Winchester Hotels

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Our top choices for Winchester hotels

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.2 out of 10, Wonderful, (9 reviews)
"Clean room, good prices, friendly staff"
United States
Amy
The price is €128
includes taxes & fees
10 May - 11 May
Windmill Motel Restaurant

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (36 reviews)
"The hot tub was so amazing"
United States
Mark
The price is €121
includes taxes & fees
10 May - 11 May
Four Columns Inn

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 €182
includes taxes & fees
10 May - 11 May
The Inn At Quail Run

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (353 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is €147
includes taxes & fees
12 May - 13 May
Colonel Williams Inn

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (972 reviews)
"Clean room, great included breakfast, staff was nice and overall was just a good time"
United States
Savanna
The price is €118
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn Brattleboro

The Burrell House

The Burrell House
2.5 star property
Keene
9.6 out of 10, Exceptional, (163 reviews)
"It was a perfect location and the house is lovely. Will consider revisiting when the need arises. "
United States
Justin
The price is €132
includes taxes & fees
14 May - 15 May
The Burrell House

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is €163
includes taxes & fees
11 May - 12 May
The Carriage Barn Inn

Blooming Inn

Blooming Inn
3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (135 reviews)
"Beautiful comfortable home with many thoughtful touches"
United States
Rachel
The price is €138
includes taxes & fees
27 May - 28 May
Blooming Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"Pleasant stay!"
United States
Steven
The price is €88
includes taxes & fees
13 May - 14 May
The Putney Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (803 reviews)
"Staff were friendly and the breakfast was very good, great selection of items to choose from 🙂"
United States
Desiree
The price is €131
includes taxes & fees
29 May - 30 May
Comfort Inn & Suites Brattleboro I-91

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 €151
includes taxes & fees
13 May - 14 May
Inn at Valley Farms

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (877 reviews)
"Nice rooms, great downtown location, helpful staff...great value."
United States
Paul
The price is €129
includes taxes & fees
10 May - 11 May
Latchis Hotel

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 €233
includes taxes & fees
13 May - 14 May
The One Cat B&B

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,012 reviews)
"Excellent wedding venue"
United States
Ashley
The price is €136
includes taxes & fees
18 May - 19 May
The Colonial Hotel

The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (360 reviews)
"The serve breakfast on weekends and we were staying over Sunday night and the owner offered bagels and cereal and allowed me to take a cup of milk for coffee the next morning. Always an easy check in and very quiet, friendly, and clean. It's better than any other place in the area!"
United States
James G.
The price is €157
includes taxes & fees
10 May - 11 May
The Inn At Crumpin Fox

The Maguire House Bed & Breakfast

The Maguire House Bed & Breakfast
3.5 star property
Ashburnham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
United States
Ranjit
The price is €242
includes taxes & fees
13 May - 14 May
The Maguire House Bed & Breakfast

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is €442
includes taxes & fees
10 May - 11 May
Outdoor Adventure Hub! Family Home in West Dover

Gardner Inn

Gardner Inn
2.0 star property
Gardner
6.0 out of 10, (29 reviews)
"Great for a quick stay while passing through!"
United States
Cristen
The price is €85
includes taxes & fees
10 May - 11 May
Gardner Inn

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,007 reviews)
"The stay was great"
United States
Devon
The price is €142
includes taxes & fees
10 May - 11 May
Best Western Plus Keene Hotel

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, (1,005 reviews)
"Great stay "
United States
Rashida
The price is €129
includes taxes & fees
26 May - 27 May
Keene Elm City Hotel, an Ascend Collection Hotel
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

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.

Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

More cheap stays in Winchester

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.
What are some of the best holiday rentals that Winchester has to offer?
Lovely 2nd Floor Apartment: This holiday home rental outside of Winchester offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. See all 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 Barden State Wildlife Management Area, Rhododendron State Park and Cass Pond. A couple of additional sights to add to your itinerary are Winchester Speedpark and Pisgah State Park. 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.

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