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Check prices for these dates

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

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Top 10 trending Winchester hotels

Best Western Plus Keene Hotel
1 bedroom, premium bedding, individually decorated

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1002)
"Really enjoyed everything about my stay"
The price is €132
includes taxes & fees
24 Aug - 25 Aug
Best Western Plus Keene Hotel
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, (873)
"Staff were friendly, room clean and comfortable "
The price is €116
includes taxes & fees
18 Aug - 19 Aug
Keene Elm City Hotel, Ascend Hotel Collection
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, (1001)
"Great stay"
The price is €99
includes taxes & fees
24 Aug - 25 Aug
Days Inn by Wyndham Keene NH
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (325)
"Great hotel with friendly staff"
The price is €146
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Keene
The Covered Bridge Inn
Exterior detail

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1000)
"Was great for the price "
The price is €141
includes taxes & fees
5 Sept - 6 Sept
The Covered Bridge Inn
Hampton Inn & Suites Greenfield
Room, 2 Queen Beds, Non Smoking

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (823)
"Great property and staff!"
The price is €146
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn & Suites Greenfield
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1000)
"Very enjoyable stay"
The Putney Inn
Hampton Inn Brattleboro
Free breakfast

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (859)
"Great place for a quick over night stay. "
The price is €115
includes taxes & fees
4 Sept - 5 Sept
Hampton Inn Brattleboro
The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1000)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel
Latchis Hotel
Hiking

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (771)
"Great stay!"
The price is €131
includes taxes & fees
7 Sept - 8 Sept
Latchis Hotel
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 €123
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Brattleboro I-91
Monadnock Inn
Exterior

Monadnock Inn

2.5 star property
7.6 out of 10, Good, (265)
"It was very personable. They were very flexible with check-in. Quiet and homie. "
Monadnock Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (310)
"Excellent. Wonderful breakfast. "
The price is €148
includes taxes & fees
14 Aug - 15 Aug
Colonel Williams Inn
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (687)
"Quiet, comfortable and dog friendly. Pleasant host at check in"
The price is €67
includes taxes & fees
18 Aug - 19 Aug
Travelodge by Wyndham Brattleboro VT
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1001)
"Spacious, comfortable room in easy waking distance to many restaurants and shopping. Staff is warm and welcoming. "
The price is €176
includes taxes & fees
28 Aug - 29 Aug
Courtyard by Marriott Keene Downtown
Black Mountain Inn
Front of property

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (452)
"The bed was super comfortable and the sheets were very soft and also comfortable. "
The price is €106
includes taxes & fees
10 Aug - 11 Aug
Black Mountain Inn
The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (132)
"Restful and relaxing "
The Burrell House
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, (413)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
The Carriage Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

3.0 star property
9.6 out of 10, Exceptional, (153)
"Loved our stay. Beautifully decorated and I was able to play the house guitar in common room which was a unique touch I really enjoyed. Would gladly stay here again."
The price is €165
includes taxes & fees
3 Sept - 4 Sept
The Carriage Barn Inn
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1003)
"Always a pleasure to stay at the Colonial"
The price is €132
includes taxes & fees
17 Aug - 18 Aug
Colonial Motel And Spa
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

Blooming Inn

Blooming Inn

10/10 Excellent
"My daughter and I were looking for a safe and quiet place to stay while we were in the area for a night. I am so incredibly glad we chose Blooming Inn. From the moment we booked our room we felt welcome. Such a beautiful house with deep history. We will absolutely be back again!"
Courtnay 1-night trip
Posted 2 days ago
Blooming 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 traveller data. Two other choices for your trip to the area are Colonial Motel And Spa and Hampton Inn Brattleboro. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Lovely 2nd Floor Apartment: This holiday home rental outside of Winchester offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. See all 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 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 Richmond Wildlife Manangement Area, Rhododendron State Park and Ashuelot River. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Pisgah State Park. 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.