Hotels in Winchester
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Centennial House
Centennial HouseNorthfield
9.6 out of 10, Exceptional, (173 reviews)
- Charming colonial B&B near golf course with hiking trails and complimentary breakfast.
The price is $179
$190 total
includes taxes & fees
Feb 1 - Feb 2
The Inn At Crumpin Fox
The Inn At Crumpin FoxBernardston
9.2 out of 10, Wonderful, (352 reviews)
- Wake up to rolling hills and adventure at this charming Bernardston inn.
The price is $127
$142 total
includes taxes & fees
Feb 13 - Feb 14
Econo Lodge Brattleboro South
Econo Lodge Brattleboro SouthBrattleboro
5.4 out of 10, (616 reviews)
- Quiet riverside motel with free breakfast and WiFi, near downtown Brattleboro.
The price is $67
$74 total
includes taxes & fees
Mar 1 - Mar 2
The One Cat B&B
The One Cat B&BBrattleboro
9.6 out of 10, Exceptional, (78 reviews)
- Charming B&B with full breakfast near Brattleboro Station, trails, and museums.
The price is $150
$165 total
includes taxes & fees
Feb 1 - Feb 2
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NHKeene
7.0 out of 10, Good, (1,000 reviews)
The price is $81
$88 total
includes taxes & fees
Feb 1 - Feb 2
Latchis Hotel
Latchis HotelBrattleboro
8.4 out of 10, Very Good, (844 reviews)
The price is $124
$137 total
includes taxes & fees
Mar 1 - Mar 2
The Covered Bridge Inn
The Covered Bridge InnBrattleboro
7.6 out of 10, Good, (1,001 reviews)
- Quaint Vermont escape near hiking trails with free daily breakfast and parking.
The price is $108
$119 total
includes taxes & fees
Jan 31 - Feb 1
Vikings Villages Resort
Vikings Villages ResortGuilford
10.0 out of 10, Exceptional, (159 reviews)
- Rustic lodge with rooftop views near Sweet Pond State Park in Vermont.
The price is $132
$155 total
includes taxes & fees
Feb 1 - Feb 2
Best Western Plus Keene Hotel
Best Western Plus Keene HotelKeene
8.4 out of 10, Very Good, (1,001 reviews)
- Stay in a peaceful Keene hotel with convenient access to Ashuelot River.
The price is $139
$151 total
includes taxes & fees
Feb 1 - Feb 2
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection HotelKeene
8.4 out of 10, Very Good, (979 reviews)
- Historic charm and inviting indoor pool await in downtown Keene.
The price is $119
$129 total
includes taxes & fees
Feb 1 - Feb 2
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91Brattleboro
8.6 out of 10, Excellent, (759 reviews)
- Convenient hotel near I-91, offering a restaurant and free amenities for travelers.
The price is $116
$127 total
includes taxes & fees
Mar 1 - Mar 2
Inn on Putney Road
Inn on Putney RoadBrattleboro
9.8 out of 10, Exceptional, (56 reviews)
- Take a scenic stroll through gardens to downtown from this riverside B&B.
The price is $235
$258 total
includes taxes & fees
Feb 1 - Feb 2
Hampton Inn Brattleboro
Hampton Inn BrattleboroBrattleboro
8.2 out of 10, Very Good, (940 reviews)
- Riverside comfort with fitness center and hot tub near United States Navy Seabee Bridge.
The price is $105
$116 total
includes taxes & fees
Mar 2 - Mar 3
Hampton Inn & Suites Keene
Hampton Inn & Suites KeeneKeene
8.8 out of 10, Excellent, (364 reviews)
- Experience serene New England comfort with a convenient location near Ashuelot River.
The price is $169
$184 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHGBrattleboro
8.8 out of 10, Excellent, (1,000 reviews)
- Brattleboro retreat with indoor pool and proximity to local attractions.
The price is $148
$163 total
includes taxes & fees
Feb 1 - Feb 2
The Carriage Barn Inn
The Carriage Barn InnKeene
9.6 out of 10, Exceptional, (167 reviews)
- Historic B&B in charming Keene offers complimentary breakfast and art gallery access.
The price is $152
$165 total
includes taxes & fees
Feb 13 - Feb 14
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection HotelWest Chesterfield
9.6 out of 10, Exceptional, (636 reviews)
The price is $142
$155 total
includes taxes & fees
Mar 1 - Mar 2
Colonial Motel And Spa
Colonial Motel And SpaBrattleboro
6.8 out of 10, (1,002 reviews)
- Relaxing Vermont retreat with spa services and two inviting indoor pools.
The price is $115
$126 total
includes taxes & fees
Feb 27 - Feb 28
Black Mountain Inn
Black Mountain InnBrattleboro
7.4 out of 10, Good, (480 reviews)
- Serene Black Mountain retreat with outdoor pool and peaceful hiking trails nearby.
The price is $127
$139 total
includes taxes & fees
Feb 1 - Feb 2
Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VTBrattleboro
6.0 out of 10, (746 reviews)
- Perfect Vermont location for skiing and outdoor activities year-round.
The price is $71
$78 total
includes taxes & fees
Feb 1 - Feb 2
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.
Go beyond your typical stay in Winchester
Pet friendly
Top landmarks in Winchester
Learn more about Winchester
Winchester is well-known for its attractions such as New England Sweetwater Farm & Distillery and Bennett Gorge. The city has something for everyone including sights like Pisgah State Park and Barden State Wildlife Management Area within a scenic setting.
Check out reviews of Winchester hotels guests love
The Colonial Hotel
10/10 Excellent
