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24 Jul - 25 Jul
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25 Jul - 27 Jul
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Compare 415 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Maguire House Bed & Breakfast
Property grounds

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is SAR 1,032
SAR 1,032 total
includes taxes & fees
30 Jul - 31 Jul
The Maguire House Bed & Breakfast
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1012)
"Very good hotel "
The Colonial Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Free daily on-the-go breakfast

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (407)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is SAR 754
SAR 818 total
includes taxes & fees
27 Jul - 28 Jul
The Carriage Barn Inn
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1005)
"Spacious, comfortable room in easy waking distance to many restaurants and shopping. Staff is warm and welcoming. "
The price is SAR 634
SAR 688 total
includes taxes & fees
31 Jul - 1 Aug
Courtyard by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (725)
"Friendly, helpful staff. Old hotel in good condition. "
The price is SAR 563
SAR 611 total
includes taxes & fees
10 Aug - 11 Aug
Fairfield Inn & Suites by Marriott Keene Downtown
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (131)
"Beautiful Inn!! Very happy customer ! I’ll be back !"
The Burrell House
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very Good, (1004)
"Nice hotel "
The price is SAR 503
SAR 545 total
includes taxes & fees
30 Jul - 31 Jul
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (316)
"Keene NH Hampton was probaly the nicest Hampton I ever stayed at. Clean & friendly "
The price is SAR 561
SAR 608 total
includes taxes & fees
27 Jul - 28 Jul
Hampton Inn & Suites Keene
Keene Elm City Hotel, Ascend Hotel Collection
Indoor pool

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very Good, (861)
"Good place to stop "
The price is SAR 436
SAR 473 total
includes taxes & fees
31 Jul - 1 Aug
Keene Elm City Hotel, Ascend Hotel Collection
Centennial House
Free daily full breakfast

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (156)
"Great breakfast, friendly staff"
The price is SAR 542
SAR 573 total
includes taxes & fees
28 Jul - 29 Jul
Centennial House
Inn at Valley Farms
Library

Inn at Valley Farms

2.0 star property
10.0 out of 10, Exceptional, (9)
"Wonderful location and property"
The price is SAR 571
SAR 620 total
includes taxes & fees
27 Jul - 28 Jul
Inn at Valley Farms
The Inn At Crumpin Fox
Front of property

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (305)
"Very nice and very responsive staff"
The price is SAR 641
SAR 717 total
includes taxes & fees
7 Aug - 8 Aug
The Inn At Crumpin Fox
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is SAR 1,130
SAR 1,226 total
includes taxes & fees
30 Jul - 31 Jul
Chesterfield Inn
Hampton Inn & Suites Greenfield
Room, 2 Queen Beds, Non Smoking | Down comforters, desk, blackout drapes, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (819)
"Great property and staff!"
The price is SAR 663
SAR 741 total
includes taxes & fees
10 Aug - 11 Aug
Hampton Inn & Suites Greenfield
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1010)
"Certainly convenient, right off 91."
The Putney Inn
Latchis Hotel
Hiking

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (761)
"Great location, amazing history and architecture."
The price is SAR 502
SAR 553 total
includes taxes & fees
29 Jul - 30 Jul
Latchis Hotel
The One Cat B&B
Exterior

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is SAR 714
SAR 786 total
includes taxes & fees
30 Jul - 31 Jul
The One Cat B&B
Riverside Hotel, Ascend Hotel Collection
Sundeck

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (580)
"Great hotel experience from the moment we checked in. The service was excellent, hotel and rooms were so clean, and the sleep number bed was the best! It's a gem of a hotel! "
The price is SAR 571
SAR 619 total
includes taxes & fees
28 Jul - 29 Jul
Riverside Hotel, Ascend Hotel Collection
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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Learn more about Winchester

Get away to relaxing Winchester! Enjoy the lake views, forests, and more.

See all hotels in Winchester
The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.
Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Christine greeted me personally and reached out afterwards to learn about my experience. Love, love, love this place and can't wait to stay again!"
Gloria 1-night trip
Posted 22 hours ago
Vikings Villages Resort

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 traveler data. Other good options for your stay in 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 vacation rentals in Winchester?

Lovely 2nd Floor Apartment: Visitors like this Winchester vacation home rental. It 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, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.

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 two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is the best hotel near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Winchester like?

Visitors to Winchester are sure to enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodations to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Natural beauty is on display at Richmond Wildlife Manangement Area, Rhododendron State Park, and Ashuelot River. A couple of additional sights to add to your agenda are Winchester Speedpark and Pisgah State Park. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.