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Winchester Hotels from S$107

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Check prices for these dates

Tonight
24 Jun - 25 Jun
Tomorrow
25 Jun - 26 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

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Top 10 trending Winchester hotels

The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1002)
"Great place, location is nice, Restaurant is great."
The Colonial Hotel
The Covered Bridge Inn
Concierge desk

The Covered Bridge Inn

2.5 star property
8.0 out of 10, Very good, (1005)
"Great stop on our trip"
The Covered Bridge Inn
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (297)
"Quiet clean hotel with no real amenities, but that can be a good thing. "
The price is S$272
includes taxes & fees
25 Jun - 26 Jun
The Inn At Crumpin Fox
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1006)
"After a big day it was nice to have this hotel so close. We slept really well and the breakfast was great. Would stay here again."
The price is S$187
includes taxes & fees
25 Jun - 26 Jun
Best Western Plus Keene Hotel
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Exterior

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (992)
"Clean, neat, good breakfast, quiet, and friendly staff. We had a perfect stay. "
The price is S$202
includes taxes & fees
3 Jul - 4 Jul
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Black Mountain Inn
Front of property

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (439)
"Courteous, helpful staff Convenient to highways and downtown Comfortable grounds Easy sleeping"
The price is S$170
includes taxes & fees
1 Jul - 2 Jul
Black Mountain Inn
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1010)
"Great place "
Colonial Motel And Spa
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (644)
"Beds were comfortable and Desk attendant was very nice "
The price is S$189
includes taxes & fees
26 Jun - 27 Jun
Comfort Inn & Suites Brattleboro I-91
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (676)
"I didn't like anything. The room smelled awful , was dirty , tub didn't work, outside was dirty too. My socks were filthy from walking around room. I didn't feel safe the bed was hard."
The price is S$107
includes taxes & fees
15 Jul - 16 Jul
Travelodge by Wyndham Brattleboro VT
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, (1002)
"Convenient to places to eat in shopping, easy to find. Friendly staff, easy check in. Decent shape of the building and clean in the rooms. "
The price is S$128
includes taxes & fees
29 Jun - 30 Jun
Days Inn by Wyndham Keene NH
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, (404)
"It was a beautiful place right off the main road where there were restaurants and shops and everything right within a 5 to 8 minute walk it was a beautiful place to stay"
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Hampton Inn Brattleboro
Lobby

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (838)
"We had a lovely trip thank you"
The price is S$179
includes taxes & fees
6 Jul - 7 Jul
Hampton Inn Brattleboro
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, (573)
"Clean, well decorated, comfortable and spacious rooms. Staff was very courteous and helpful. We will definitely come stay again. "
The price is S$212
includes taxes & fees
30 Jun - 1 Jul
Riverside Hotel, Ascend Hotel Collection
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, (721)
"We had a lovely stay. Decent breakfast, clean facilities. "
The price is S$198
includes taxes & fees
30 Jun - 1 Jul
Fairfield Inn & Suites by Marriott Keene Downtown
Hampton Inn & Suites Greenfield
Down duvets, desk, blackout curtains, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (810)
"very clean spacious, friendly staff, like newly renovated pool"
The price is S$219
includes taxes & fees
1 Jul - 2 Jul
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (307)
"We had a great time here! Clean rooms, polite staff and nice dinning area"
The price is S$206
includes taxes & fees
13 Jul - 14 Jul
Hampton Inn & Suites Keene
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (98)
"Great Place to stay in Small town"
The price is S$177
includes taxes & fees
7 Jul - 8 Jul
Blooming Inn
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1002)
"Quaint little Inn with spacious rooms and comfy beds. Just perfect and the guy at the front desk was super friendly and helpful! Would stay again if in the area "
The Putney Inn
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, (847)
"The hotel receptionist was very pleasant and helpful. "
The price is S$162
includes taxes & fees
1 Jul - 2 Jul
Keene Elm City Hotel, Ascend Hotel Collection
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (745)
"Our stay at the Latchis was wonderful! Super cool to be staying in an old art deco building, and we even took advantage of the movie theater a couple of times. Extremely conveniently located in the center of downtown, just a stone’s throw away from the Amtrak station. "
Latchis Hotel
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.

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 Rhododendron State Park, Ashuelot River and Cass Pond. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Winchester Speedpark. 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.