Photo by Donny Campos

Winchester Hotels from S$133

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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

Filter by

Guest rating
Guest rating
Property class

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$319
includes taxes & fees
27 Mar - 28 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 S$209
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 S$202
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 S$221
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 S$246
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)
"My don and I stayed one night. The location was good, room was spacious and clean."
The price is S$220
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 S$202
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 S$198
includes taxes & fees
26 Feb - 27 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 S$192
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 S$197
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 S$177
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 S$136
includes taxes & fees
9 Mar - 10 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 S$287
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 S$221
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 S$252
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 S$446
includes taxes & fees
26 Feb - 27 Feb
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, (773)
"One of the best places I stayed. Very beautiful place, great staff working there I was really impressed. Will be back!"
The price is S$228
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)
"I like the location. Convenient from where I live & very peaceful/quiet just to get away for a night. Front desk was courteous. "
The price is S$133
includes taxes & fees
3 Mar - 4 Mar
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 S$183
includes taxes & fees
3 Mar - 4 Mar
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)
"This is one of our favorite hotels to stay at."
The price is S$208
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.

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.