Winchester Hotels from S$99

  • 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
12 Apr - 13 Apr
Tomorrow
13 Apr - 14 Apr
Next weekend
17 Apr - 19 Apr
In two weeks
24 Apr - 26 Apr

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
10.0 out of 10, Exceptional, (1 review)
"Staff was friendly and accommodating "
Canada
James
The price is S$114
includes taxes & fees
13 Apr - 14 Apr
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 S$156
includes taxes & fees
13 Apr - 14 Apr
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 S$206
includes taxes & fees
13 Apr - 14 Apr
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 S$178
includes taxes & fees
13 Apr - 14 Apr
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 S$103
includes taxes & fees
27 Apr - 28 Apr
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 S$273
includes taxes & fees
13 Apr - 14 Apr
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 S$99
includes taxes & fees
14 Apr - 15 Apr
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 S$165
includes taxes & fees
22 Apr - 23 Apr
Hampton Inn Brattleboro
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,007 reviews)
"Great staff, great food, clean, friendly"
United States
Thomas
The price is S$205
includes taxes & fees
14 Apr - 15 Apr
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, (1,003 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 S$177
includes taxes & fees
15 Apr - 16 Apr
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, (350 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is S$205
includes taxes & fees
26 Apr - 27 Apr
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 S$135
includes taxes & fees
13 Apr - 14 Apr
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 S$195
includes taxes & fees
13 Apr - 14 Apr
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 S$182
includes taxes & fees
13 Apr - 14 Apr
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, (1,001 reviews)
"Nice rooms"
United States
Kim
The price is S$199
includes taxes & fees
13 Apr - 14 Apr
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 S$302
includes taxes & fees
13 Apr - 14 Apr
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 S$187
includes taxes & fees
19 Apr - 20 Apr
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 S$168
includes taxes & fees
15 Apr - 16 Apr
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 S$333
includes taxes & fees
18 Apr - 19 Apr
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 S$262
includes taxes & fees
13 Apr - 14 Apr
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.
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

Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.
See properties

Cass Pond

This serene 54-acre pond in Richmond offers peaceful fishing for bass, pickerel, and perch. Bring your own gear and a valid New Hampshire fishing licence to fully enjoy this tranquil natural retreat.
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 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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"The breakfast was not very good. "
Becky 1-night trip
Posted 1 hour ago
Hampton Inn Brattleboro

More cheap stays in Winchester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road Brattleboro VT
The price is S$99 per night from 14 Apr to 15 Apr
S$99
14 Apr - 15 Apr
includes taxes & fees
7.6/10 Good! (1,001 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 Colonial Motel And Spa and Hampton Inn Brattleboro. 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. Colonial Motel And Spa and Hampton Inn Brattleboro 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 7 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 Cass Pond, Rhododendron State Park and Royalston State Forest. 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.

Explore a world of travel with Expedia