat. We didn't actually use the recs - but that only speaks to how nice the house was and how hard it was to leave!

Beautiful Cabin in Cornwall CT.
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.

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

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

Beach House steps from sand & Amazing Views
Beautiful home with lovely views. Great kitchen for cooking. We had 8 of us and the house was spacious and welcoming for the group.

Sleek and Chic cottage/Pool House
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!

Beachfront paradise- come, stay, relax!
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!

Great Hammcock Getaway, Nearby beaches, Hot tub
What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.
Quick stats about vacation rentals in Cheshire
Total rentals
20 properties
Nightly prices starting at
$30 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.
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- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Quotonset Beach
- Six Flags New England
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Marvin Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Long Island Aquarium
- Groton Long Point Main Beach
- Attawan Beach
- Mohawk Mountain Ski Area
- Bushnell Park
- Sunken Meadow State Park
- Weed Beach
- West Beach
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