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Compare 98 Vacation Homes in Winchester with updated reviews, rates, and availability.

Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (30)
"We had a wonderful, quiet and relaxing time. Plenty of rooms for every guest. The veranda is very special. We will go back again and we would recommend it. The Host, Beth, was welcoming and helpful."
Beautiful, private log cabin with huge, relaxing screened porch
Lovely 2nd Floor Apartment
9.6 out of 10, Exceptional, (8)
"Lovely place! Very clean. Excellent communications with our host! Very homey!"
The price is $201
includes taxes & fees
$180 per night
Sep 29 - Sep 30
Lovely 2nd Floor Apartment
Peaceful 3-BR Cabin 40-Min to Stratton
2.0 star property
10.0 out of 10, Exceptional, (2)
"To say that this cabin had everything that you could want or need is an understatement! My family and I stayed for a week and during checkout my daughter choked up talking about the great time our family had. We left so rested. "
Peaceful 3-BR Cabin 40-Min to Stratton
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, (2)
"I justvwant to say thanks again for letting us stay in your beautiful home. We had great meals cooked in the large kitchen, and a fun time playing in the gym. Thank you Marcella!"
River Wine Inn is a GAMERS haven on 24 acres with a wooden bridge, river & pond
360 degrees of nature from within the 1 bedroom Vermont Mirror House.
10.0 out of 10, Exceptional, (13)
"Such a cool property! We can only imagine what its like when there is snow on the ground, it must be even more enchanting than it was during summer! Very zen environment! We will be back!"
The price is $446
includes taxes & fees
$398 per night
Sep 24 - Sep 25
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
Beautiful Custom Built Timber Frame Home, Sleeps 11
10.0 out of 10, Exceptional, (99)
"We had a fun, relaxing family weekend here. Nice space that easily fit all of us. Appreciate the responsiveness of the owner. "
Beautiful Custom Built Timber Frame Home, Sleeps 11
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
9.4 out of 10, Exceptional, (15)
"We had a fun time enjoying the view and playing board games plus outdoor pursuits. Thanks for sharing your home."
Rustic, dog-friendly escape with private pool, sweeping views, & W/D
Quiet private pond getaway
9.8 out of 10, Exceptional, (6)
"This bungalow was perfect for our weekend away! Very clean and the dock on the pond was the perfect touch. the property manager responded to my question super quickly as well. We would love to visit again soon! :) "
Quiet private pond getaway
Bright three-level home with water views, jetted tub, firepit, and pool table
8.2 out of 10, Very Good, (22)
"This is a beautiful log cabin! Setting is quiet and picturesque and easy to find. The house is well maintained and has everything you need. We cooked in all nights and enjoyed the firepit in the cool spring weather. On arrival house was immaculate, beds made and towels set out. They provide a book of brochures on what to do in the area. Not to miss- the North River bakery right down the street! They have a great selection and even have prepared family meals to go. We will be staying again!"
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, (36)
"My wife and I were looking for a nice cottage in the woods, and this place was perfect. It was only a few minutes from the main road, but felt like we were in the deep woods. It had a charming feel of a backwoods cabin with all the amenities needed for comfortable living. There were plenty of great hiking trails within 30 minutes as well as a number of quaint Vermont towns. It was the perfect spot to get away for a long weekend."
Cozy cottage tucked away in the woods
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (46)
"The house was just as described, we could walk from the property to the trail that was only a few hundred feet from one of the streams that feeds West River. The pool was a big hit! Not heated but the solar cover kept the water nice, and the grill down by the pool was great for having lunch. 3 generations truly enjoyed our stay and we were able to see some amazing wildlife. Lots of places to hike and enjoy the River and falls. Jelly mill falls was one of our favorites. Jordan was...
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
6 Bedrooms, 2 Offices, Internet, River, New England village charm
9.6 out of 10, Exceptional, (57)
"Stayed with six friends for the weekend. Comfortable."
6 Bedrooms, 2 Offices, Internet, River, New England village charm
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain
9.0 out of 10, Wonderful, (18)
"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
Historic Home w/ Modern Updates on < 4 Acres
10.0 out of 10, Exceptional, (5)
"The property was awesome! Old, quaint and brought memories back of our grandparents homes…Family sat around table and enjoyed shared memories"
Historic Home w/ Modern Updates on < 4 Acres
Hillside 5-BR Retreat 10-min to Mount Snow
10.0 out of 10, Exceptional, (3)
"Perfect communication , beautiful house, fantastic location, super service. Sauna, grill, dining outside and inside option and beautiful view from terrace."
Hillside 5-BR Retreat 10-min to Mount Snow
NH TREEHOUSE LIFE - Stay in a real treehouse!
10.0 out of 10, Exceptional, (11)
"Fantastic stay out in the wilderness! Very gracious and hospitable host, it was an AMAZING weekend! Would highly recommend and will probably be back! "
The price is $372
includes taxes & fees
$343 per night
Sep 24 - Sep 25
NH TREEHOUSE LIFE - Stay in a real treehouse!
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
LAKE FRONT: Cozy 4-bedroom lake camp with WiFi and an outdoor firepit!
2.0 star property
9.0 out of 10, Wonderful, (2)
"Cozy lake cottage that offers the rustic feel with cozy accommodations. If you are wanting luxury this is not for you. This ideal for those who appreciate lake life while offering northern Massachusetts vibes in local towns. We were there for a disc golf tournament at maple hill. Location was great to fit in a few other courses as well. "
LAKE FRONT: Cozy 4-bedroom lake camp with WiFi and an outdoor firepit!
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Other property types in Winchester

Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (30)
"We had a wonderful, quiet and relaxing time. Plenty of rooms for every guest. The veranda is very special. We will go back again and we would recommend it. The Host, Beth, was welcoming and helpful."
Beautiful, private log cabin with huge, relaxing screened porch
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (28)
"We had a wonderful time staying at the cabin. Enjoyed the space itself and the property. Quiet, private and peaceful. Looking forward to returning in the winter. "
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
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.