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

Search and Rent Winchester Condos

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A two-story house with a red door, green shutters, and a snow-covered front yard.

1. Centennial House

Centennial House
3.5 star property
Northfield
9.8 out of 10, Exceptional, (193 reviews)
"Excellent host making us feel very welcome. Very nice room and really lovely breakfast. Would certainly stay again if we are in the area."
United Kingdom
Alan
$174 nightly
The price is $183
Nov 8 - Nov 9
Total with taxes and fees
Centennial House
A windmill, a row of cabins, and a grassy field at night.

2. Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.2 out of 10, Wonderful, (82 reviews)
"Clean rooms, comfortable beds, smooth remote check-in with door code, showerhead was great and the barn door into the bathroom was a unique use of space. We enjoyed our stay."
United States
Donna
$96 nightly
The price is $107
Nov 16 - Nov 17
Total with taxes and fees
Windmill Motel Restaurant
The exterior of Latchis Hotel with a classic architectural style, large windows, and a prominent entrance.

3. Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (1,001 reviews)
"Hotel was great with extremely helpful, engaging and friendly staff."
United States
Erik
$115 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
Latchis Hotel
A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

4. The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.4 out of 10, Exceptional, (423 reviews)
"Easy check in and nice spot for traveling around the area."
United States
Al
$133 nightly
The price is $149
Nov 22 - Nov 23
Total with taxes and fees
The Inn At Crumpin Fox
A stone fire pit with flames in front of a house with a covered porch and blue lighting.

5. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,002 reviews)
"Stayed one night. Staff was very friendly. Clean rooms, easy parking, nice breakfast."
United States
Timothy
$139 nightly
The price is $153
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

6. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (899 reviews)
"Very nice staff and enjoyed my stay."
United States
Charlene
$112 nightly
The price is $124
Nov 15 - Nov 16
Total with taxes and fees
Comfort Inn & Suites Brattleboro I-91
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

7. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Excellent stay"
United States
Lisa
$134 nightly
The price is $145
Nov 8 - Nov 9
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

8. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,001 reviews)
"Great place to go"
United States
Ruddy
$142 nightly
The price is $154
Nov 9 - Nov 10
Total with taxes and fees
Best Western Plus Keene Hotel
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

9. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (431 reviews)
"Comfortable, clean, friendly staff, great breakfast"
United States
Dayle
$154 nightly
The price is $167
Nov 28 - Nov 29
Total with taxes and fees
Hampton Inn & Suites Keene
A hotel room with two beds, a TV, a desk, and a window with curtains.

10. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,000 reviews)
"convenient and safe place to stay while on a drivng vacation through New England"
United States
CHERYL
$97 nightly
The price is $105
Nov 9 - Nov 10
Total with taxes and fees
Days Inn by Wyndham Keene NH
A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

11. Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,001 reviews)
"Room was very clean and check in was excellent"
United States
Faith
$115 nightly
The price is $126
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn Brattleboro
A dock extending into a lake with a grassy area in the foreground and trees in the background.

12. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (707 reviews)
"Loved view of the river"
United States
Steve
$141 nightly
The price is $153
Dec 6 - Dec 7
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel
A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.

13. The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.2 out of 10, Good, (1,001 reviews)
"Good location. About what one might expect in a budget motel."
United States
Rick
$130 nightly
The price is $143
Dec 6 - Dec 7
Total with taxes and fees
The Covered Bridge Inn
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

14. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (699 reviews)
"I asked him on the front desk if I get a coffee machine but hi said no wen i order online they said breakfast is available but is not the guy in front desk was rude"
United States
Luis
$99 nightly
The price is $109
Dec 6 - Dec 7
Total with taxes and fees
Econo Lodge Brattleboro South
A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

15. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
$143 nightly
The price is $155
Nov 17 - Nov 18
Total with taxes and fees
The Carriage Barn Inn
A hotel with a clock tower, a parking lot, and a well-maintained garden.

16. Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.6 out of 10, Good, (531 reviews)
"The front desk were very helpful"
United States
Ron
$103 nightly
The price is $113
Nov 8 - Nov 9
Total with taxes and fees
Black Mountain Inn
A historic brick building with a porch and a sign reading "Burrell House."

17. The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (189 reviews)
"The Burrell House is a lovely historic home convenient to downtown Keene. The room was very clean and the bed super comfortable. There is no staff but it worked fine for my stay."
United States
Carol
$153 nightly
The price is $166
Nov 16 - Nov 17
Total with taxes and fees
The Burrell House
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

18. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$149 nightly
The price is $161
Nov 11 - Nov 12
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.

19. Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (258 reviews)
"Great place to stay."
United States
Cecil
$223 nightly
The price is $243
Nov 8 - Nov 9
Total with taxes and fees
Vikings Villages Resort
A cozy living room with a fireplace, a coffee station, and a view of the outside.

20. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.4 out of 10, (114 reviews)
"Value for money. Clean and conveniently located. Friendly staff."
United States
Swaraj
$95 nightly
The price is $105
Nov 8 - Nov 9
Total with taxes and fees
Colonial Motel
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

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

10/10 Excellent
"amazing place, genuinely kind and helpful staff."
Samantha 2-night trip
Posted 6 hours ago
Travelodge by Wyndham Brattleboro VT

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
3,319
Accommodation
0 Condo Rentals
Lowest Price
$105
Highest Price
$243

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