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

Find hotels in Winchester, NH from CA $142

  • 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

This weekend
Jul 17 - Jul 19
Next weekend
Jul 24 - Jul 26

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Winchester hotels

Hotel
Exterior

Shelburne Springs

Shelburne Springs
2.0 star property
Shelburne
The price is CA $572
CA $639 total
includes taxes & fees
Jul 15 - Jul 16
Shelburne Springs
Lobby

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,015 reviews)
"Staff was very professional and friendly"
United States
Ramica
The price is CA $168
CA $183 total
includes taxes & fees
Jul 22 - Jul 23
Keene Elm City Hotel, an Ascend Collection Hotel
Deluxe Room, 1 Queen Bed, Valley View

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.0 out of 10, Wonderful, (28 reviews)
"Clean room, good prices, friendly staff"
United States
Amy
The price is CA $172
CA $192 total
includes taxes & fees
Jul 16 - Jul 17
Windmill Motel Restaurant
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,000 reviews)
"A little overpriced but a good stay"
United States
David
The price is CA $179
CA $197 total
includes taxes & fees
Jul 28 - Jul 29
Hampton Inn Brattleboro
Superior Single Room, 1 Queen Bed

Deerfield Inn

Deerfield Inn
3.0 star property
Deerfield
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed all aspects of our stay. The Inn was incredibly charming and comfortable. We will definitely be back."
United States
Dan
The price is CA $333
CA $433 total
includes taxes & fees
Jul 15 - Jul 16
Deerfield Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (357 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is CA $214
CA $235 total
includes taxes & fees
Jul 30 - Jul 31
Colonel Williams Inn
In-room safe, desk, blackout drapes, 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, (1,012 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is CA $131
CA $142 total
includes taxes & fees
Jul 28 - Jul 29
Days Inn by Wyndham Keene NH
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,018 reviews)
"Staff was very friendly, accommodating, and attentive to our needs. Room was clean and comfortable!"
United States
Helen
The price is CA $169
CA $183 total
includes taxes & fees
Aug 11 - Aug 12
Best Western Plus Keene Hotel
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (928 reviews)
"This hotel was the perfect landing place from a lot of traveling. It was clean, had unique historic ambience, and walkable to the whole town. Highly recommend!"
United States
Laurel
The price is CA $182
CA $200 total
includes taxes & fees
Jul 19 - Jul 20
Latchis Hotel
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (833 reviews)
"Staff wasfriendly and my room is very clean"
United States
Michael
The price is CA $192
CA $211 total
includes taxes & fees
Aug 11 - Aug 12
Comfort Inn & Suites Brattleboro I-91
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Wonderful stay"
United States
Justin
The price is CA $214
CA $238 total
includes taxes & fees
Jul 19 - Jul 20
The Burrell House
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (141 reviews)
"Appealing common spaces, lovely selections at the coffee/tea station, library and games. Everything for a cozy respite in a great location. Walk to the local village and attractions, central to exploring the Mohawk Trail."
United States
Annette
The price is CA $167
CA $256 total
includes taxes & fees
Jul 19 - Jul 20
Blooming Inn
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (376 reviews)
"Fantastic breakfast!"
United States
allisha
The price is CA $230
CA $257 total
includes taxes & fees
Jul 16 - Jul 17
The Inn At Crumpin Fox
Pool

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (926 reviews)
"Check in was very good. Customer service was exceptional. The room however smelled of cigarette smoke. Overall a good experience."
United States
Joseph
The price is CA $246
CA $275 total
includes taxes & fees
Jul 26 - Jul 27
Hampton Inn & Suites Greenfield
Lobby

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,003 reviews)
"The staff was able to recommend places to go and eat, which was really nice."
United States
Alyssa
The price is CA $190
CA $209 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Front of property

Gardner Inn

Gardner Inn
2.0 star property
Gardner
7.6 out of 10, Good, (35 reviews)
"Great for a quick stay while passing through!"
United States
Cristen
The price is CA $140
CA $157 total
includes taxes & fees
Jul 19 - Jul 20
Gardner Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (174 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is CA $218
CA $237 total
includes taxes & fees
Jul 19 - Jul 20
The Carriage Barn Inn
Front of property

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (497 reviews)
"Bed was comfy. Room was clean. "
United States
Katherine
The price is CA $205
CA $226 total
includes taxes & fees
Jul 21 - Jul 22
Black Mountain Inn
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,013 reviews)
"Food at restaurant was phenomenal"
United States
Zachary
The price is CA $216
CA $242 total
includes taxes & fees
Jul 19 - Jul 20
The Colonial Hotel
Front of property

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (207 reviews)
"It was very unique and great"
United States
Christopher
The price is CA $244
CA $285 total
includes taxes & fees
Jul 16 - Jul 17
Vikings Villages Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

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

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Did eat breakfast at the hotel. Room was clean"
Margaret 2-night trip
Posted 2 hours ago
The Colonial Hotel

More cheap stays in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
The price is CA $156 per night from Jul 27 to Jul 28
CA $156
CA $172 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very good! (1,006 reviews)

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 can I save on a Winchester hotel booking with Expedia?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 $142 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