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Check prices for these dates

Tonight
Apr 13 - Apr 14
Tomorrow
Apr 14 - Apr 15
This weekend
Apr 17 - Apr 19
Next weekend
Apr 24 - Apr 26

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Our top choices for Winchester hotels

Basic Room, 1 Queen Bed, Valley View

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
10.0 out of 10, Exceptional, (2 reviews)
"Staff was friendly and accommodating "
Canada
James
The price is CA $109
CA $124 total
includes taxes & fees
Apr 14 - Apr 15
Windmill Motel Restaurant
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (162 reviews)
"We had a wonderful stay at The Burrell House. The room was large, beautifully renovated with a well thought out design. It is a very short walk or drive to Main Street where there were a multitude of restaurants and shops. We truly enjoyed our stay and plan to book again soon. "
United States
Melissa
The price is CA $203
CA $227 total
includes taxes & fees
Apr 20 - Apr 21
The Burrell House
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (133 reviews)
"The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. "
United States
John
The price is CA $140
CA $224 total
includes taxes & fees
Apr 15 - Apr 16
Blooming Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is CA $179
CA $195 total
includes taxes & fees
Apr 15 - Apr 16
Four Columns Inn
Exterior

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"Great Stay!"
United States
Nicholas
The price is CA $106
CA $117 total
includes taxes & fees
Apr 20 - Apr 21
The Putney Inn
Exterior

The Inn At Quail Run

The Inn At Quail Run
2.5 star property
Wilmington
9.0 out of 10, Wonderful, (72 reviews)
"Property was just as described, it was great staying there, outdoors was beautiful."
United States
Tami
The price is CA $270
CA $297 total
includes taxes & fees
Apr 14 - Apr 15
The Inn At Quail Run
Breakfast area

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,001 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is CA $99
CA $109 total
includes taxes & fees
Apr 20 - Apr 21
The Covered Bridge Inn
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (957 reviews)
"I wish I could have stayed longer. Very nice hotel "
United States
Rosa
The price is CA $163
CA $179 total
includes taxes & fees
Apr 22 - Apr 23
Hampton Inn Brattleboro
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,009 reviews)
"Great staff, great food, clean, friendly"
United States
Thomas
The price is CA $183
CA $205 total
includes taxes & fees
May 4 - May 5
The Colonial Hotel
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, (1,004 reviews)
"Clean room, polite staff,kids enjoyed the indoor heated pool they also have a small gym and breakfast in the morning couldn't beat the price definitely a great place for the family dogs are also welcome!!"
United States
Sean
The price is CA $178
CA $193 total
includes taxes & fees
Apr 16 - Apr 17
Keene Elm City Hotel, an Ascend Collection Hotel
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (351 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is CA $218
CA $240 total
includes taxes & fees
Apr 26 - Apr 27
Colonel Williams Inn
Front of property

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (490 reviews)
"Pet friendly for $15 plus tax. The place noisy with heat turned on in the room "
United States
Angela
The price is CA $133
CA $146 total
includes taxes & fees
Apr 16 - Apr 17
Black Mountain Inn
Lobby sitting area

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (17 reviews)
"Warm hospitality, very nice breakfast"
United States
Christopher
The price is CA $203
CA $220 total
includes taxes & fees
Apr 14 - Apr 15
Inn at Valley Farms
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is CA $191
CA $207 total
includes taxes & fees
Apr 14 - Apr 15
The Carriage Barn Inn
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,004 reviews)
"Nice rooms"
United States
Kim
The price is CA $199
CA $216 total
includes taxes & fees
Apr 14 - Apr 15
Best Western Plus Keene Hotel
Front of property

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (181 reviews)
"Great place and very clean!!"
United States
Emil
The price is CA $281
CA $328 total
includes taxes & fees
Apr 16 - Apr 17
Vikings Villages Resort
BBQ/picnic area

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)
2.5 star property
Peterborough
9.2 out of 10, Wonderful, (457 reviews)
"Room was clean, spacious and staff was pleasant. "
United States
Susan
The price is CA $144
CA $171 total
includes taxes & fees
Apr 30 - May 1
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (863 reviews)
"Great location, great staff really cool old building with lots of character"
Canada
David
The price is CA $176
CA $194 total
includes taxes & fees
Apr 14 - Apr 15
Latchis Hotel
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is CA $325
CA $358 total
includes taxes & fees
Apr 21 - Apr 22
The One Cat B&B
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (357 reviews)
"Perfect place for what we needed!"
United States
Cathleen
The price is CA $255
CA $284 total
includes taxes & fees
Apr 20 - Apr 21
The Inn At Crumpin Fox
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

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

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
Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

Recent Reviews in Winchester

Colonial Motel And Spa

Colonial Motel And Spa

2/10 Terrible
"I booked and paid ahead of time. I drove down 2.5 hrs to find it was completely shut down and not a running hotel. Very irritated I booked here because I was down there for a bowling tournament and the bowling alley basically shares a driveway. I had to go acrossed the street to holiday inn and luckily they had a vacancy, I had to pay $180 more than what I was expecting to pay, I haven’t gotten a refund. Also not sure why they are taking reservations when they are not even open for business. "
Jeremy 2-night trip
Posted 6 hours ago
Colonial Motel And Spa

More cheap stays in Winchester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road Brattleboro VT
The price is CA $99 per night from Apr 20 to Apr 21
CA $99
CA $109 total
Apr 20 - Apr 21
includes taxes & fees
7.6/10 Good! (1,001 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 $109 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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