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Compare 109 Vacation Homes in Winchester with updated reviews, rates, and availability.

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (18)
"It was just as shown in the listing. Overall was very clean and comfortable. Futon took a little figuring out to get set up and securing the shower curtain to prevent spilling water on the bathroom floor took a do-over and some clean-up, but in general was very happy with our stay and the host was very courteous and responsive."
The price is AED 474
AED 792 total
includes taxes & fees
18 Feb - 19 Feb
Lovely 2nd Floor Apartment

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Cozy cottage tucked away in the woods

10.0 out of 10, Exceptional, (41)
"We loved this cabin in the woods. This was our second stay here. More than enough room for my wife and I and 26 year old daughter. Beautiful and rustic with a working wood stove and plenty of wood on hand. Kitchen is well stocked. Be warned that road access is a little challenging - steep unpaved road to get there - but our non-4x4 minivan could make it. Lots of good hiking in nearby Jamaica, and the neighboring small towns are charming. Craig was a great host and very responsive."
Cozy cottage tucked away in the woods

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

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

River House

2.0 star property
10.0 out of 10, Exceptional, (7)
"Everyone felt at home and loved the house, it was plenty big enough to spread out and have a good visit"
River House

The Dover Hideaway | Hot Tub & Close to Mt. Snow

The Dover Hideaway | Hot Tub & Close to Mt. Snow

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

10.0 out of 10, Exceptional, (65)
"My husband, myself, 3 of my adult kids and 5 grandchildren under 7 stayed very comfortably. So many nice rooms. Although very updated had a very nostalgic feel. All of the living spaces were extra large and plenty of seating. The kitchen had everything that we needed and the yard was humongous. We were fortunate to get snow while we were there and the kids had never seen snow since we’re from Georgia. It was a wonderful stay. Thank you so much, Wayne. "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Inviting mountain view home with game room, balcony & W/D

8.8 out of 10, Excellent, (8)
"We stayed at the Mountain View for a work field trip. We were celebrating the delivery of several pianos we rebuilt for the Yellow Barn I'm Putney. We spent most of our time outside, but when we came back, it was delightful. This is a beautiful property, very clean, and very cozy"
Inviting mountain view home with game room, balcony & W/D

Historic Home w/ Modern Updates on < 4 Acres

10.0 out of 10, Exceptional, (6)
"Stayed here with my brothers and cousins.. had a great time. Close proximity to Royalston Falls and a great hike through the forest "
Historic Home w/ Modern Updates on < 4 Acres

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (52)
"Anther fantastic time at this beautiful location. Owner is always so geeat to work work "
Waterfont log home nestled in the pines

Peaceful 3-BR Cabin 40-Min to Stratton

2.0 star property
10.0 out of 10, Exceptional, (4)
"A beautiful cabin with all the amenities to relaxThank you "
Peaceful 3-BR Cabin 40-Min to Stratton

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

10.0 out of 10, Exceptional, (4)
"Easily walkable to the very lovely village of Westmoreland, but secluded and with a beautiful view, really quiet and user-friendly. Attentive property owners checked in with us to make sure everything was okay, which was kind and made us feel at home. A terrific porch that's warm in the sunshine even in winter, with great views of birds, sky and stars. "
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (37)
"Beautiful.home, open living space, great location for skiing at mt..snow. wet, rainy weather made driveway ride to the home very muddy. Communication with the owner, Doug, was easy and he was very accommodating. Furniture is dated and some mattresses need replacing. "
Mount Snow Post and Beam House

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"House is comfortable and well stocked."
Nestled on the edge of the woods near Mount Monadnock

Relaxing Home Mins from Mt Snow, Hiking, & Lakes

10.0 out of 10, Exceptional, (4)
"Mark and David are very easy and helpful The property is excellent We will come back!"
Relaxing Home Mins from Mt Snow, Hiking, & Lakes

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

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (44)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A River Retreat

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

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
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.