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

Find hotels in Winchester, NH from CA $106

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

Lobby
Standard Room, 1 King Bed, Non Smoking
Free buffet breakfast
Fitness facility

1. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
James
CA $185
CA $201 total
includes taxes & fees
Aug 30 - Aug 31
Keene Elm City Hotel, an Ascend Collection Hotel
Lobby
Lobby
Suite, 1 King Bed with Sofa bed, Non Smoking
Indoor pool, sun loungers

2. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Diane
CA $164
CA $180 total
includes taxes & fees
Sep 6 - Sep 7
Comfort Inn & Suites Brattleboro I-91
Indoor pool
Free breakfast
Lobby
Restaurant

3. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Timothy
CA $158
CA $174 total
includes taxes & fees
Sep 8 - Sep 9
Hampton Inn Brattleboro
Front of property
Interior
Children's activities
Exterior

4. Centennial House

Centennial House
Northfield
United States
Amy
CA $229
CA $242 total
includes taxes & fees
Sep 13 - Sep 14
Centennial House
Restaurant
Lobby
Premium bedding, desk, laptop workspace, blackout drapes
Property amenity

5. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Julia
CA $187
CA $203 total
includes taxes & fees
Sep 24 - Sep 25
Best Western Plus Keene Hotel
Deluxe Room, 1 Queen Bed, Valley View
Deluxe Room, 1 Queen Bed, Valley View | In-room dining
Front of property
Deluxe Room, 1 Queen Bed, Valley View | Television

6. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Dan
CA $168
CA $188 total
includes taxes & fees
Aug 31 - Sep 1
Windmill Motel Restaurant
Free daily continental breakfast
Concierge desk
Front of property - evening/night
Exterior detail

7. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
VINCENT JOEL
CA $96
CA $106 total
includes taxes & fees
Sep 7 - Sep 8
The Covered Bridge Inn
In-room safe, desk, blackout drapes, iron/ironing board
Fitness facility
Exterior
Lobby

8. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
Alex
CA $134
CA $146 total
includes taxes & fees
Sep 9 - Sep 10
Days Inn by Wyndham Keene NH
Free daily buffet breakfast
Reception
Exterior
Snack bar

9. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Christopher
CA $214
CA $232 total
includes taxes & fees
Sep 8 - Sep 9
Hampton Inn & Suites Keene
Exterior
Theatre show
Theatre show
Hiking

10. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Stark
CA $180
CA $198 total
includes taxes & fees
Aug 30 - Aug 31
Latchis Hotel
Lobby
Exterior
In-room safe, desk, blackout drapes, iron/ironing board
Exterior

11. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Marnie
CA $234
CA $257 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Lobby
Deluxe Single Room, 1 King Bed
Interior
Suite, 1 King Bed with Sofa bed

12. Colonial Motel

Colonial Motel
Brattleboro
United States
James
CA $114
CA $125 total
includes taxes & fees
Sep 1 - Sep 2
Colonial Motel
Exterior
Exterior
Courtyard view
Exterior

13. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Christopher
CA $225
CA $251 total
includes taxes & fees
Aug 31 - Sep 1
The Inn At Crumpin Fox
Front of property
Reception
Seasonal outdoor pool
Property entrance

14. Black Mountain Inn

Black Mountain Inn
Brattleboro
United States
Robert
CA $165
CA $181 total
includes taxes & fees
Sep 6 - Sep 7
Black Mountain Inn
Sundeck
Select Comfort beds, in-room safe, desk, blackout drapes
Select Comfort beds, in-room safe, desk, blackout drapes
Exterior

15. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Jason
CA $223
CA $241 total
includes taxes & fees
Sep 27 - Sep 28
Riverside Hotel, an Ascend Collection Hotel
Exterior
Deluxe Double Room | Private kitchenette
Staircase
Exterior

16. The Burrell House

The Burrell House
Keene
United States
Justin
CA $174
CA $194 total
includes taxes & fees
Sep 7 - Sep 8
The Burrell House
Free daily continental breakfast
Lounge
Restaurant
Exterior

17. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
CA $202
CA $220 total
includes taxes & fees
Aug 30 - Aug 31
The Carriage Barn Inn
Exterior
Property grounds
Standard Room, 2 Queen Beds, Refrigerator & Microwave
Exterior

18. The Putney Inn

The Putney Inn
Putney
United States
JANE
CA $136
CA $149 total
includes taxes & fees
Sep 24 - Sep 25
The Putney Inn
Front of property
Deluxe Chalet
32-inch Smart TV with cable channels, TV, fireplace
Exterior

19. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Melissa
CA $201
CA $234 total
includes taxes & fees
Sep 24 - Sep 25
Vikings Villages Resort
Exterior
Lobby
Loft, 1 King Bed with Sofa bed
Lobby

20. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
James
CA $240
CA $261 total
includes taxes & fees
Sep 6 - Sep 7
Fairfield Inn & Suites by Marriott Keene Downtown
View all properties
Save an average of 15% on thousands of hotels when you're signed in

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.
See properties

Cass Pond

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

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.
See properties

Barden State Wildlife Management Area

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

Richmond Wildlife Manangement Area

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

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.
See properties

Bennett Gorge

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

Conant Public Library

After visiting Conant Public Library, make a plan to see the other sights and activities in Winchester. While you're in the area, stroll along the lakeside.
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
A snow-covered town with a river running through it, surrounded by mountains and trees.

Top Winchester Hotel Reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"The staff was helpful. Parking was easy. It was an ok stay. I would stay there again for the price."
Deborah 1-night trip
Posted 12 hours ago
Days Inn by Wyndham Keene NH
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Has everything necessary for a two night stay."
Giovanna 2-night trip
Posted 12 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Latchis Hotel

Latchis Hotel

10/10 Excellent
"Great stay! Very clean."
Edward 1-night trip
Posted 12 hours ago
Latchis Hotel
Windmill Motel Restaurant

Windmill Motel Restaurant

10/10 Excellent
"Staff that I meet were friendly and helpful. The room was clean and what I had expected for what I paid and needed. If you need a place to crash and dont need frills this is perfectly acceptable. I would stay here again."
William 1-night trip
Posted 18 hours ago
Windmill Motel Restaurant
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"The property was excellent. Loved the pool and hot tub."
zavean 4-night trip
Posted 2 days ago
The Colonial Hotel
Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"my fav. vacation place!!!"
Melissa 1-night trip
Posted 2 days ago
Vikings Villages Resort
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"it was great, breakfast was great, staff was great. We did not get to use the pool and/or the workout room due to length of our stay. We did ask for a later check out and were granted that so that was helpful"
Sue 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG
The Putney Inn

The Putney Inn

8/10 Good
"Outward appearance was deceiving. The room was very nice and appeared to be newly remodeled."
Nancy 1-night trip
Posted 2 days ago
The Putney Inn
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"Spacious rooms, big balconies overlooking the river, and the whole hotel was VERY clean."
Jason 1-night trip
Posted 2 days ago
Riverside Hotel, an Ascend Collection Hotel

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
CA $134
CA $146 total
Sep 9 - Sep 10
includes taxes & fees
7/10 Good! (1,002 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
CA $137
CA $153 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (56 reviews)
Gardner Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
CA $158
CA $174 total
Sep 8 - Sep 9
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
CA $164
CA $180 total
Sep 6 - Sep 7
includes taxes & fees
8.6/10 Excellent! (849 reviews)
Comfort Inn & Suites Brattleboro I-91
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
CA $180
CA $198 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (969 reviews)
Latchis Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
CA $185
CA $201 total
Aug 30 - Aug 31
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Keene Elm City Hotel, an Ascend Collection 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 $106 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.

Explore a world of travel with Expedia