Winchester hotels from RM401

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Our top choices for Winchester hotels

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, (446 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,000 reviews)
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel

Gardner Inn

Gardner Inn
2.0 star property
Gardner
5.0 out of 10, (20 reviews)
"Clean room, comfy bed, quiet guests around my room. Staff was cordial when I checked in. "
United States
Kathy
The price is RM428
RM478 total
includes taxes & fees
1 Mar - 2 Mar
Gardner Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (131 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is RM364
RM597 total
includes taxes & fees
2 Mar - 3 Mar
Blooming Inn

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is RM1,069
RM1,069 total
includes taxes & fees
4 Mar - 5 Mar
The Maguire House Bed & Breakfast

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, (987 reviews)
"Staff were great place was clean and nice. "
United States
Alex
The price is RM424
RM460 total
includes taxes & fees
1 Mar - 2 Mar
Keene Elm City Hotel, an Ascend Collection Hotel

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,001 reviews)
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is RM700
RM759 total
includes taxes & fees
12 Mar - 13 Mar
Courtyard by Marriott Keene Downtown

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, (766 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is RM696
RM755 total
includes taxes & fees
7 Mar - 8 Mar
Fairfield Inn & Suites by Marriott Keene Downtown

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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,001 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is RM463
RM503 total
includes taxes & fees
28 Feb - 1 Mar
Best Western Plus Keene Hotel

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)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is RM369
RM401 total
includes taxes & fees
28 Feb - 1 Mar
Days Inn by Wyndham Keene NH

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (353 reviews)
"Staff very accomodating when we needed to check in very early"
United States
Bill
The price is RM493
RM551 total
includes taxes & fees
28 Feb - 1 Mar
The Inn At Crumpin Fox

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (15 reviews)
"Picturesque, family run bed and breakfast."
United States
Jay
The price is RM589
RM639 total
includes taxes & fees
1 Mar - 2 Mar
Inn at Valley Farms

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (890 reviews)
"Very clean, including a nice clean bathroom. Friendly staff."
United States
Jennifer
The price is RM602
RM673 total
includes taxes & fees
8 Mar - 9 Mar
Hampton Inn & Suites Greenfield

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (158 reviews)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (367 reviews)
"Clean, comfortable. "
United States
Jacklyn
The price is RM647
RM702 total
includes taxes & fees
29 Mar - 30 Mar
Hampton Inn & Suites Keene

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (169 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is RM589
RM639 total
includes taxes & fees
30 Mar - 31 Mar
The Carriage Barn Inn

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (170 reviews)
"Great place and very clean!!"
United States
Emil
The price is RM743
RM867 total
includes taxes & fees
29 Mar - 30 Mar
Vikings Villages Resort

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)
"Very clean room and super friendly staff!"
United States
Joanne
The price is RM557
RM613 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is RM912
RM1,003 total
includes taxes & fees
4 Mar - 5 Mar
Inn on Putney Road
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Stay near popular Winchester attractions

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 city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

More cheap stays in Winchester

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 traveller data. Two other choices for your trip to the area are Colonial Motel And Spa and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
What are some hotels with pools in Winchester?
The Colonial Hotel: Offers a sauna, an indoor pool and free self parking. Colonial Motel And Spa and Hampton Inn Brattleboro are a couple of other choices that offer an on-site pool. View all hotels with pools in Winchester.
What is staying in Winchester like?
Visitors to Winchester will definitely enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 8 hotels and other accommodation options to choose from. Find out more about Winchester.
What are the top places to visit in 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 itinerary are New England Sweetwater Farm & Distillery and Winchester Speedpark. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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