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Jan 29 - Jan 30
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Jan 30 - Jan 31
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Jan 30 - Feb 1
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Feb 6 - Feb 8

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Our top choices for Winchester hotels

BBQ/picnic area

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.4 out of 10, Exceptional, (444 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Tranquil country hotel with refreshing indoor pool and spa services.
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel
Lobby

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.2 out of 10, (19 reviews)
  • cleanliness
    Stay at this scenic Gardner hotel with free parking and WiFi.
"Clean room, comfy bed, quiet guests around my room. Staff was cordial when I checked in. "
United States
Kathy
The price is ￥16,845
￥18,816 total
includes taxes & fees
Feb 1 - Feb 2
Gardner Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (130 reviews)
  • cleanliness
    Discover riverside charm in Shelburne Falls with free WiFi and winter activities.
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is ￥13,783
￥22,899 total
includes taxes & fees
Feb 1 - Feb 2
Blooming Inn
Free daily full breakfast

Centennial House

Centennial House
3.5 star property
Northfield
9.6 out of 10, Exceptional, (173 reviews)
  • cleanliness
    Stay by the golf course in this historic colonial B&B with daily breakfast.
"great proprietors beautiful vintage home excellent breakfast"
United States
JAMES
The price is ￥25,951
￥27,430 total
includes taxes & fees
Feb 14 - Feb 15
Centennial House
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)
  • cleanliness
    Cozy lakeside B&B in Ashburnham with full breakfast and outdoor activities.
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is ￥39,168
￥39,168 total
includes taxes & fees
Feb 12 - Feb 13
The Maguire House Bed & Breakfast
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (760 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is ￥26,034
￥28,247 total
includes taxes & fees
Feb 8 - Feb 9
Fairfield Inn & Suites by Marriott Keene Downtown
Lobby

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very Good, (979 reviews)
  • cleanliness
    Modern hotel with a convenient location in Keene near shopping and dining.
"Reasonably priced and clean."
United States
Justin
The price is ￥18,224
￥19,773 total
includes taxes & fees
Feb 1 - Feb 2
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,000 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn
Pub

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Experience downtown Keene's Art Deco charm with indoor pool and fitness center.
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is ￥27,565
￥29,908 total
includes taxes & fees
Feb 8 - Feb 9
Courtyard by Marriott Keene Downtown
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Peaceful stay in Keene with included breakfast and convenient river access.
"Great stay pool was very nice"
United States
Patrick
The price is ￥21,286
￥23,096 total
includes taxes & fees
Feb 1 - Feb 2
Best Western Plus Keene 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)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is ￥12,366
￥13,417 total
includes taxes & fees
Feb 1 - Feb 2
Days Inn by Wyndham Keene NH
Lobby sitting area

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (14 reviews)
  • cleanliness
    Charming Walpole inn with garden views near Hooper Golf Course and free perks.
"Picturesque, family run bed and breakfast."
United States
Jay
The price is ￥23,763
￥25,783 total
includes taxes & fees
Feb 1 - Feb 2
Inn at Valley Farms
Reception

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (887 reviews)
  • cleanliness
    Comfortable retreat near Old Greenfield Village with free daily buffet.
"Very clean, including a nice clean bathroom. Friendly staff."
United States
Jennifer
The price is ￥24,487
￥27,353 total
includes taxes & fees
Feb 4 - Feb 5
Hampton Inn & Suites Greenfield
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (352 reviews)
  • cleanliness
    Enjoy scenic Bernardston with convenient hiking and biking trail access.
"Staff very accomodating when we needed to check in very early"
United States
Bill
The price is ￥19,433
￥21,706 total
includes taxes & fees
Jan 31 - Feb 1
The Inn At Crumpin Fox
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156 reviews)
  • cleanliness
    Charming guesthouse in Keene with free WiFi and parking for a relaxed stay.
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House
Free daily buffet breakfast

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (364 reviews)
  • cleanliness
    Stay close to Ashuelot River in a comfortable hotel with an indoor pool.
"Room is very clean , breakfast is good and fresh .coffee serve well all time . Will back to stay again . "
United States
Raymond
The price is ￥25,924
￥28,127 total
includes taxes & fees
Feb 22 - Feb 23
Hampton Inn & Suites Keene
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
  • cleanliness
    Charming B&B retreat in Keene offers free breakfast and easy access to local art.
"Very helpful and welcoming host. "
United States
Bruce
The price is ￥20,635
￥22,389 total
includes taxes & fees
Feb 1 - Feb 2
The Carriage Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (19 reviews)
  • cleanliness
    Charming B&B in Newfane with garden-view tavern and complimentary perks.
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Exterior

Monadnock Inn

Monadnock Inn
2.5 star property
Jaffrey
7.6 out of 10, Good, (278 reviews)
  • cleanliness
    Historic inn overlooking the golf course offers charm and outdoor adventure.
"The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. "
United States
E S
Monadnock 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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Stay near popular Winchester attractions

New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskeys while learning about the distillation process in a warm space adorned with reclaimed wood.
See properties

Bennett Gorge

This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.
See properties

Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Staff and room were great, even let me check in at 1:30am after getting stuck in the recent storm. The room was spotless and comfortable. "
Martin 1-night trip
Posted 2 days ago
The Putney Inn

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is ￥12,366 per night from Feb 1 to Feb 2
￥12,366
￥13,417 total
Feb 1 - Feb 2
includes taxes & fees
7/10 Good! (999 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
The Colonial Hotel, located 26.3 mi (42.3 km) from the heart of Winchester, is a top choice for your stay based on our traveler data. Other good options for your stay in the area are Comfort Inn & Suites Brattleboro I-91 and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: You might want to consider this vacation home rental near Winchester, which is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.
What are some hotels with pools in Winchester?
The Colonial Hotel: Features a sauna, an indoor pool, and free self parking. Comfort Inn & Suites Brattleboro I-91 and Hampton Inn Brattleboro are two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is the best hotel near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
What is staying in Winchester like?
Visitors to Winchester are sure to enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 8 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Natural beauty is on display at Barden State Wildlife Management Area, Ashuelot River, and Cass Pond. A couple of additional sights to add to your agenda are New England Sweetwater Farm & Distillery and Bennett Gorge. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.

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