Hotels in Winchester
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Aug 17 - Aug 18Tomorrow
Aug 18 - Aug 19This weekend
Aug 21 - Aug 23Next weekend
Aug 28 - Aug 30Where to stay in Winchester?
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – AmherstSouth Deerfield
$99
$110 total
includes taxes & fees
Aug 23 - Aug 24
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection HotelKeene
$120
$130 total
includes taxes & fees
Sep 1 - Sep 2
Comfort Inn & Suites Hadley - Amherst
Comfort Inn & Suites Hadley - AmherstHadley
$144
$160 total
includes taxes & fees
Sep 7 - Sep 8
Inn on Boltwood
Inn on BoltwoodAmherst
$169
$189 total
includes taxes & fees
Aug 18 - Aug 19
Windmill Motel Restaurant
Windmill Motel RestaurantBernardston
$122
$136 total
includes taxes & fees
Aug 18 - Aug 19
The Colonial Hotel
The Colonial HotelGardner
$170
$190 total
includes taxes & fees
Aug 19 - Aug 20
Best Western Plus Keene Hotel
Best Western Plus Keene HotelKeene
$149
$162 total
includes taxes & fees
Aug 18 - Aug 19
Vikings Villages Resort
Vikings Villages ResortGuilford
$170
$199 total
includes taxes & fees
Sep 14 - Sep 15
River Valley Inn
River Valley InnWest Hatfield
$93
$103 total
includes taxes & fees
Sep 6 - Sep 7
Latchis Hotel
Latchis HotelBrattleboro
$112
$124 total
includes taxes & fees
Aug 19 - Aug 20
Hampton Inn Brattleboro
Hampton Inn BrattleboroBrattleboro
$117
$129 total
includes taxes & fees
Sep 8 - Sep 9
Colonial Motel
Colonial MotelBrattleboro
$77
$84 total
includes taxes & fees
Aug 18 - Aug 19
The Inn At Crumpin Fox
The Inn At Crumpin FoxBernardston
$162
$181 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Hadley Amherst
Courtyard by Marriott Hadley AmherstHadley
$161
$180 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91Brattleboro
$135
$148 total
includes taxes & fees
Sep 13 - Sep 14
Homewood Suites by Hilton Hadley Amherst
Homewood Suites by Hilton Hadley AmherstHadley
$155
$173 total
includes taxes & fees
Sep 7 - Sep 8
The Putney Inn
The Putney InnPutney
$121
$133 total
includes taxes & fees
Aug 18 - Aug 19
Black Walnut Inn
Black Walnut InnNorth Amherst
$175
$196 total
includes taxes & fees
Aug 18 - Aug 19
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection HotelWest Chesterfield
$152
$165 total
includes taxes & fees
Sep 6 - Sep 7
Go beyond your typical stay in Winchester
Pet friendly
Family friendly
Cottage
Top landmarks in Winchester
Cass Pond
Cass Pond is 0.7 mi (1.2 km) from central Richmond, why not stop by during your stay.
Winchester Speedpark
Wanna race? You could pay a visit to Winchester Speedpark located 2.6 mi (4.2 km) from central Winchester.
Richmond Wildlife Manangement Area
Richmond Wildlife Manangement Area is 1.6 mi (2.6 km) from central Richmond, why not stop by during your stay. Want to stretch your legs some more? Head to Barden State Wildlife Management Area, just a short walk away.
New England Sweetwater Farm & Distillery
New England Sweetwater Farm & Distillery is in the heart of Winchester, so why not stop by during your stay.
Barden State Wildlife Management Area
Barden State Wildlife Management Area is 1.5 mi (2.4 km) from central Richmond, why not stop by during your stay. Want to stretch your legs some more? Head to Richmond Wildlife Manangement Area, just a short walk away.
Conant Public Library
Conant Public Library is worth a visit when in central Winchester.
Bennett Gorge
Bennett Gorge is 2.7 mi (4.4 km) from central Richmond, why not stop by during your stay.
Richmond Town Hall
Richmond Town Hall is worth a visit, located 0.6 mi (0.9 km) from central Richmond.
Learn more about Winchester
Winchester is well-known for its attractions such as Winchester Speedpark and Pisgah State Park. The city has something for everyone including sights like Cass Pond and New England Sweetwater Farm & Distillery within a scenic setting.
See all hotels in Winchester
Check out reviews of Winchester hotels guests love
Hampton Inn & Suites Greenfield
8/10 Good
"Friendly staff, clean lobby and adequate rooms."
Hampton Inn Brattleboro
10/10 Excellent
"The room was very clean. The staff was very helpful. The breakfast was very nice. This was a one night stay returning from further North."
Days Inn by Wyndham Keene NH
8/10 Good
"It was a very pleasant stay"
Holiday Inn Express Hotel & Suites Brattleboro by IHG
8/10 Good
"Clean room, very nice front desk staff. Breakfast was good - nice variety and the coffee machine delivered great fresh coffee. It was worth paying the extra cost for this hotel vs the others in the area that seemed a bit sketchy."
The Putney Inn
10/10 Excellent
"Clean room, staff, breakfast, and parking were great!"
Riverside Hotel, an Ascend Collection Hotel
10/10 Excellent
"Huge room with a very comfy king bed and an incredible view of the Connecticut review. A five minute drive to Brattleboro Vermont."
Vikings Villages Resort
10/10 Excellent
"This resort was amazing! We booked the stay on our way back home from an event in New York. The cabin was comfortable and the property scenic. We wish we had the chance to stay longer, but will definitely be back. The Viking theme was incredible and the attention to detail in our cabin demonstrated the owners knowledge of what travelers need and want. We could not have been happier with our stay. This was more than just a place to sleep as it left us with a lot of good memories."
The Colonial Hotel
10/10 Excellent
"Everything was great! Mary is an awesome bartender!!! We live in FL now and when we come back to visit we stay here!"
Comfort Inn & Suites Brattleboro I-91
10/10 Excellent
"The front desk staff were friendly and engaged, the room was clean. That’s all we needed."