Photo by Donny Campos

Winchester Hotels from S$126

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Winchester hotels

Vikings Villages Resort
2 bedrooms, premium bedding, down duvets, in-room safe

Vikings Villages Resort

2.0 star property
10.0 out of 10, Exceptional, (106)
"Loved the place! "
The price is S$334
includes taxes & fees
10 Jul - 11 Jul
Vikings Villages Resort
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (301)
"Very nice and very responsive staff"
The price is S$270
includes taxes & fees
8 Jul - 9 Jul
The Inn At Crumpin Fox
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1006)
"Great motel "
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, (406)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
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, (574)
"Clean, well decorated, comfortable and spacious rooms. Staff was very courteous and helpful. We will definitely come stay again. "
The price is S$210
includes taxes & fees
10 Jul - 11 Jul
Riverside Hotel, Ascend Hotel Collection
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (103)
"Great stay"
The price is S$416
includes taxes & fees
8 Jul - 9 Jul
Chesterfield Inn
Green River Bridge Inn
Exterior

Green River Bridge Inn

3.0 star property
10.0 out of 10, Exceptional, (1)
"Such a peaceful, beautiful area and inn! The host is wonderful and an amazing cook. The quintessential Vermont inn with an international flair. Can’t wait to go back!"
The price is S$281
includes taxes & fees
8 Jul - 9 Jul
Green River Bridge Inn
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1002)
"Nice hotel "
The price is S$185
includes taxes & fees
8 Jul - 9 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, (311)
"We had a great time here! Clean rooms, polite staff and nice dinning area"
The price is S$204
includes taxes & fees
13 Jul - 14 Jul
Hampton Inn & Suites Keene
Inn at Valley Farms
Library

Inn at Valley Farms

2.0 star property
10.0 out of 10, Exceptional, (8)
"Wonderful location and property"
The price is S$216
includes taxes & fees
10 Jul - 11 Jul
Inn at Valley Farms
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (130)
"Well maintained property with beautifully decorated rooms. "
The Burrell House
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (101)
"Great Place to stay in Small town"
The price is S$175
includes taxes & fees
9 Jul - 10 Jul
Blooming Inn
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$300
includes taxes & fees
9 Jul - 10 Jul
The One Cat B&B
Centennial House
Exterior detail

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (154)
"It was a unique property for New England being built in 1800 so I was pleasantly surprised that my only complaint was hot water. That’s pretty common in a building that old. I was not disappointed at all and enjoyed my stay greatly."
The price is S$204
includes taxes & fees
14 Jul - 15 Jul
Centennial House
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (650)
"Beds were comfortable and Desk attendant was very nice "
The price is S$189
includes taxes & fees
10 Jul - 11 Jul
Comfort Inn & Suites Brattleboro I-91
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (307)
"The inn keepers are always super friendly and the place is kept well. The breakfast is delicious. Great for families who prefer quiet and quaint."
The price is S$190
includes taxes & fees
10 Jul - 11 Jul
Colonel Williams Inn
Hampton Inn Brattleboro
Lobby

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (841)
"Great for the price"
The price is S$178
includes taxes & fees
13 Jul - 14 Jul
Hampton Inn Brattleboro
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (754)
"Great location, amazing history and architecture."
The price is S$168
includes taxes & fees
13 Jul - 14 Jul
Latchis Hotel
The Inn At Quail Run
Seasonal outdoor pool

The Inn At Quail Run

2.5 star property
9.0 out of 10, Wonderful, (64)
"Exceptional service beautiful place "
The price is S$301
includes taxes & fees
21 Jul - 22 Jul
The Inn At Quail Run
Keene Elm City Hotel, Ascend Hotel Collection
In-room safe, desk, iron/ironing board, free cots/infant beds

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (852)
"Friendly staff and clean, spacious room. Breakfast was very good!! "
The price is S$160
includes taxes & fees
13 Jul - 14 Jul
Keene Elm City 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.
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 Days Inn by Wyndham Keene NH. 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 Best Western Plus Keene Hotel 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 Rhododendron State Park, Ashuelot River and Cass Pond. A couple of additional sights to add to your itinerary are Pisgah State Park and New England Sweetwater Farm & Distillery. 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.