Hotels in Winchester

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Check prices for these dates

Tonight
May 1 - May 2
Tomorrow
May 2 - May 3
This weekend
May 1 - May 3
Next weekend
May 8 - May 10

Where to stay in Winchester?

Terrace/patio
The Maguire House Bed & Breakfast
The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 reviews)
Surrounded by Ashburnham's natural beauty, this cozy B&B offers rowing, cross-country skiing, and sledding on-site. Enjoy complimentary full breakfast daily and explore nearby attractions. The garden terrace and snack bar enhance your peaceful countryside retreat.
The price is $285
$285 total
includes taxes & fees
May 7 - May 8
The Maguire House Bed & Breakfast
Interior
The Colonial Hotel
The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,001 reviews)
Discover a peaceful retreat with Swedish spa services and a welcoming bar. Near Wachusett Mountain Ski Area, this countryside haven offers in-room refrigerators and convenient access to scenic Dunn State Park. Guests rave about the restaurant and attentive staff.
The price is $160
$179 total
includes taxes & fees
May 3 - May 4
The Colonial Hotel
Exterior
Gardner Inn
Gardner Inn
2.0 star property
Gardner
6.0 out of 10, (28 reviews)
Set near Dunn State Park, this hotel offers free WiFi and parking for hassle-free exploration. A 24-hour front desk ensures support at any hour, while the Old Mill Gift Shop provides local shopping opportunities just minutes away.
The price is $89
$100 total
includes taxes & fees
May 3 - May 4
Gardner Inn
BBQ/picnic area
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.2 out of 10, Wonderful, (460 reviews)
The price is $169
$194 total
includes taxes & fees
May 3 - May 4
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior
Monadnock Inn
Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (281 reviews)
Feel the enchantment at this mountain B&B adjacent to Shattuck Golf Course. Explore nearby hiking trails and mountain biking routes, then unwind in this historic inn. Free WiFi and parking add convenience while Jaffrey Civic Center offers cultural intrigue.
The price is $183
$198 total
includes taxes & fees
May 10 - May 11
Monadnock Inn
Free daily continental breakfast
The Carriage Barn Inn
The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (171 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
May 3 - May 4
The Carriage Barn Inn
Lobby
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,001 reviews)
Located in downtown Keene, this Art Deco hotel offers an indoor pool and 24-hour fitness center. Grab a bite at the coffee shop or unwind with drinks at the bar. Near Colonial Theatre and Central Square, enjoy free WiFi and parking during your stay.
The price is $180
$195 total
includes taxes & fees
May 31 - Jun 1
Courtyard by Marriott Keene Downtown
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, (771 reviews)
The price is $180
$195 total
includes taxes & fees
May 7 - May 8
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior
The Burrell House
The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (163 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 3 - May 4
The Burrell House
Restaurant
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,002 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 3 - May 4
Best Western Plus Keene Hotel
Free daily buffet breakfast
Hampton Inn & Suites Keene
Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (382 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 $176
$191 total
includes taxes & fees
May 27 - May 28
Hampton Inn & Suites Keene
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, (1,001 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
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, (1,000 reviews)
The price is $97
$105 total
includes taxes & fees
May 4 - May 5
Days Inn by Wyndham Keene NH
Free daily full breakfast
Centennial House
Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (174 reviews)
Wake up to a full breakfast at this historic Northfield B&B adjacent to golf facilities. Explore nearby hiking trails or enjoy cross-country skiing, then relax in the garden or terrace. Free WiFi and parking complement your stay near Dickinson Memorial Library.
The price is $179
$190 total
includes taxes & fees
May 5 - May 6
Centennial House
Lobby sitting area
Inn at Valley Farms
Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (17 reviews)
Unwind in this welcoming inn with complimentary WiFi and parking, surrounded by garden scenery. Just minutes from Hooper Golf Course and Club, this countryside retreat offers a perfect base for exploring local attractions near Springfield and Bellows Falls.
The price is $164
$178 total
includes taxes & fees
May 3 - May 4
Inn at Valley Farms
Exterior
The Inn At Crumpin Fox
The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (359 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 $184
$206 total
includes taxes & fees
May 14 - May 15
The Inn At Crumpin Fox
Front of property - evening/night
Chesterfield Inn
Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
Tucked away in West Chesterfield, this charming B&B offers complimentary breakfast, WiFi, and parking. Unwind with a massage, sip drinks at the bar, or explore the garden and terrace before visiting nearby Actors Theatre Playhouse.
The price is $301
$327 total
includes taxes & fees
May 3 - May 4
Chesterfield Inn
Pool
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (909 reviews)
The price is $155
$173 total
includes taxes & fees
May 10 - May 11
Hampton Inn & Suites Greenfield
Exterior
The Putney Inn
The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,000 reviews)
The price is $105
$115 total
includes taxes & fees
May 3 - May 4
The Putney Inn
Exterior
Latchis Hotel
Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (872 reviews)
The price is $130
$143 total
includes taxes & fees
May 3 - May 4
Latchis Hotel
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.
See properties

Learn more about Winchester

Winchester is well-known for its attractions such as Rhododendron State Park and Winchester Speedpark. The city has something for everyone including sights like Birch Point and Pisgah State Park within a scenic setting.

See all hotels in Winchester
Winchester, New Hampshire in winter

Check out reviews of Winchester hotels guests love

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Great breakfast and comfortable bed"
Brian 1-night trip
Posted 7 hours ago
Best Western Plus Keene Hotel

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.