Hotels in Winchester

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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 CNY920
CNY1,027 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 CNY1,703
CNY1,874 total
includes taxes & fees
May 21 - May 22
The One Cat B&B
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 CNY1,935
CNY2,129 total
includes taxes & fees
May 19 - May 20
Inn on Putney Road
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (363 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 CNY1,131
CNY1,263 total
includes taxes & fees
May 19 - May 20
The Inn At Crumpin Fox
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,005 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 CNY1,049
CNY1,138 total
includes taxes & fees
May 19 - May 20
Best Western Plus Keene Hotel
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 CNY484
CNY533 total
includes taxes & fees
May 24 - May 25
Econo Lodge Brattleboro South
Deluxe Chalet | Exterior

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (193 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 CNY924
CNY1,077 total
includes taxes & fees
May 19 - May 20
Vikings Villages Resort
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 CNY631
CNY685 total
includes taxes & fees
May 21 - May 22
Days Inn by Wyndham Keene NH
Lobby

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 CNY2,052
CNY2,226 total
includes taxes & fees
May 20 - May 21
Chesterfield Inn
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 CNY1,192
CNY1,311 total
includes taxes & fees
Jun 7 - Jun 8
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free breakfast

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (976 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 CNY832
CNY916 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn Brattleboro
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 CNY954
CNY1,035 total
includes taxes & fees
May 26 - May 27
Keene Elm City Hotel, an Ascend Collection Hotel
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 CNY1,207
CNY1,309 total
includes taxes & fees
May 19 - May 20
The Carriage Barn Inn
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 CNY1,333
CNY1,447 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn & Suites Keene
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 CNY952
CNY1,047 total
includes taxes & fees
Jun 7 - Jun 8
Comfort Inn & Suites Brattleboro I-91
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 CNY905
CNY996 total
includes taxes & fees
May 19 - May 20
Black Mountain Inn
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (882 reviews)
The price is CNY975
CNY1,072 total
includes taxes & fees
May 25 - May 26
Latchis Hotel
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 CNY883
CNY971 total
includes taxes & fees
May 19 - May 20
The Covered Bridge Inn
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 CNY1,036
CNY1,124 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, (774 reviews)
The price is CNY1,223
CNY1,327 total
includes taxes & fees
May 31 - Jun 1
Fairfield Inn & Suites by Marriott Keene Downtown
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 Rhododendron State Park and New England Sweetwater Farm & Distillery within a scenic setting.

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Winchester, New Hampshire in winter

Check out reviews of Winchester hotels guests love

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

8/10 Good
"Location is great. Lots of things within walking distance. Basement suite had no natural light and the worst LED light bulbs. Try to get a different room if possible. Parking was free but not very convenient. I'd stay there again but would ask about which room I was getting."
Darrin 2-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott Keene Downtown

Frequently asked questions

How much does a hotel room cost in Winchester?
You can find top hotels in Winchester from CNY652 with options to suit your budget and needs. If you're looking for an affordable hotel in Winchester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.
How can I find deals and earn rewards at Winchester hotels?
Discover great deals on Winchester hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Winchester hotels.
Can I book Winchester hotels with free cancellation?
To book a refundable Winchester hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
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.