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

Winchester Hotels from S$130

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Check prices for these dates

Next weekend
17 Jul - 19 Jul
In two weeks
24 Jul - 26 Jul

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Our top choices for Winchester hotels

Iron/ironing board, travel cot, free WiFi, bed sheets

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 S$405
includes taxes & fees
19 Jul - 20 Jul
Deerfield Inn
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, (1,013 reviews)
"Staff was very professional and friendly"
United States
Ramica
The price is S$167
includes taxes & fees
13 Jul - 14 Jul
Keene Elm City Hotel, an Ascend Collection Hotel
Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.0 out of 10, Wonderful, (25 reviews)
"Clean room, good prices, friendly staff"
United States
Amy
The price is S$175
includes taxes & fees
14 Jul - 15 Jul
Windmill Motel Restaurant
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,015 reviews)
"Great staff. Clean and comfortable. Fantastic breakfast. Loved the Andes mints."
United States
Gordon
The price is S$167
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Keene Hotel
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (1,007 reviews)
"A little overpriced but a good stay"
United States
David
The price is S$174
includes taxes & fees
11 Aug - 12 Aug
Hampton Inn Brattleboro
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (356 reviews)
"Great breakfast!"
United States
Billie
The price is S$224
includes taxes & fees
15 Jul - 16 Jul
Colonel Williams 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 S$243
includes taxes & fees
14 Jul - 15 Jul
The Carriage Barn Inn
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (926 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 S$183
includes taxes & fees
14 Jul - 15 Jul
Latchis Hotel
Exterior

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (173 reviews)
"Self check-in and checkout. Room was very clean but a bit too much potpourri for my allergies. Will stay here again when in Keene. "
United States
Charles
The price is S$195
includes taxes & fees
20 Jul - 21 Jul
The Burrell House
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 S$189
includes taxes & fees
26 Jul - 27 Jul
Comfort Inn & Suites Brattleboro I-91
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, (1,002 reviews)
"The staff was able to recommend places to go and eat, which was really nice."
United States
Alyssa
The price is S$184
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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 S$234
includes taxes & fees
15 Jul - 16 Jul
The Inn At Crumpin Fox
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 S$260
includes taxes & fees
14 Jul - 15 Jul
Vikings Villages Resort
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, (1,009 reviews)
"Great breakfast, friendly staff and good place to stay."
United States
Michael
The price is S$130
includes taxes & fees
23 Jul - 24 Jul
Days Inn by Wyndham Keene NH
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 S$224
includes taxes & fees
26 Jul - 27 Jul
Hampton Inn & Suites Greenfield
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 S$219
includes taxes & fees
13 Jul - 14 Jul
Blooming Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (46 reviews)
"The hot tub was so amazing"
United States
Mark
The price is S$298
includes taxes & fees
13 Jul - 14 Jul
Four Columns Inn
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,011 reviews)
"Food at restaurant was phenomenal"
United States
Zachary
The price is S$221
includes taxes & fees
19 Jul - 20 Jul
The Colonial Hotel
Front of property

Gardner Inn

Gardner Inn
2.0 star property
Gardner
7.6 out of 10, Good, (34 reviews)
"Great for a quick stay while passing through!"
United States
Cristen
The price is S$143
includes taxes & fees
19 Jul - 20 Jul
Gardner Inn
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is S$345
includes taxes & fees
16 Jul - 17 Jul
The One Cat B&B
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

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

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

Top Winchester Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Front desk staff extremely helpful. The property interior and exterior was very well maintained. One of the best Best Western hotels Iā€™ve stayed at."
Ruben 1-night trip
Posted 9 hours ago
Best Western Plus Keene Hotel

More cheap stays in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
The price is S$162 per night from 22 Jul to 23 Jul
S$162
22 Jul - 23 Jul
includes taxes & fees
8.4/10 Very good! (1,003 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
The Colonial Hotel, located 2.1 mi (3.5 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 Keene Elm City Hotel, an Ascend Collection Hotel and Best Western Plus Keene Hotel. 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. Keene Elm City Hotel, an Ascend Collection Hotel and Best Western Plus Keene Hotel 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, Royalston State Forest and Rhododendron State Park. A couple of additional sights to add to your itinerary are Winchester Speedpark and New England Sweetwater Farm & Distillery. 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 19Ā°C, while the coldest months are January and February, with an average of -2Ā°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

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