Photo by Donny Campos

Search Vacation Homes in Winchester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

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

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (17)
"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, (40)
"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

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths

Large Home in Greenfield Sleeps 8, w/4 bedrooms & 3 baths

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)
"The host was very welcoming. House has a great layout for a family/group and is beautiful. Loved the handmade pottery. Easy to get to and close to skiing, food, hiking etc."
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, (51)
"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

The Harrisville Ranch - Monadnock Region Getaway!

10.0 out of 10, Exceptional, (2)
"We booked a longer stay over the holidays and we were very pleased with the accommodations. The property was clean and very spacious, on a wooded lot that was pleasant and quiet. It was like a home away from home during our stay. We would definitely recommend!"
The Harrisville Ranch - Monadnock Region Getaway!

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)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

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!

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

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
10.0 out of 10, Exceptional, (14)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
The price is AED 621
AED 1,080 total
includes taxes & fees
12 Feb - 13 Feb
Beautiful Adirondack Cabin with Sauna 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.