Hotels in Winchester

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This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

Where to stay in Winchester?

Superior Single Room, 1 Queen Bed | Iron/ironing board, free WiFi

Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
9.4 out of 10, Exceptional, (3 reviews)
The price is $247
$304 total
includes taxes & fees
Jun 30 - Jul 1
Deerfield Inn
Lobby

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, (1,006 reviews)
Escape to this welcoming hotel in Keene, where you'll find an indoor pool and fitness center near local shops and eateries. Despite its commercial location, guests enjoy a quiet atmosphere, free breakfast, and helpful staff to enhance your stay.
The price is $109
$118 total
includes taxes & fees
Jun 30 - Jul 1
Keene Elm City Hotel, an Ascend Collection Hotel
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,006 reviews)
Quiet rooms welcome travelers to this restful retreat near the Ashuelot River and Thorne Sagendorph Art Gallery. The restaurant and bar provide delicious meals, while fellow guests rave about the free breakfast and helpful staff.
The price is $127
$138 total
includes taxes & fees
Jul 1 - Jul 2
Best Western Plus Keene Hotel
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (822 reviews)
Warm Brattleboro accommodations with complimentary breakfast, WiFi, and parking just minutes from United States Navy Seabee Bridge. Energize at the fitness center after exploring nearby attractions. Fellow travelers consistently praise the exceptionally helpful staff.
The price is $113
$124 total
includes taxes & fees
Jul 2 - Jul 3
Comfort Inn & Suites Brattleboro I-91
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
Tucked into walkable Keene, this cozy guesthouse offers free WiFi and convenient self parking. Explore nearby Central Square and local shops, then unwind in the peaceful picnic area after a day of adventures.
The price is $147
$164 total
includes taxes & fees
Jun 30 - Jul 1
The Burrell House
Deluxe Double Room, 1 Queen Bed, Valley View | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
8.8 out of 10, Excellent, (22 reviews)
The price is $135
$151 total
includes taxes & fees
Jun 30 - Jul 1
Windmill Motel Restaurant
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
Surrounded by winter adventures, this charming B&B offers free local cuisine breakfast, WiFi, and parking. Nearby Southern Vermont Natural History Museum and Hogback Mountain Conservation Area provide natural escapes, while the helpful staff ensures a memorable stay.
The price is $158
$173 total
includes taxes & fees
Jun 30 - Jul 1
Colonel Williams Inn
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (371 reviews)
Nestled in Bernardston with nearby hiking trails, kayaking, and mountain biking opportunities, this welcoming inn offers free WiFi and parking. Close to Cushman Library and Powers Institute Museum, guests consistently praise the helpful staff and clean rooms.
The price is $162
$181 total
includes taxes & fees
Jul 12 - Jul 13
The Inn At Crumpin Fox
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,002 reviews)
Immerse yourself in Brattleboro charm at this welcoming hotel with complimentary breakfast and parking. Unwind in the hot tub, energize at the fitness center, or grab a coffee at the café while exploring nearby attractions like Brattleboro Bowl.
The price is $122
$134 total
includes taxes & fees
Jul 5 - Jul 6
Hampton Inn Brattleboro
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
Wake up to continental breakfast at this cozy Keene B&B, located near the Thorne-Sagendorph Art Gallery. Enjoy free WiFi and parking while exploring the area, with Manchester-Boston Regional Airport and Brattleboro Station both accessible for day trips.
The price is $177
$192 total
includes taxes & fees
Jun 30 - Jul 1
The Carriage Barn Inn
In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,003 reviews)
The price is $88
$96 total
includes taxes & fees
Jul 6 - Jul 7
Days Inn by Wyndham Keene NH
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (914 reviews)
The price is $112
$123 total
includes taxes & fees
Jul 5 - Jul 6
Latchis Hotel
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (140 reviews)
Immerse yourself in the tranquility of Shelburne Falls at this welcoming guesthouse. Free WiFi and daily housekeeping provide essential comforts, while snowmobiling, snowshoeing, and sledding await right outside. Popular attractions like Glacial Potholes are nearby.
The price is $104
$166 total
includes taxes & fees
Jun 30 - Jul 1
Blooming Inn
Front of property

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (199 reviews)
Enjoy mountain adventures from this secluded retreat with free WiFi and parking. Kayak, bike, or snowshoe directly from the property. Helpful staff ensure a memorable stay near Shattuck Brook Wildlife Management Area.
The price is $172
$201 total
includes taxes & fees
Jul 26 - Jul 27
Vikings Villages Resort
Lobby

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, (1,000 reviews)
Splash into the indoor pool at this welcoming Brattleboro hotel near United States Navy Seabee Bridge. Free breakfast, WiFi and parking enhance your stay while the 24-hour fitness center keeps routines on track. Guests consistently praise the helpful staff.
The price is $134
$147 total
includes taxes & fees
Jul 2 - Jul 3
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Front of property

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (495 reviews)
This tranquil inn offers a seasonal outdoor pool surrounded by nature's calm. Nearby hiking and mountain biking trails await adventurous guests. Free breakfast, WiFi, and parking enhance your Brattleboro stay, just minutes from local attractions.
The price is $145
$160 total
includes taxes & fees
Jun 30 - Jul 1
Black Mountain Inn
Exterior

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.2 out of 10, Wonderful, (74 reviews)
The price is $225
$248 total
includes taxes & fees
Jul 1 - Jul 2
The Inn At Quail Run
Sundeck

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (657 reviews)
The price is $152
$165 total
includes taxes & fees
Jul 5 - Jul 6
Riverside Hotel, an Ascend Collection Hotel
Pool

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (923 reviews)
The price is $155
$173 total
includes taxes & fees
Jul 12 - Jul 13
Hampton Inn & Suites Greenfield
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (44 reviews)
Escape to this cozy Newfane inn offering free breakfast, WiFi, and parking. The garden-view tavern serves delicious dinner, while nearby attractions like Moore Free Library and Rock River Preserve await exploration.
The price is $131
$142 total
includes taxes & fees
Jun 30 - Jul 1
Four Columns Inn
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 landmarks in Winchester

Winchester Speedpark

Wanna race? You could pay a visit to Winchester Speedpark located 2.6 mi (4.2 km) from central Winchester.
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Learn more about Winchester

Winchester is well-known for its attractions such as Winchester Speedpark and New England Sweetwater Farm & Distillery. The city has something for everyone including sights like Conant Public Library and Loring Field within a scenic setting.

See all hotels in Winchester
A snow-covered town with a river running through it, surrounded by mountains and trees.

Check out reviews of Winchester hotels guests love

The Putney Inn

The Putney Inn

10/10 Excellent
"The location is ideal for pursuing a huge variety of interests, and the rooms have all of the expected amenities and are clean and comfortable."
Russell 2-night trip
Posted 7 hours ago
The Putney Inn

Frequently asked questions

What hotels do travelers like in Winchester?
Guests like Windmill Motel Restaurant.
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 Keyâ„¢, our rewards program, you will be able to earn and use OneKeyCashâ„¢* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.