Photo by Donny Campos

Winchester Hotels from from S$137

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Check prices for these dates

Tonight
27 Mar - 28 Mar
Tomorrow
28 Mar - 29 Mar
This weekend
28 Mar - 30 Mar
Next weekend
4 Apr - 6 Apr

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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 S$369
includes taxes & fees
2 Apr - 3 Apr
The Maguire House Bed & Breakfast
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.6 out of 10, Excellent, (1076)
"All was great. "
The price is S$205
includes taxes & fees
1 Apr - 2 Apr
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, (384)
"Very comfortable and great location. Friendly and easy to work with!"
The price is S$231
includes taxes & fees
30 Mar - 31 Mar
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 S$221
includes taxes & fees
1 Apr - 2 Apr
Monadnock Inn
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (146)
"This is a great place to stay. Host, Joe, was very friendly and helpful. The room was clean and cozy , and nicely furnished. Common areas were very comfortable and welcoming. We will definitely come back! "
The price is S$225
includes taxes & fees
1 Apr - 2 Apr
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, (1042)
"Everything "
The price is S$196
includes taxes & fees
8 Apr - 9 Apr
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, (691)
"Great hotel, perfect location, but the bed was a little uncomfortable on my back. Otherwise very clean, very nicely set up and modern Convenient parking, bathroom new and very nicely renovated."
The price is S$208
includes taxes & fees
9 Apr - 10 Apr
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 S$216
includes taxes & fees
3 Apr - 4 Apr
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, (1075)
"During my work trip, this hotel was perfect for my needs. The on-site restaurant was amazing! If I lived nearby, I'd definitely visit regularly. The room was clean and well-equipped, making my stay very enjoyable."
The price is S$195
includes taxes & fees
2 Apr - 3 Apr
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (286)
"Everything was fine although I had no clue how to put on the TV which was disappointing. Also I did not think the bed was that comfortable and thought the sheets were not crisp enough and thought the bed clothes should have been changed. The desk crew were great and the breakfast was very good with a lot of choices. "
The price is S$202
includes taxes & fees
20 Apr - 21 Apr
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, (823)
"CONVENIENT LOCATION, EASY ACCESS TO ROADWAYS. "
The price is S$177
includes taxes & fees
27 Apr - 28 Apr
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, (995)
"The hotel is a bit outdated but for the price it was fine. If you are looking for a place to stay that is no frills but safe this is the place to stay. We were just traveling thru and just needed a place to get a good, quiet night of sleep and this fit the build. Front desk person was nice and friendly. We had no issues. Would stay here again when in the area."
The price is S$137
includes taxes & fees
8 Apr - 9 Apr
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 S$304
includes taxes & fees
8 Apr - 9 Apr
Centennial House
Inn at Valley Farms
Library

Inn at Valley Farms

2.0 star property
10.0 out of 10, Exceptional, (2)
"Wonderful location and property"
The price is S$216
includes taxes & fees
30 Mar - 31 Mar
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, (284)
"Crumpin Fox is a very friendly family run hotel"
The price is S$307
includes taxes & fees
30 Mar - 31 Mar
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 S$447
includes taxes & fees
4 Apr - 5 Apr
Chesterfield Inn
Hampton Inn & Suites Greenfield
Down duvets, desk, blackout curtains, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (781)
"Was on third floor and could hear people from their rooms loudly "
The price is S$209
includes taxes & fees
20 Apr - 21 Apr
Hampton Inn & Suites Greenfield
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1084)
"Great value for the money. Very clean and quiet. "
The price is S$137
includes taxes & fees
30 Mar - 31 Mar
The Putney Inn
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (722)
"Very comfortable and quiet. Well situated and perfect for a quick getaway. Staff was very friendly and helpful."
The price is S$192
includes taxes & fees
7 Apr - 8 Apr
Latchis Hotel
The One Cat B&B
Exterior detail

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 S$332
includes taxes & fees
9 Apr - 10 Apr
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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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 Hampton Inn Brattleboro and Comfort Inn & Suites Brattleboro I-91. 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. Hampton Inn Brattleboro 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 Ashuelot River, Barden State Wildlife Management Area and Rhododendron State Park. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery 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.