Hotels in Winchester

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Check prices for these dates

This weekend
May 22 - May 24
Next weekend
May 29 - May 31

Where to stay in Winchester?

Front of property

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.2 out of 10, Wonderful, (12 reviews)
The price is $135
$151 total
includes taxes & fees
May 20 - May 21
Windmill Motel Restaurant
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (80 reviews)
Wake up to a complimentary full breakfast at this cozy cat-themed B&B. Just a 5-minute walk from Brattleboro Station with nearby hiking trails, kayaking, and mountain biking. New England Youth Theatre and Brattleboro Museum & Art Center wait to be explored.
The price is $250
$275 total
includes taxes & fees
May 21 - May 22
The One Cat B&B
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (364 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 $166
$185 total
includes taxes & fees
Jun 1 - Jun 2
The Inn At Crumpin Fox
Seasonal outdoor pool

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (637 reviews)
Escape to this comfortable Brattleboro motel offering a seasonal outdoor pool, free breakfast, and WiFi. Just minutes from Vermont Marketplace and Estey Organ Museum, with winter sports nearby and convenient train station access.
The price is $71
$78 total
includes taxes & fees
May 25 - May 26
Econo Lodge Brattleboro South
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (883 reviews)
The price is $143
$157 total
includes taxes & fees
May 25 - May 26
Latchis Hotel
Deluxe Chalet | Exterior

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (194 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 $150
$175 total
includes taxes & fees
Jun 1 - Jun 2
Vikings Villages Resort
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,007 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 $154
$167 total
includes taxes & fees
May 20 - May 21
Best Western Plus Keene Hotel
Exterior

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, (1,004 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 $140
$152 total
includes taxes & fees
May 26 - May 27
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,001 reviews)
The price is $105
$113 total
includes taxes & fees
May 31 - Jun 1
Days Inn by Wyndham Keene NH
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (806 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 $138
$152 total
includes taxes & fees
May 26 - May 27
Comfort Inn & Suites Brattleboro I-91
Free breakfast

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (978 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
Jun 7 - Jun 8
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, (172 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 1 - Jun 2
The Carriage Barn Inn
Front of property

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (491 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 $133
$146 total
includes taxes & fees
May 20 - May 21
Black Mountain Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
Overlooking the West River, this charming B&B offers lush gardens and a cozy bar/lounge. Just a 15-minute walk from Brattleboro Station and near local attractions. Enjoy free breakfast, WiFi, and parking, plus relaxing deep-tissue massages.
The price is $284
$312 total
includes taxes & fees
May 20 - May 21
Inn on Putney Road
Free daily continental breakfast

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,002 reviews)
Tucked into scenic Brattleboro, this inn welcomes outdoor enthusiasts with nearby hiking, snowboarding, and sledding options. Start each day with complimentary continental breakfast before exploring local attractions like the Brattleboro Bowl just minutes away.
The price is $81
$89 total
includes taxes & fees
May 20 - May 21
The Covered Bridge Inn
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (166 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 $136
$151 total
includes taxes & fees
May 25 - May 26
The Burrell House
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, (650 reviews)
The price is $152
$165 total
includes taxes & fees
Jun 7 - Jun 8
Riverside Hotel, an Ascend Collection Hotel
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (775 reviews)
The price is $180
$195 total
includes taxes & fees
May 31 - Jun 1
Fairfield Inn & Suites by Marriott Keene Downtown
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, (1,003 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 $175
$193 total
includes taxes & fees
Jun 7 - Jun 8
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free daily buffet breakfast

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (385 reviews)
Located in Keene with easy access to Cheshire Children's Museum, this hotel offers a refreshing indoor pool and 24-hour fitness center. Enjoy complimentary breakfast, free parking, and attentive staff to enhance your stay while exploring nearby attractions.
The price is $196
$212 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn & Suites Keene
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 Pisgah State Park. The city has something for everyone including sights like New England Sweetwater Farm & Distillery and Rhododendron State Park within a scenic setting.

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Winchester, New Hampshire in winter

Check out reviews of Winchester hotels guests love

The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"The property was surrounded beautifully by trees with pleasant sitting areas in the inner courtyard. A cozy relaxed environment. The weekend breakfast was satisfactory with enough choices Staff were very helpful and pleasant. Eager to please"
ellen m 2-night trip
Posted 7 hours ago
The Inn At Crumpin Fox

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 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.