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Compare 102 Vacation Homes in Winchester with updated reviews, rates, and availability.

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (48)
"The House, Lands and View of this place are all amazing. Great for big family gathering to escape and rejoice and relax. We came to explore a bit of Vermont, which we did, but we also found ourselves reluctant to go out as the house and property were so captivating all on their own!"
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
10.0 out of 10, Exceptional, (15)
"Great home in a peaceful location in the country. The place is perfect for a couple and has a cool basement living space."
The price is SAR 1,315
SAR 1,670 total
includes taxes & fees
6 Nov - 7 Nov
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (67)
"The house was clean and looked newly remodeled. It had everything we needed for our 3 night stay. It is a good location when visiting Western MA. We would stay there again. Western MA. "
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Hilltop Home with Great Views
9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!
9.8 out of 10, Exceptional, (110)
"Every need accommodated including a back-up generator! Well appointed kitchen and bathrooms. Very cozy and spacious home inside. Very comfortable bed mattress in master bedroom. Lots of yard for dogs to run free. Nature all around. Lots of books and board games there. Laundry room was a big plus. Remote setting but lots to see and explore within reach. Very lovely stay and hosts were very responsive."
Secluded Vermont Retreat w/ 25 Acres to Explore--Dog Heaven! Mountain Views!
Lovely 2nd Floor Apartment
9.8 out of 10, Exceptional, (15)
"Apartment was clean and a good location for what I needed. Everything required for a comfortable stay"
The price is SAR 447
SAR 780 total
includes taxes & fees
6 Nov - 7 Nov
Lovely 2nd Floor Apartment
Charming barn studio apt, in lovely Peterborough NH overlooking the downtown.
2.0 star property
10.0 out of 10, Exceptional, (2)
"Outstanding "
Charming barn studio apt, in lovely Peterborough NH overlooking the downtown.
Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (53)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is SAR 732
SAR 1,292 total
includes taxes & fees
6 Nov - 7 Nov
Family Friendly Hilltop House In Putney Vermont
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (42)
"A bit off the beaten path…but worth it! Such an immaculate, comfortable home. It is nestled within the gorgeous beauty of southern Vermont. You can be in Brattleboro for necessities in 20 minutes. There are so many wonderful walks you can take right outside your door. This was just the calm we needed toward the end of our 10 day trip. I would return in a heartbeat!"
Cozy Cottage Along Idyllic Green River
Bright three-level home with water views, jetted tub, firepit, and pool table
8.4 out of 10, Very Good, (25)
"We stayed three nights here. Just the two of us. I felt the pictures were misleading. Much smaller than expected. Since it was just the two of us it was perfect. "
Bright three-level home with water views, jetted tub, firepit, and pool table
Cozy cottage tucked away in the woods
10.0 out of 10, Exceptional, (37)
"This property is really “in the “woods” We enjoyed our stay, so peaceful. The foliage was beautiful. There was a lot of DVD’S to watch, no cable or regular channels. There was also a record player with many albums to choose from. Comfortable mattresses and pillows. Very well equipped with everything you need to prepare a meal at the house. River Bend Farm Market is about 15 minutes away and it has ready to go food, sandwiches, everything you need to find at a grocery store. Great communication...
Cozy cottage tucked away in the woods
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
10.0 out of 10, Exceptional, (64)
"House was large and comfortable with space for everyone. Enjoyed dinners with our group around the dining table. Kitchen is older but works. Played a charades-type game in the living room one evening. Peterborough wonderful for eats, walking and shopping. "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain
9.2 out of 10, Wonderful, (21)
"Nice relaxing time spent with my family skiing at Mount Snow. Only complaint would be the high fees associated with the property compared to others."
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
9.8 out of 10, Exceptional, (24)
"We had an amazing week at the Tyler House. The house and location are among the best on the lake. The host lives nearby and is happy to assist with any requests."
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Private Field House - Spacious 4 Bedroom Home
10.0 out of 10, Exceptional, (15)
"Very nice home, quiet location, and house had everything we needed and more. Property manager timely communicated all necessary information."
Private Field House - Spacious 4 Bedroom Home
Spacious pet & family-friendly, fastest wifi! Giant playset, fire pit, & games!
10.0 out of 10, Exceptional, (40)
"What a fun place to stay. Highly recommend for weekend away with kids. So much room for everyone to relax after skiing. Great location to mountain. Very clean and owner was so easy to get in touch with. Definitely will be back next year!!"
Spacious pet & family-friendly, fastest wifi! Giant playset, fire pit, & games!
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
10.0 out of 10, Exceptional, (12)
"Loved the location and property. Easy to work with Anthony very responsive"
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat
The Inn at Kampfires
3.5 star property
9.4 out of 10, Exceptional, (43)
"We very much enjoyed our stay. The people were super friendly and welcoming!"
The Inn at Kampfires
River Wine Inn is a GAMERS haven on 24 acres with a wooden bridge, river & pond
2.0 star property
10.0 out of 10, Exceptional, (3)
"This place was SO fun to stay at, and we did not have enough time during our 3 night stay to experience it all! The house is clean, the grounds are beautiful and scenic, and the location is near so many fun places to go. The amount of activities at the house alone gives you more than enough entertainment that you never even have to go explore, but the whole area is equally wonderful. The host was very communicative and helpful. Thank you for everything we hope to be back next year!"
River Wine Inn is a GAMERS haven on 24 acres with a wooden bridge, river & pond
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winchester

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (41)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (48)
"The House, Lands and View of this place are all amazing. Great for big family gathering to escape and rejoice and relax. We came to explore a bit of Vermont, which we did, but we also found ourselves reluctant to go out as the house and property were so captivating all on their own!"
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.