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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winchester holiday homes

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

1. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (62 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is NZ$337
includes taxes & fees
26 Aug - 27 Aug
Lovely 2nd Floor Apartment
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

2. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is NZ$541
includes taxes & fees
25 Aug - 26 Aug
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

3. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is NZ$748
includes taxes & fees
31 Aug - 1 Sept
Stunning Glass House nestled in the Vermont wilderness!
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 NZ$815
includes taxes & fees
31 Aug - 1 Sept
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A garden with purple flowers and a river in the background.

5. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is NZ$490
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
A hallway with wooden flooring, white walls, and a bed in the background.

6. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is NZ$592
includes taxes & fees
2 Sept - 3 Sept
Cozy private 2 bed apartment in Shelburne Falls
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 NZ$355
includes taxes & fees
25 Aug - 26 Aug
Private bed with En-suite bathroom Marigold Room
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

8. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (53 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is NZ$1,073
includes taxes & fees
25 Aug - 26 Aug
Spacious 5BR w/ Hot Tub & Games
A four-poster bed with a grey bedspread, a wooden nightstand with a lamp, a wooden dresser, and a chair.

9. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Walpole
10.0 out of 10, Exceptional, (6 reviews)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
The price is NZ$636
includes taxes & fees
3 Sept - 4 Sept
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

10. 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, (9 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 NZ$649
includes taxes & fees
25 Aug - 26 Aug
Enjoy your stay in an antique home in an antique toy museum!
Two Adirondack chairs and a fire pit in a grassy field with a forested hill in the background.

11. Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene
Walpole
The price is NZ$820
includes taxes & fees
31 Aug - 1 Sept
Large Farmhouse with expansive views, firepit 15 min north of Keene
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

12. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (52 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is NZ$1,212
includes taxes & fees
3 Sept - 4 Sept
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A kitchen with a brick fireplace, wooden cabinets, a central island with stools, and a large window with plants.

13. Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Dublin
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is NZ$1,185
includes taxes & fees
25 Aug - 26 Aug
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is NZ$1,190
includes taxes & fees
22 Sept - 23 Sept
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

Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 1 hour ago
Colonial Motel

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
303
Accommodation
126 Holiday Homes
Lowest Price
NZ$337
Highest Price
NZ$1,212