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Winchester Hotels from S$113

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Check prices for these dates

Tonight
11 Jan - 12 Jan
Tomorrow
12 Jan - 13 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

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Our top choices for Winchester hotels

Breakfast area
The Covered Bridge Inn

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,004 reviews)
"Easy check in and good parking"
United States
nicholas
The price is S$119
includes taxes & fees
12 Jan - 13 Jan
The Covered Bridge Inn
Lobby
Keene Elm City Hotel, an Ascend Collection Hotel

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, (976 reviews)
"Staff was very welcoming and the room was very clean. "
United States
Rebecca
The price is S$168
includes taxes & fees
12 Jan - 13 Jan
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior
The Inn At Crumpin Fox

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (350 reviews)
"Very nice comfortable room. "
United States
deborah
The price is S$182
includes taxes & fees
16 Jan - 17 Jan
The Inn At Crumpin Fox
Indoor pool
Hampton Inn Brattleboro

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (935 reviews)
"Good breakfast, great staff and very good location "
United States
Valdeci
The price is S$208
includes taxes & fees
22 Jan - 23 Jan
Hampton Inn Brattleboro
Restaurant
Best Western Plus Keene Hotel

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)
"Great stay pool was very nice"
United States
Patrick
The price is S$194
includes taxes & fees
12 Jan - 13 Jan
Best Western Plus Keene Hotel
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (756 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is S$195
includes taxes & fees
15 Jan - 16 Jan
Comfort Inn & Suites Brattleboro I-91
Free daily continental breakfast
The Carriage Barn Inn

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is S$176
includes taxes & fees
12 Jan - 13 Jan
The Carriage Barn Inn
Exterior
The Putney Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"The room was okay for a quick stop to rest. "
United States
Janice
The Putney Inn
Interior
The Colonial Hotel

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,000 reviews)
"Easy checkin, pleasant staff and clean room. "
United States
Susan
The Colonial Hotel
Land view from property
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (18 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Lobby
Holiday Inn Express Hotel & Suites Brattleboro by IHG

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, (1,007 reviews)
"The hotel was very clean. Staff was extremely friendly and helpful."
United States
Stephanie
The price is S$215
includes taxes & fees
29 Jan - 30 Jan
Holiday Inn Express Hotel & Suites Brattleboro by IHG
In-room safe, desk, blackout curtains, iron/ironing board
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,002 reviews)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is S$113
includes taxes & fees
13 Jan - 14 Jan
Days Inn by Wyndham Keene NH
Free daily buffet breakfast
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (363 reviews)
"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 S$238
includes taxes & fees
8 Feb - 9 Feb
Hampton Inn & Suites Keene
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (342 reviews)
"Absolutely stunning bed and breakfast! The room and facilities were clean and welcoming. We really enjoyed the decorations and details of the house. The breakfast was delicious! Will definitely be coming back next time we are in town for ski! Highly recommended staying at Colonel Williams! "
United States
Ekaterina
The price is S$214
includes taxes & fees
12 Jan - 13 Jan
Colonel Williams Inn
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

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, (759 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is S$244
includes taxes & fees
17 Jan - 18 Jan
Fairfield Inn & Suites by Marriott Keene Downtown
Front of property
Black Mountain Inn

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (477 reviews)
"Room looked good. Wish they have shampoo. Only one soap. Nice shower pressure. Would visit again "
United States
Miles
The price is S$156
includes taxes & fees
12 Jan - 13 Jan
Black Mountain Inn
Reception
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (886 reviews)
"Friendly staff, great breakfast, comfy beds"
United States
Lori
The price is S$270
includes taxes & fees
18 Jan - 19 Jan
Hampton Inn & Suites Greenfield
Front of property
Blooming Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (128 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is S$203
includes taxes & fees
12 Jan - 13 Jan
Blooming Inn
BBQ/picnic Area
Riverhouse by Weekender (Formerly Jack Daniels Inn)

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, (443 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior
The Burrell House

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (156 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
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

Bennett Gorge

You can take time to visit Bennett Gorge during your travels to Richmond.
See properties

Cass Pond

Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.
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 city centre 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

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

10/10 Excellent
"Beds were sooo comfortable "
Catherine 1-night trip
Posted 6 days ago
Riverhouse by Weekender (Formerly Jack Daniels 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 S$113 per night from 13 Jan to 14 Jan
S$113
13 Jan - 14 Jan
includes taxes & fees
7/10 Good! (1,000 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 traveller data. Two other choices for your trip to the area are The Covered Bridge Inn and Comfort Inn & Suites Brattleboro I-91. 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: Features a sauna, an indoor pool and free self parking. Comfort Inn & Suites Brattleboro I-91 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 Cass Pond, Barden State Wildlife Management Area and Ashuelot River. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Bennett Gorge. 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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