Photo by Donny Campos

Winchester Hotels

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Check prices for these dates

Tonight
24 Feb - 25 Feb
Tomorrow
25 Feb - 26 Feb
This weekend
28 Feb - 2 Mar
Next weekend
7 Mar - 9 Mar

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Top 10 trending Winchester hotels

The Maguire House Bed & Breakfast
Building design

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Terry was an amazing host. She was so hospitable and made my stay here that much more comfortable. She not only cooks really amazing breakfast but she was so helpful when I wanted to check out the town. Her house is really truly beautiful and the lake is a little walk away from the house. I highly recommend coming here."
The price is €253
includes taxes & fees
5 Mar - 6 Mar
The Maguire House Bed & Breakfast
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.6 out of 10, Excellent, (1009)
"This Hotel was much better then I expected. It’s beautiful, clean, staff is super attentive and friendly. Hotel is big and room as comfortable. My family and I had a great time. Highly recommend. If we ever go back to Massachusetts we will definitely stay at The Colonial Hotel again. "
The price is €149
includes taxes & fees
25 Feb - 26 Feb
The Colonial Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Front of property

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (375)
"The staff was wonderful and the property was super clean. Had a beautiful veiw of the river."
The price is €144
includes taxes & fees
25 Feb - 26 Feb
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (264)
"owners are very nice "
The price is €158
includes taxes & fees
25 Feb - 26 Feb
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (144)
"I was in town for the Harris Hill Ski Jump Challenge in Brattleboro, VT and decided to stay in Keene, NH a town I always wanted to visit. I couldn't have picked a better location. What a lovely place and a brisk 5-minute walk got me into town with a great bakery, running store and restaurants. I'll be back, so much more to do and see. Even got an afternoon of skiing in at Granite Gorge."
The price is €176
includes taxes & fees
25 Feb - 26 Feb
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, (1004)
"Parking is close to the hotel and incredibly convenient. The side doors are right next to the parking lot with easy access to your car. The staff is suoer friendly and helpful. "
The price is €158
includes taxes & fees
2 Mar - 3 Mar
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, (679)
"Wonderful and quiet! "
The price is €144
includes taxes & fees
2 Mar - 3 Mar
Fairfield Inn & Suites by Marriott Keene Downtown
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (123)
"We have a very sweet room that suits us fine. Is strange that we have not seen another person at this property since we have been here. No check in to speak of. Our friend is also staying here, and his room is essentially like a closet… so small. Close to town though, so very convenient"
The price is €141
includes taxes & fees
25 Feb - 26 Feb
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)
"Lori at the breakfast area is awesome! Happy, helpful & always so kind!!"
The price is €137
includes taxes & fees
2 Mar - 3 Mar
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (278)
"Always a great stay, rooms are very clean and the staff are friendly. "
The price is €141
includes taxes & fees
16 Mar - 17 Mar
Hampton Inn & Suites Keene
Holiday Inn Express Keene by IHG
Indoor pool

Holiday Inn Express Keene by IHG

2.5 star property
8.4 out of 10, Very good, (814)
"CONVENIENT LOCATION, EASY ACCESS TO ROADWAYS. "
The price is €127
includes taxes & fees
9 Mar - 10 Mar
Holiday Inn Express Keene by IHG
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (991)
"Clean and quiet:)"
The price is €97
includes taxes & fees
16 Mar - 17 Mar
Days Inn by Wyndham Keene NH
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (150)
"We had a great stay at Centennial House! Myself and my 14 year old son stayed for one night -- the bed was very comfortable and breakfast was fabulous!!"
The price is €205
includes taxes & fees
28 Feb - 1 Mar
Centennial House
Inn at Valley Farms
Library

Inn at Valley Farms

3.0 star property
The price is €158
includes taxes & fees
25 Feb - 26 Feb
Inn at Valley Farms
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (280)
"We enjoyed our stay very much."
The price is €181
includes taxes & fees
25 Feb - 26 Feb
The Inn At Crumpin Fox
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
The price is €319
includes taxes & fees
26 Feb - 27 Feb
Chesterfield Inn
Hampton Inn & Suites Greenfield
Room, 2 Queen Beds, Non Smoking

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (773)
"The motel was under construction, Not in the best area"
The price is €163
includes taxes & fees
23 Mar - 24 Mar
Hampton Inn & Suites Greenfield
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1004)
"The room is updated and clean"
The price is €97
includes taxes & fees
25 Feb - 26 Feb
The Putney Inn
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (714)
"Staff was accommodating and helpful. Room was basic, but that was expected due to the age of the building. Clean and sanitized, but definitely needed some “deep” cleaning, like dusting baseboards and taking marks off walls. Overall a good experience and in a great location. Would visit again!"
The price is €133
includes taxes & fees
25 Feb - 26 Feb
Latchis Hotel
Riverside Hotel, Ascend Hotel Collection
Select Comfort beds, in-room safe, desk, blackout curtains

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (559)
"Beautiful view "
The price is €149
includes taxes & fees
2 Mar - 3 Mar
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
Photo by Donny Campos
Open Photo by Donny Campos

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 Comfort Inn & Suites Brattleboro I-91. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck: This holiday home rental outside of Winchester offers a balcony, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 Comfort Inn & Suites Brattleboro I-91 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 6 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 Pisgah State Park, Rhododendron State Park and Ashuelot River. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Conant Public Library. 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.