Winchester Hotels from S$111

  • 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
26 Feb - 27 Feb
Tomorrow
27 Feb - 28 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Fitness facility

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.4 out of 10, Very good, (986 reviews)
"Staff were great place was clean and nice. "
United States
Alex
The price is S$149
includes taxes & fees
1 Mar - 2 Mar
Keene Elm City Hotel, an Ascend Collection Hotel
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)
"Great stay pool was very nice"
United States
Patrick
The price is S$163
includes taxes & fees
28 Feb - 1 Mar
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, (170 reviews)
"Great place and very clean!!"
United States
Emil
The price is S$283
includes taxes & fees
29 Mar - 30 Mar
Vikings Villages Resort
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (769 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is S$161
includes taxes & fees
28 Mar - 29 Mar
Comfort Inn & Suites Brattleboro I-91
Exterior

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (353 reviews)
"Staff very accomodating when we needed to check in very early"
United States
Bill
The price is S$179
includes taxes & fees
27 Feb - 28 Feb
The Inn At Crumpin Fox
In-room safe, desk, blackout curtains, 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, (1,000 reviews)
"Checkin was quick. I like the pre-check in process."
United States
Anthony
The price is S$111
includes taxes & fees
28 Feb - 1 Mar
Days Inn by Wyndham Keene NH
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (948 reviews)
"Good breakfast, great staff and very good location "
United States
Valdeci
The price is S$158
includes taxes & fees
4 Mar - 5 Mar
Hampton Inn Brattleboro
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$273
includes taxes & fees
28 Feb - 1 Mar
The One Cat B&B
Front of property

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (484 reviews)
"Instant check-in and check-out Very responsive and friendly staff. Clean and well maintained. Everything you need is provided. The room is spacious, and the beds are comfortable."
United States
Olga
The price is S$138
includes taxes & fees
2 Mar - 3 Mar
Black Mountain Inn
Breakfast area

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,001 reviews)
"Easy check in and good parking"
United States
nicholas
The price is S$113
includes taxes & fees
27 Feb - 28 Feb
The Covered Bridge Inn
Hypo-allergenic bedding, free WiFi, bed sheets

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is S$202
includes taxes & fees
8 Mar - 9 Mar
Colonel Williams Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (21 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Front of property

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (131 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is S$194
includes taxes & fees
2 Mar - 3 Mar
Blooming Inn
Desk, iron/ironing board, rollaway beds, free WiFi

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
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$313
includes taxes & fees
4 Mar - 5 Mar
The Inn At Quail Run
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,000 reviews)
"Well-kept hotel with a great restaurant."
United States
Adam
The Colonial Hotel
Lobby sitting area

Inn at Valley Farms

Inn at Valley Farms
2.0 star property
Walpole
10.0 out of 10, Exceptional, (15 reviews)
"Picturesque, family run bed and breakfast."
United States
Jay
The price is S$208
includes taxes & fees
1 Mar - 2 Mar
Inn at Valley Farms
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (158 reviews)
"The building and room were very nice. The location is great, very walkable to the center of town. "
United States
Rochelle
The Burrell House
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (169 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is S$209
includes taxes & fees
1 Mar - 2 Mar
The Carriage Barn Inn
Reception

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (889 reviews)
"Very clean, including a nice clean bathroom. Friendly staff."
United States
Jennifer
The price is S$219
includes taxes & fees
8 Mar - 9 Mar
Hampton Inn & Suites Greenfield
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

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
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

Barden State Wildlife Management Area

This serene wildlife reserve in New Hampshire offers undisturbed natural landscapes for wildlife observation. Bring binoculars for spotting native species while exploring the peaceful trails during spring through fall.
See properties

New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskies while learning about the distillation process in a warm space adorned with reclaimed wood.
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

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent
"Hotel was very clean, breakfast was great and staff were very helpful and courteous."
Michael 2-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is S$111 per night from 28 Feb to 1 Mar
S$111
28 Feb - 1 Mar
includes taxes & fees

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 Comfort Inn & Suites Brattleboro I-91 and Vikings Villages Resort. 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: Offers a sauna, an indoor pool and free self parking. Comfort Inn & Suites Brattleboro I-91 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 8 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 Barden State Wildlife Management Area, Cass Pond and Royalston State Forest. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Richmond Town Hall. 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