A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchester holiday homes

A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

1. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is £82
includes taxes & fees
3 Nov - 4 Nov
Cozy Vermont Tiny Home Get Away
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (3 reviews)
"The property was adorable, clean and had everything we needed. Even though it rained all weekend we still had the best time. Great, private location with amazing views and close to downtown Keene. The host was very responsive and made sure we were comfortable and had all the info we needed."
United States
Marie M.
The price is £224
includes taxes & fees
10 Nov - 11 Nov
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

3. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is £287
includes taxes & fees
13 Oct - 14 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

4. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is £373
includes taxes & fees
13 Oct - 14 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

5. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is £176
includes taxes & fees
4 Nov - 5 Nov
Lovely 2nd Floor Apartment
A garden with a wooden pergola, purple flowers, and a river view.

6. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (64 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is £200
includes taxes & fees
28 Oct - 29 Oct
Family Friendly Hilltop House In Putney Vermont
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

7. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is £167
includes taxes & fees
9 Nov - 10 Nov
Private bed with En-suite bathroom Marigold Room
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

8. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (10 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is £298
includes taxes & fees
20 Oct - 21 Oct
Enjoy your stay in an antique home in an antique toy museum!
A hallway with wooden flooring, white walls, and a bed in the background.

9. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is £321
includes taxes & fees
21 Oct - 22 Oct
Cozy private 2 bed apartment in Shelburne Falls
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

10. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is £123
includes taxes & fees
13 Oct - 14 Oct
The Eagles Wing at The CHM - Private Apartment
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

11. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is £511
includes taxes & fees
13 Oct - 14 Oct
Spacious 5BR w/ Hot Tub & Games
A lakeside residential area with houses along the water's edge, a dock, and a boat.

12. 3br Lakefront Oasis in Shutesbury with central air and 180-deg views!

3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
Shutesbury
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the house. Perfect for family and young kids. Very clean. View of lake and bald eagles! were amazing. Host was very responsive and provided a lot of extra info on location places to eat, events, etc. Would definitely stay again."
United States
Tara I.
The price is £583
includes taxes & fees
1 Nov - 2 Nov
3br Lakefront Oasis in Shutesbury with central air and 180-deg views!
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

13. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is £508
includes taxes & fees
2 Nov - 3 Nov
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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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Top Winchester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"The room was clean. Staff was very friendly. The breakfast was OK. Exactly what I needed."
John 2-night trip
Posted 3 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
175
Accommodation
132 Holiday Homes
Lowest Price
£82
Highest Price
£583