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

Holiday Homes in Winchester

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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 AU$152
includes taxes & fees
31 Oct - 1 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)
"This place was really beautifully appointed and thoughtfully stocked. Kitchen stock was great.Lots of coffees, teas, bottled water…all very thoughtful touches. Comfy beds. Beautiful little home. Pond was really nice. Convenient to Monandock. Really loved it. Lots of appreciation for the hosts."
United States
Len S.
The price is AU$420
includes taxes & fees
14 Oct - 15 Oct
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 AU$542
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 AU$674
includes taxes & fees
27 Oct - 28 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)
The price is AU$336
includes taxes & fees
1 Nov - 2 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 AU$376
includes taxes & fees
20 Oct - 21 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 AU$311
includes taxes & fees
8 Nov - 9 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)
The price is AU$552
includes taxes & fees
13 Oct - 14 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
The price is AU$599
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 AU$227
includes taxes & fees
20 Oct - 21 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 AU$969
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 AU$1,089
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 AU$932
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

The Putney Inn

The Putney Inn

8/10 Good
"The Putney Inn served its purpose. The place is quiet, very close to I-91, and well maintained. Putney is a cute little New England town, but restaurants are very limited. The rooms were fine, breakfast was basic but adequate, and overall, we had a good stay."
Daryl 1-night trip
Posted 14 hours ago
The Putney Inn

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
175
Accommodation
132 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$1,089