Holiday rentals in Winchester

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Popular amenities for Winchester holiday rentals

Stay near Winchester's top sights

Burr Pond State Park15 locals recommend
Gilson Cinema & Cafe14 locals recommend
Mario's Tuscany Grill11 locals recommend
Stop & Shop8 locals recommend
Noujaim's Food & Catering5 locals recommend
Little Red Barn Brewers5 locals recommend

Other great holiday rentals in Winchester

Top guest favourite
Home in Athens
5 out of 5 average rating, 38 reviews

Perfect 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 reviews

Lakefront 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 reviews

Lake 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 reviews

Vacation 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 reviews

Large & 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 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.
Top guest favourite
Home in Great Barrington
5 out of 5 average rating, 13 reviews

Great 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 reviews

Lakeside 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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