Photo by Donny Campos

Winchester hotels from RM471

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Top 10 trending Winchester hotels

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1002)
"Fantastic 9 day stay. Room (especially the bed) was very comfortable."
The Colonial Hotel

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (324)
"Clean room, extremely quiet with full occupancy, kind inkeeper."
The price is RM549
RM614 total
includes taxes & fees
2 Nov - 3 Nov
The Inn At Crumpin Fox

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1003)
"Good value for a two night stay for work "
The price is RM467
RM513 total
includes taxes & fees
8 Oct - 9 Oct
The Covered Bridge Inn

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (466)
"Excellent staff!"
The price is RM474
RM521 total
includes taxes & fees
2 Nov - 3 Nov
Black Mountain Inn

Gardner Inn

2.0 star property
5.0 out of 10, (8)
"The property needs work but hte staff was pleasant and the facility was quiet. "
The price is RM417
RM490 total
includes taxes & fees
2 Nov - 3 Nov
Gardner Inn

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1006)
"Would definitely stay again. Very convenient location "
The price is RM589
RM639 total
includes taxes & fees
3 Nov - 4 Nov
Best Western Plus Keene Hotel

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Good room, great breakfast options "
The price is RM796
RM875 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (606)
"The hotel is on a beautiful river front and the grounds are lovely. We drove to find dinner and it was easy enough. The hotel has a wonderful, helpful staff. "
The price is RM640
RM695 total
includes taxes & fees
27 Oct - 28 Oct
Riverside Hotel, an Ascend Collection Hotel

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (711)
"Horrible."
The price is RM432
RM475 total
includes taxes & fees
26 Oct - 27 Oct
Travelodge by Wyndham Brattleboro VT

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (427)
"Great price, close to town and really nice staff"
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (697)
"Check in was easy and there is coffee available 24 hours a day!"
The price is RM496
RM546 total
includes taxes & fees
2 Nov - 3 Nov
Comfort Inn & Suites Brattleboro I-91

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (798)
"Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. "
The price is RM587
RM646 total
includes taxes & fees
2 Nov - 3 Nov
Latchis Hotel

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1004)
"Nice place to stay for the night."
The price is RM589
RM648 total
includes taxes & fees
6 Oct - 7 Oct
Colonial Motel And Spa

Days Inn by Wyndham Keene NH

2.0 star property
7.0 out of 10, Good, (1003)
"Comfortable night stay. Would repeat "
The price is RM440
RM477 total
includes taxes & fees
4 Nov - 5 Nov
Days Inn by Wyndham Keene NH

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (895)
"Clean room and great breakfast"
The price is RM428
RM471 total
includes taxes & fees
5 Nov - 6 Nov
Hampton Inn Brattleboro

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (860)
"The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. "
The price is RM676
RM755 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Greenfield

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1001)
"Very enjoyable stay"
The Putney Inn

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very good, (911)
"the breakfast was good… rooms clean "
The price is RM451
RM489 total
includes taxes & fees
2 Nov - 3 Nov
Keene Elm City Hotel, an Ascend Collection Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (740)
"We stayed in the loft room and it was great! Right downtown, free parking right out the back and the staff is super nice. I would definitely go back!"
The price is RM690
RM749 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Keene Downtown

Vikings Villages Resort

2.0 star property
10.0 out of 10, Exceptional, (136)
"Favorite place to stay in New England bar none!! "
The price is RM914
RM1,066 total
includes taxes & fees
2 Nov - 3 Nov
Vikings Villages Resort
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

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

More cheap stays in Winchester

More cheap stays in Winchester

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 Keene Elm City Hotel, an Ascend Collection Hotel and Hampton Inn Brattleboro. 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. Keene Elm City Hotel, an Ascend Collection Hotel and Hampton Inn Brattleboro 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.

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