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 stars4 days 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 Saugerties
5 out of 5 average rating, 33 reviews

Creekside in the Catskills

EsraRating, 5 stars1 month ago
We had a wonderful stay amidst a snowy winter wonderland! The house was so spacious and had everything we needed. The beautiful view of the creek bay, plenty of sunshine and gas fireplaces made it cozy and perfect for our family to relax and enjoy time together. Would highly recommend.
Top guest favourite
Home in Hillsdale
5 out of 5 average rating, 55 reviews

Lakefront close to ski & shopping

ChelseaRating, 5 stars1 month ago
This was my second time staying at this beautiful home on Copake Lake and this stay was even better than the first! We had two families of 5 and found the home to have plenty of space to all come together as well as spaces for quiet time alone. The road to the home was well maintained despite snowy/rainy/icy conditions. It was a breeze to get to and from Catamount ski resort. We cooked all of our meals in the home and the kitchen was well stocked with everything we needed. My kids are now begging to go back during the summer when the lake is not frozen solid. We will definitely recommend this home to others and hope to be back again!
Top guest favourite
Home in Granby
5 out of 5 average rating, 6 reviews

Lake house retreat Granby CT

ChristeRating, 5 stars4 months ago
WENT FOR A FAMILY CELEBRATION FOR THANKSGIVING WEEKEND. THE HOUSE WAS INCREDIBLY STUNNING, GREAT ENTERTAINMENT AREAS, PLENTY OF SEATING, BEAUTIFUL KITCHEN. EVEN THOUGH IT WAS THE END OF NOVEMBER, WE STILL WERE ABLE TO USE ALL THE OUTSIDE AMENITIES, THE OUTDOOR BAR, SEATING AREA, FIRE PIT, THE HEAT LAMPS WERE PERFECT & UNEXPECTED. THE OUTDOOR AREA WAS AS AMAZING AS INSIDE. THE HOUSE WAS BETTER THAN WE EXPECTED, WOULD HAVE TO SAY PERFECTION! CANNOT WAIT TO GO STAY AGAIN. THANK YOU TO NATHANIA, YOU'RE COMMUNICATION WITH US WAS QUICK & GREATLY APPRECIATED! LOVED EVERY MINUTE!
Top guest favourite
Home in Millerton
4.97 out of 5 average rating, 175 reviews

Vacation Home In Millerton

AnnaRating, 5 stars4 days ago
We had a fantastic time on our Girls' Weekend! The place was beautiful, exactly as she described. We were all so impressed with the indoor space, the outdoor space, the cleanliness, amenities, full kitchen, bedrooms - it was exactly what we were looking for and all of us had a great time! Thank you again!
Top guest favourite
Cabin in Cornwall
5 out of 5 average rating, 46 reviews

Beautiful Cabin in Cornwall CT.

RachelRating, 5 stars1 month ago
Henry’s place easily fit the needs of our group (three families with little kids) and had plenty of bedrooms for us to spread out between. We appreciated the large couch / living room area which was large enough for us all to comfortably sit. It’s a quick drive to the town of Kent which was very cute to explore (and lots of good places to eat!). We have friends in the area and would definitely book here again for a return trip. Check out was a breeze and we greatly appreciated not having a long list of to do items like other Airbnb’s.
Guest favourite
Home in New Milford
4.94 out of 5 average rating, 31 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars2 weeks 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 favourite
Home in Athens
4.9 out of 5 average rating, 10 reviews

Cozy Catskill Getaway by Hudson

AmirRating, 5 stars3 months ago
My friends and I had a wonderful weekend stay in Athens and the surrounding Hudson and Catskills area. The home was plenty of room for the five of us and we enjoyed the fireplace and hot tub amenities.

Destinations to explore