Winchester Hotels from S$96

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27 Nov - 28 Nov
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Top 10 trending Winchester hotels

Interior
The Colonial Hotel

The Colonial Hotel

3.0 star property
Gardner
8.8 out of 10, Excellent, (1010)
"Great hotel, fantastic restaurant, wonderful place!"
United States
Kate
The Colonial Hotel
Front of property
The Inn At Crumpin Fox

The Inn At Crumpin Fox

2.5 star property
Bernardston
9.2 out of 10, Wonderful, (342)
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
United States
Christine
The price is S$189
includes taxes & fees
1 Dec - 2 Dec
The Inn At Crumpin Fox
Exterior detail
The Covered Bridge Inn

The Covered Bridge Inn

2.5 star property
Brattleboro
7.6 out of 10, Good, (1006)
"Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests."
United States
Zachery
The price is S$108
includes taxes & fees
30 Nov - 1 Dec
The Covered Bridge Inn
Free daily on-the-go breakfast
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, (1002)
"Friendly, efficient staff and a very clean and nice room"
United States
Margaret
The price is S$182
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free WiFi
Gardner Inn

Gardner Inn

2.0 star property
Gardner
5.6 out of 10, (15)
"The property needs work but hte staff was pleasant and the facility was quiet. "
United States
Lou
The price is S$143
includes taxes & fees
30 Nov - 1 Dec
Gardner Inn
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very good, (1006)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is S$196
includes taxes & fees
2 Dec - 3 Dec
Best Western Plus Keene Hotel
Breakfast 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, (433)
"Super cute place! Would stay here again"
United States
Danielle
The price is S$190
includes taxes & fees
30 Nov - 1 Dec
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Front of property
Black Mountain Inn

Black Mountain Inn

2.0 star property
Brattleboro
7.4 out of 10, Good, (474)
"Clean, very friendly staff. Will stay again."
United States
Scot
The price is S$157
includes taxes & fees
8 Dec - 9 Dec
Black Mountain Inn
Sun deck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (626)
"Clean room, beautiful location"
United States
Marcie
The price is S$215
includes taxes & fees
28 Dec - 29 Dec
Riverside Hotel, an Ascend Collection Hotel
Reception
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 star property
Brattleboro
6.0 out of 10, (735)
"Reasonable rate for the the accomadations."
United States
David
The price is S$96
includes taxes & fees
30 Nov - 1 Dec
Travelodge by Wyndham Brattleboro VT
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (732)
"Absolutely perfect stay for a business trip"
United States
Lyndsey
The price is S$172
includes taxes & fees
14 Dec - 15 Dec
Comfort Inn & Suites Brattleboro I-91
Hiking
Latchis Hotel

Latchis Hotel

2.5 star property
Brattleboro
8.4 out of 10, Very good, (832)
"Great stay"
United States
Jason
The price is S$177
includes taxes & fees
30 Nov - 1 Dec
Latchis Hotel
Free breakfast
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 star property
Brattleboro
8.2 out of 10, Very good, (923)
"The room was very clean, and both staff and service were outstanding."
United States
Wonji
The price is S$204
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn Brattleboro
In-room safe, desk, blackout curtains, 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, (1003)
"Very professional people good service good staff "
United States
George
The price is S$129
includes taxes & fees
14 Dec - 15 Dec
Days Inn by Wyndham Keene NH
Down duvets, desk, blackout curtains, soundproofing
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 star property
Greenfield
8.6 out of 10, Excellent, (875)
"Friendly staff, great breakfast, comfy beds"
United States
Lori
The price is S$265
includes taxes & fees
3 Dec - 4 Dec
Hampton Inn & Suites Greenfield
Exterior
Colonial Motel And Spa

Colonial Motel And Spa

3.0 star property
Brattleboro
6.8 out of 10, (1003)
"Nice place to stay for the night."
United States
Robin
The price is S$171
includes taxes & fees
2 Dec - 3 Dec
Colonial Motel And Spa
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, (753)
"Front desk pleasant and helpful Breakfast was good Room was spacious and clean Able to walk to shopping and dining. "
United States
Stephen
The price is S$232
includes taxes & fees
14 Dec - 15 Dec
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior
The Putney Inn

The Putney Inn

2.5 star property
Putney
8.4 out of 10, Very good, (1002)
"The Putney Inn is a great place to stay!! The people who work there are very nice and the location is great!"
United States
Kristen
The Putney Inn
Reception
Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

2.5 star property
Keene
8.8 out of 10, Excellent, (349)
"Nice place to stay, nice area, will stay again."
United States
Catherine
The price is S$207
includes taxes & fees
24 Dec - 25 Dec
Hampton Inn & Suites Keene
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (12)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns 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

You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.
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Winchester Speedpark

You can take time to visit Winchester Speedpark during your travels to Winchester. While you're in the area, stroll along the lakeside.
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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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Great place. Historic—not for people who want fancy but clean with comfortable beds, very walkable to everything. Loved it!"
Heather 1-night trip
Posted 20 hours ago
Latchis Hotel

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$129 per night from 14 Dec to 15 Dec
S$129
14 Dec - 15 Dec
includes taxes & fees
7/10 Good! (1,002 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 Hampton Inn Brattleboro and Hampton Inn & Suites Greenfield. 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. Hampton Inn Brattleboro and Comfort Inn & Suites Brattleboro I-91 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 6 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 Birch Point, 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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