A snow-covered town with a river running through it, surrounded by mountains and trees.

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Our top choices for Winchester hotels

A two-story house with a red door, green shutters, and a snow-covered front yard.
A dining area with round tables, chairs, and a kitchen counter with a refrigerator.
A golf course with a brick pathway, wooden boxes, and a tee box.
A group of women in formal attire standing in a garden with a house in the background.

1. Centennial House

Centennial House
Northfield
United Kingdom
Alan
CA $237
CA $251 total
includes taxes & fees
Nov 4 - Nov 5
Centennial House
A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.
A large, single-story building with a central entrance and a covered walkway.
A room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.
A flat-screen TV mounted on a wall displaying a streaming service interface.

2. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Donna
CA $160
CA $179 total
includes taxes & fees
Nov 4 - Nov 5
Windmill Motel Restaurant
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.

3. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Lisa
CA $178
CA $194 total
includes taxes & fees
Oct 26 - Oct 27
Keene Elm City Hotel, an Ascend Collection Hotel
A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.
A brick building with a red awning and a sign that reads "The Inn."
A conference table set for a meeting with chairs and folded red napkins.
A gazebo with a red roof and white walls, surrounded by trees and a brick building.

4. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Heather
CA $158
CA $177 total
includes taxes & fees
Nov 2 - Nov 3
The Inn At Crumpin Fox
A hotel room with two beds, a TV, a desk, and a window with curtains.
A Days Inn with a brick facade, a central entrance, and a parking lot.
A reception area with a black marble counter, wooden cabinets, and a 'Staff Only' door.
A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.

5. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
CA $130
CA $141 total
includes taxes & fees
Oct 26 - Oct 27
Days Inn by Wyndham Keene NH
The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.
A banquet hall with round tables, chairs, and a staircase.
A covered bridge with a stone foundation, surrounded by lush greenery and a well-maintained lawn.
A lobby with a central circular platform, a statue, and a fountain. There are paintings on the walls and a staircase to the left.

6. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Erik
CA $199
CA $219 total
includes taxes & fees
Nov 3 - Nov 4
Latchis Hotel
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.
A compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.
A spacious lobby with a stone wall, a reception desk, and a large window.

7. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Faith
CA $152
CA $167 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn Brattleboro
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.

8. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
CA $154
CA $170 total
includes taxes & fees
Nov 22 - Nov 23
Comfort Inn & Suites Brattleboro I-91
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.
A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

9. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Timothy
CA $190
CA $209 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Hotel & Suites Brattleboro by IHG
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A hotel room with two beds, a nightstand, a lamp, and a chair.
A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.

10. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
United States
Luis
CA $140
CA $154 total
includes taxes & fees
Nov 22 - Nov 23
Econo Lodge Brattleboro South
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.
A covered outdoor area with a wooden deck, white railings, and string lights.

11. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
CA $199
CA $216 total
includes taxes & fees
Nov 4 - Nov 5
Best Western Plus Keene Hotel
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.
A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

12. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Neil
CA $228
CA $247 total
includes taxes & fees
Nov 19 - Nov 20
Hampton Inn & Suites Keene
A dock extending into a lake with a grassy area in the foreground and trees in the background.
A spacious living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.
A building with a large balcony overlooking a body of water, a bridge in the foreground, and trees with autumn foliage.
A spacious bedroom with a large bed, a desk, and a television.

13. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Steve
CA $214
CA $232 total
includes taxes & fees
Nov 21 - Nov 22
Riverside Hotel, an Ascend Collection Hotel
A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.
A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.
A wooden interior with a fireplace, a staircase, and a dining area.
A wooden log cabin with a snow-covered entrance and a wooden fence in a snowy forest.

14. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Cecil
CA $263
CA $307 total
includes taxes & fees
Nov 16 - Nov 17
Vikings Villages Resort
A hotel with a clock tower, a parking lot, and a well-maintained garden.
A hotel room with a bed, two bedside lamps, a nightstand, a chair, and a small table.
A building entrance with a white door, number 959, and a small porch area decorated with pumpkins, flowers, and scarecrows.
A swimming pool with lounge chairs and a covered umbrella.

15. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Ron
CA $177
CA $194 total
includes taxes & fees
Nov 22 - Nov 23
Black Mountain Inn
A dining area with a table and four chairs, a painting of a covered bridge, and a painting of a red building.
A multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.
A reception area with a stone counter, wooden reception desk, and a red carpet.
A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.

16. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
Rick
CA $148
CA $162 total
includes taxes & fees
Oct 26 - Oct 27
The Covered Bridge Inn
A wooden table set with plates, cutlery, and a folded napkin.
A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.
A two-story building with a porch, a sign indicating guest rooms, and an American flag.
A bench in front of an apple tree with ripe apples.

17. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Richard
CA $197
CA $214 total
includes taxes & fees
Oct 28 - Oct 29
The Carriage Barn Inn
A reception area with a counter, a computer, and various informational posters on the wall.
A reception desk with a computer, a clock, and a refrigerator.
A hotel room with a bed, bedside table, lamp, and a mirror.
A motel with a central staircase, multiple rooms, and a parking lot.

18. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
Brattleboro
United States
Nicolas
CA $129
CA $142 total
includes taxes & fees
Nov 5 - Nov 6
Travelodge by Wyndham Brattleboro VT
A cozy living room with a fireplace, a coffee station, and a view of the outside.
A dining table with a vase of flowers, a chair, and a window with a view.
A motel with multiple floors, each with balconies and windows.
A hotel room with a sofa, a coffee table, a desk with a telephone, a mirror, and a television.

19. Colonial Motel

Colonial Motel
Brattleboro
United States
Swaraj
CA $125
CA $138 total
includes taxes & fees
Nov 2 - Nov 3
Colonial Motel
A historic brick building with a porch and a sign reading "Burrell House."
A bedroom with a large bed, a wooden desk, and three chairs. There are three windows with shutters.
A covered outdoor seating area with tables and chairs, overlooking a residential street with houses and a road.
A kitchen with a microwave, coffee maker, and a KUPPST refrigerator. There are two stools and a small shelf with a vase.

20. The Burrell House

The Burrell House
Keene
United States
Carol
CA $190
CA $212 total
includes taxes & fees
Nov 2 - Nov 3
The Burrell House
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Stay near popular Winchester attractions

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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Richmond Wildlife Manangement Area

Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.
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Cass Pond

Commune with nature and explore the great outdoors at Cass Pond during your travels in Richmond.
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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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Barden State Wildlife Management Area

Explore the great outdoors at Barden State Wildlife Management Area, a lovely green space in Richmond.
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Attleboro Mountain

Commune with nature and explore the great outdoors at Attleboro Mountain during your travels in Richmond.
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Loring Field

Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.
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Bennett Gorge

You can take time to visit Bennett Gorge during your travels to Richmond.
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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 downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

Top Winchester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Good location. Well appointed room. Clean, updated. Comp breakfast was okay. TV was outdated but WiFi was strong."
John 1-night trip
Posted 1 hour ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Would absolutely stay again. Safe, clean, friendly, and adorable."
Jessica 1-night trip
Posted 3 hours ago
The Colonial Hotel
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

10/10 Excellent
"Clean room, but very old and needs updating. TV had Netflix and Prime."
Nazia 2-night trip
Posted 4 hours ago
Travelodge by Wyndham Brattleboro VT
Latchis Hotel

Latchis Hotel

8/10 Good
"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."
Matthew 1-night trip
Posted 8 hours ago
Latchis Hotel
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"Loved view of the river"
Steve 1-night trip
Posted 8 hours ago
Riverside Hotel, an Ascend Collection Hotel
Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Could not have been happier with the experience and the stay. This may look like a rustic cabin stay, but the cabins are not rustic and are very thoughtfully decorated with the Viking theme. Relax in these luxury cabins and take part in some onsite games to learn about the history of vikings. No costumes needed."
Cheri 4-night trip
Posted 14 hours ago
Vikings Villages Resort
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"Clean comfortable room with a comfortable bed. I didn’t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all it’s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."
Judith 1-night trip
Posted 1 day ago
Days Inn by Wyndham Keene NH
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The hotel was fairly new. Coffee was the only thing I felt needed changed."
Debbie 1-night trip
Posted 1 day ago
Hampton Inn Brattleboro
Colonial Motel

Colonial Motel

8/10 Good
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Andrea 3-night trip
Posted 2 days ago
Colonial Motel

More cheap stays in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
CA $108
CA $118 total
Nov 22 - Nov 23
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
The Putney Inn
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
CA $130
CA $141 total
Oct 26 - Oct 27
includes taxes & fees
7/10 Good! (1,003 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
CA $149
CA $167 total
Nov 1 - Nov 2
includes taxes & fees
Gardner Inn
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
CA $154
CA $170 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (889 reviews)
Comfort Inn & Suites Brattleboro I-91
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
CA $178
CA $194 total
Oct 26 - Oct 27
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
CA $199
CA $219 total
Nov 3 - Nov 4
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Latchis Hotel

Hotels in Winchester with star rating

Frequently asked questions

When is the best time to go to Winchester?
The best time to visit Winchester, New Hampshire, is during the autumn months, particularly from late September to late October, for the spectacular fall foliage.This period offers clear, crisp weather and the vibrant colours of the changing leaves, making it ideal for outdoor activities like hiking, scenic drives, and exploring the local countryside. The area surrounding Winchester is known for its natural beauty, with various trails and viewpoints to experience the seasonal display.Couples looking for a romantic getaway will find this time particularly appealing. The picturesque landscapes provide a beautiful backdrop for leisurely drives through the New Hampshire countryside or cosy evenings by a fireplace. Many local inns and B&Bs offer special packages during the fall.Families will also enjoy visiting in autumn. The cooler temperatures are superb for outdoor adventures without the summer heat, and there are often local harvest festivals or apple-picking opportunities in the wider region.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from CA $118 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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