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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)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel
The Covered Bridge Inn
Exterior detail

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1001)
"Was great for the price "
The Covered Bridge Inn
The Inn At Crumpin Fox
Front of property

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (308)
"Only place to stay if you’re playing Crumpin Fox CC. Perfect location for the course."
The price is P9,894
P11,052 total
includes taxes & fees
Aug 14 - Aug 15
The Inn At Crumpin Fox
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free daily on-the-go breakfast

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"The breakfast lady's were a hoot"
The price is P10,441
P11,485 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Best Western Plus Keene Hotel
1 bedroom, premium bedding, individually decorated

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very Good, (1005)
"Great place!"
The price is P8,233
P8,933 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Plus Keene Hotel
Black Mountain Inn
Front of property

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (449)
"Staff was friendly and helpful. Beds were comfortable, room was clean, comfortable, and quiet."
The price is P6,543
P7,198 total
includes taxes & fees
Aug 10 - Aug 11
Black Mountain Inn
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"Always a pleasure to stay at the Colonial"
The price is P8,143
P8,957 total
includes taxes & fees
Aug 5 - Aug 6
Colonial Motel And Spa
Riverside Hotel, Ascend Hotel Collection
Sundeck

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (584)
"It was like staying in a page of Better Homes & Gardens :)"
The price is P8,850
P9,602 total
includes taxes & fees
Aug 11 - Aug 12
Riverside Hotel, Ascend Hotel Collection
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (686)
"Quiet, comfortable and dog friendly. Pleasant host at check in"
The price is P4,136
P4,550 total
includes taxes & fees
Aug 5 - Aug 6
Travelodge by Wyndham Brattleboro VT
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Free daily on-the-go breakfast

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (410)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
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, (1001)
"Great stay"
The price is P6,180
P6,705 total
includes taxes & fees
Aug 24 - Aug 25
Days Inn by Wyndham Keene NH
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (664)
"Great place for a quick stay with my son on the way to Maine. "
The price is P8,035
P8,838 total
includes taxes & fees
Aug 3 - Aug 4
Comfort Inn & Suites Brattleboro I-91
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (107)
"Lovely Inn and very responsive and approachable staff. "
The price is P5,512
P8,432 total
includes taxes & fees
Aug 18 - Aug 19
Blooming Inn
Hampton Inn Brattleboro
Free breakfast

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very Good, (855)
"Great place for a quick over night stay. "
The price is P7,119
P7,831 total
includes taxes & fees
Sep 2 - Sep 3
Hampton Inn Brattleboro
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, (726)
"Friendly, helpful staff. Old hotel in good condition. "
The price is P9,015
P9,782 total
includes taxes & fees
Aug 24 - Aug 25
Fairfield Inn & Suites by Marriott Keene Downtown
Keene Elm City Hotel, Ascend Hotel Collection
Indoor pool

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very Good, (864)
"Good place to stop "
The price is P7,276
P7,895 total
includes taxes & fees
Aug 12 - Aug 13
Keene Elm City Hotel, Ascend Hotel Collection
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1003)
"Very enjoyable stay"
The Putney 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, (821)
"Great property and staff!"
The price is P8,850
P9,885 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (321)
"Keene NH Hampton was probaly the nicest Hampton I ever stayed at. Clean & friendly "
The price is P9,142
P9,919 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Keene
Latchis Hotel
Hiking

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (769)
"Great stay!"
The price is P8,376
P9,213 total
includes taxes & fees
Aug 25 - Aug 26
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

Top Winchester Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"This hotel is very clean, and has a really helpful staff. Good shower, strong wi-fi. All for a very reasonable price."
Doug 2-night trip
Posted 1 day ago
The Putney Inn

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 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, 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 Hampton Inn Brattleboro 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 Richmond Wildlife Manangement Area, Rhododendron State Park, and Ashuelot River. A couple of additional sights to add to your agenda are New England Sweetwater Farm & Distillery and Pisgah State Park. 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.