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Hotels in Winchester
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Where to stay in Winchester?
Centennial House
Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173)
9.6/10
Exceptional
(173)
The price is $190
$190
$201 total
includes taxes & fees
Feb 1 - Feb 2
The One Cat B&B
The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
9.6/10
Exceptional
(78)
The price is $135
$135
$149 total
includes taxes & fees
Jan 12 - Jan 13
Latchis Hotel
Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (843)
8.4/10
Very Good
(843)
The price is $131
$131
$144 total
includes taxes & fees
Jan 8 - Jan 9
Econo Lodge Brattleboro South
Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.4 out of 10, (609)
5.4/10
(609)
The price is $64
$64
$70 total
includes taxes & fees
Jan 14 - Jan 15
The Inn At Crumpin Fox
The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (348)
9.2/10
Wonderful
(348)
The price is $130
$130
$146 total
includes taxes & fees
Jan 21 - Jan 22
Inn on Putney Road
Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
9.8/10
Exceptional
(56)
The price is $235
$235
$258 total
includes taxes & fees
Jan 8 - Jan 9
The Covered Bridge Inn
The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1000)
7.6/10
Good
(1000)
The price is $84
$84
$93 total
includes taxes & fees
Jan 11 - Jan 12
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very Good, (975)
8.4/10
Very Good
(975)
The price is $120
$120
$130 total
includes taxes & fees
Jan 8 - Jan 9
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1000)
8.4/10
Very Good
(1000)
The price is $139
$139
$151 total
includes taxes & fees
Jan 8 - Jan 9
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1006)
8.8/10
Excellent
(1006)
The price is $144
$144
$158 total
includes taxes & fees
Jan 11 - Jan 12
Colonial Motel And Spa
Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1002)
6.8/10
(1002)
The price is $140
$140
$154 total
includes taxes & fees
Jan 8 - Jan 9
Hampton Inn & Suites Keene
Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (362)
8.8/10
Excellent
(362)
The price is $173
$173
$188 total
includes taxes & fees
Feb 1 - Feb 2
Black Mountain Inn
Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (477)
7.4/10
Good
(477)
The price is $110
$110
$121 total
includes taxes & fees
Jan 11 - Jan 12
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (756)
8.6/10
Excellent
(756)
The price is $138
$138
$152 total
includes taxes & fees
Jan 11 - Jan 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, (634)
9.6/10
Exceptional
(634)
The price is $152
$152
$165 total
includes taxes & fees
Feb 5 - Feb 6
Days Inn by Wyndham Keene NH
Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1001)
7.0/10
Good
(1001)
The price is $81
$81
$88 total
includes taxes & fees
Jan 10 - Jan 11
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (932)
8.2/10
Very Good
(932)
The price is $147
$147
$161 total
includes taxes & fees
Jan 19 - Jan 20
Chesterfield Inn
Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
9.0/10
Wonderful
(104)
The price is $307
$307
$334 total
includes taxes & fees
Jan 13 - Jan 14
Travelodge by Wyndham Brattleboro VT
Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (738)
6.0/10
(738)
The price is $71
$71
$78 total
includes taxes & fees
Jan 11 - Jan 12
Vikings Villages Resort
Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (156)
10/10
Exceptional
(156)
The price is $208
$208
$243 total
includes taxes & fees
Jan 8 - Jan 9
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.
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.
Budget hotels in Winchester and vicinity
8.4 out of 10, Very Good, (1000)
8.4/10
Very Good
(1000)
The price is $94
$94
$103 total
includes taxes & fees
Jan 8 - Jan 9
7.0 out of 10, Good, (1001)
7.0/10
Good
(1001)
The price is $81
$81
$88 total
includes taxes & fees
Jan 10 - Jan 11
7.6 out of 10, Good, (1000)
7.6/10
Good
(1000)
The price is $84
$84
$93 total
includes taxes & fees
Jan 11 - Jan 12
9.2 out of 10, Wonderful, (126)
9.2/10
Wonderful
(126)
The price is $90
$90
$150 total
includes taxes & fees
Jan 11 - Jan 12
7.4 out of 10, Good, (477)
7.4/10
Good
(477)
The price is $110
$110
$121 total
includes taxes & fees
Jan 11 - Jan 12
8.4 out of 10, Very Good, (843)
8.4/10
Very Good
(843)
The price is $131
$131
$144 total
includes taxes & fees
Jan 8 - Jan 9
9.6 out of 10, Exceptional, (78)
9.6/10
Exceptional
(78)
The price is $135
$135
$149 total
includes taxes & fees
Jan 12 - Jan 13
9.8 out of 10, Exceptional, (18)
9.8/10
Exceptional
(18)
The price is $129
$129
$141 total
includes taxes & fees
Jan 11 - Jan 12
9.6 out of 10, Exceptional, (166)
9.6/10
Exceptional
(166)
The price is $127
$127
$138 total
includes taxes & fees
Jan 21 - Jan 22
9.6 out of 10, Exceptional, (156)
9.6/10
Exceptional
(156)
The price is $161
$161
$179 total
includes taxes & fees
Jan 8 - Jan 9
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel2.5 star property
Keene
8.4 out of 10, Very Good, (975)
8.4/10
Very Good
(975)
The price is $120
$120
$130 total
includes taxes & fees
Jan 8 - Jan 9
8.4 out of 10, Very Good, (1000)
8.4/10
Very Good
(1000)
The price is $139
$139
$151 total
includes taxes & fees
Jan 8 - Jan 9
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-912.5 star property
Brattleboro
8.6 out of 10, Excellent, (756)
8.6/10
Excellent
(756)
The price is $138
$138
$152 total
includes taxes & fees
Jan 11 - Jan 12
9.2 out of 10, Wonderful, (348)
9.2/10
Wonderful
(348)
The price is $130
$130
$146 total
includes taxes & fees
Jan 21 - Jan 22
9.8 out of 10, Exceptional, (342)
9.8/10
Exceptional
(342)
The price is $158
$158
$173 total
includes taxes & fees
Jan 8 - Jan 9
8.2 out of 10, Very Good, (932)
8.2/10
Very Good
(932)
The price is $147
$147
$161 total
includes taxes & fees
Jan 19 - Jan 20
7.6 out of 10, Good, (277)
7.6/10
Good
(277)
The price is $148
$148
$161 total
includes taxes & fees
Jan 8 - Jan 9
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (634)
9.6/10
Exceptional
(634)
The price is $152
$152
$165 total
includes taxes & fees
Feb 5 - Feb 6
10.0 out of 10, Exceptional, (14)
10/10
Exceptional
(14)
The price is $161
$161
$174 total
includes taxes & fees
Jan 11 - Jan 12
8.8 out of 10, Excellent, (1005)
8.8/10
Excellent
(1005)
The price is $160
$160
$179 total
includes taxes & fees
Jan 11 - Jan 12
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.
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
Apartment
Family friendly
Cottage
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 Cass Pond within a scenic setting.
Check out reviews of Winchester hotels guests love
Holiday Inn Express Hotel & Suites Brattleboro by IHG
10/10 Excellent
"Clean. Friendly staff. Corn Chowder in the lobby!"
Riverhouse by Weekender (Formerly Jack Daniels Inn)
10/10 Excellent
"Beds were sooo comfortable "
Comfort Inn & Suites Brattleboro I-91
10/10 Excellent
"The room was clean and the staff was wonderful"
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
"The lady never fixed the pancake bag so no pancakes sad"
Latchis Hotel
10/10 Excellent
"Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!"
Hampton Inn & Suites Greenfield
10/10 Excellent
"very quiet"
Hampton Inn Brattleboro
10/10 Excellent
"Good breakfast, great staff and very good location "
Colonial Motel And Spa
10/10 Excellent
"Great location and service
"
Four Columns Inn
10/10 Excellent
"Everything was great 👍 I will stay there again and highly recommend to others "
Frequently asked questions
Can I book refundable hotels in Winchester?
If you need the flexibility to change your travel plans to Winchester, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
What will the weather in Winchester be like during my vacation?
July and August are typically the warmest months in Winchester when the average temp is 67°F. January and February are the coldest months when the average temperature is 28°F. October and July are the months with the most rain.
Why should I book my Winchester hotel through Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.