
Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Winchester
Top guest favourite

Home in Athens
5 out of 5 average rating, 38 reviewsPerfect home for a getaway from NYC
ScottRating, 5 stars3 weeks ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top guest favourite

Home in Hillsdale
5 out of 5 average rating, 56 reviewsLakefront close to ski & shopping
KathyRating, 5 stars2 months ago
A beautiful home and the views were breathtaking on the lake. Although, it was frozen. All the amenities we needed and more. Close to skiing and tubing. Owner Sara was very attentive to respond quickly. We just wanted a getaway place for a family weekend. The road was narrow and very icy. Would go back but not in the winter. Summer and the Fall I think would be best. Lots more things to do in the nicer weather months. Thank you Sara for your hospitality.
Top guest favourite

Home in Granby
5 out of 5 average rating, 7 reviewsLake house retreat Granby CT
DianeRating, 5 stars1 week ago
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!
Top guest favourite

Home in Millerton
4.97 out of 5 average rating, 181 reviewsVacation Home In Millerton
SarahRating, 5 stars1 week ago
We had a wonderful week at Corina's house while out for a family event! The house was spotless and the kitchen was stocked with everything we could need. The outside space was just as amazing. We had a great campfire one night, enjoyed using the grill, and our dog loved being able to run around the large yard. I'm sure we'll be back next year!
Guest favourite

Chalet in Athens
4.86 out of 5 average rating, 49 reviewsLarge & Sunny Lakefront Home-kayaks/fire pit/games
KatieRating, 5 stars4 days ago
This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.
Top guest favourite

Cabin in Cornwall
5 out of 5 average rating, 47 reviewsBeautiful 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.
Top guest favourite

Home in Great Barrington
5 out of 5 average rating, 13 reviewsGreat Barrington Ranch. Sleeps 10,Hot Tub, 5 acres
JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Guest favourite

Home in Athens
4.96 out of 5 average rating, 23 reviewsLakeside home with Private dock and more !
Tzirel LeahRating, 5 stars3 weeks ago
Amanda’s home was the perfect place for a weekend getaway with friends. We enjoyed the comfortable living space, fireplace as well as the nice amount of bedrooms. We cooked in the kitchen and ate in the house and it was the perfect setup. Thank you for an enjoyable stay!
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- Yale University
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Six Flags New England
- Woodmont Beach
- Walnut Public Beach
- TPC River Highlands
- Taconic State Park
- Thunder Ridge Ski Area
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- The Connecticut Golf Club
- Burwells Beach
- Fort Trumbull Beach
- Bayview Beach
- Wildemere Beach
- Anchor Beach
- Opus 40
- Hartford Golf Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Morningside Beach
- Altschuler Beach