Photo by Donny Campos

Winchester Hotels

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Jul 9 - Jul 10
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Jul 10 - Jul 11
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Jul 11 - Jul 13
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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, (1007)
"Great motel "
The Colonial Hotel
The Inn At Crumpin Fox
Terrace/patio

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (302)
"Very nice and very responsive staff"
The price is P10,708
P11,961 total
includes taxes & fees
Jul 10 - Jul 11
The Inn At Crumpin Fox
The Covered Bridge Inn
Concierge desk

The Covered Bridge Inn

2.5 star property
8.0 out of 10, Very Good, (1000)
"Great stop on our trip"
The Covered Bridge Inn
Best Western Plus Keene Hotel
Exterior

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very Good, (1000)
"Nice hotel "
The price is P7,553
P8,195 total
includes taxes & fees
Jul 13 - Jul 14
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, (995)
"The nicest Holiday Inn Express I have ever stayed at. Lovely place and super clean."
The price is P9,424
P10,366 total
includes taxes & fees
Jul 13 - Jul 14
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, (442)
"Courteous, helpful staff Convenient to highways and downtown Comfortable grounds Easy sleeping"
The price is P6,696
P7,366 total
includes taxes & fees
Jul 17 - Jul 18
Black Mountain Inn
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1005)
"Great place "
The price is P5,529
P6,082 total
includes taxes & fees
Jul 10 - Jul 11
Colonial Motel And Spa
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (682)
"Quiet, comfortable and dog friendly. Pleasant host at check in"
The price is P4,514
P4,966 total
includes taxes & fees
Jul 13 - Jul 14
Travelodge by Wyndham Brattleboro VT
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 P8,114
P8,925 total
includes taxes & fees
Jul 13 - Jul 14
Comfort Inn & Suites Brattleboro I-91
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1004)
"Great stay"
The price is P5,222
P5,666 total
includes taxes & fees
Jul 16 - Jul 17
Days Inn by Wyndham Keene NH
Riverside Hotel, Ascend Hotel Collection
Select Comfort beds, in-room safe, desk, blackout drapes

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 P8,576
P9,305 total
includes taxes & fees
Jul 22 - Jul 23
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, (724)
"We had a lovely stay. Decent breakfast, clean facilities. "
The price is P8,004
P8,684 total
includes taxes & fees
Jul 27 - Jul 28
Fairfield Inn & Suites by Marriott Keene Downtown
Hampton Inn Brattleboro
Lobby

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very Good, (842)
"Great for the price"
The price is P7,138
P7,852 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn Brattleboro
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)
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 P5,610
P8,465 total
includes taxes & fees
Jul 10 - Jul 11
Blooming Inn
Hampton Inn & Suites Greenfield
Down comforters, desk, blackout drapes, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (813)
"Excellent service "
The price is P10,087
P11,268 total
includes taxes & fees
Aug 7 - Aug 8
Hampton Inn & Suites Greenfield
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 P8,334
P9,043 total
includes taxes & fees
Jul 20 - Jul 21
Hampton Inn & Suites Keene
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1000)
"Clean rooms with good parking. Minor complaint: breakfasts were a little sparse"
The Putney Inn
Keene Elm City Hotel, Ascend Hotel Collection
In-room safe, desk, iron/ironing board, free cribs/infant beds

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very Good, (854)
"Friendly staff and clean, spacious room. Breakfast was very good!! "
The price is P6,544
P7,100 total
includes taxes & fees
Jul 15 - Jul 16
Keene Elm City Hotel, Ascend Hotel Collection
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (755)
"Great location, amazing history and architecture."
The price is P7,355
P8,091 total
includes taxes & fees
Jul 13 - Jul 14
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 traveler data. Other good options for your stay in the area are Colonial Motel And Spa and Best Western Plus Keene Hotel. 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, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.

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 two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is the best hotel near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Winchester like?

Visitors to Winchester are sure to enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodations to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

Natural beauty is on display at Birch Point, Rhododendron State Park, and Ashuelot River. A couple of additional sights to add to your agenda are Pisgah State Park and New England Sweetwater Farm & Distillery. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.