Photo by Donny Campos

Winchester Hotels

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Top 10 trending Winchester hotels

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1004)
"We have stayed at this property a few times and it is always a pleasant experience. "
The Colonial Hotel

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (411)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)

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

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 €166
includes taxes & fees
2 Sept - 3 Sept
The Carriage Barn Inn

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1002)
"Spacious, comfortable room in easy waking distance to many restaurants and shopping. Staff is warm and welcoming. "
The price is €169
includes taxes & fees
7 Aug - 8 Aug
Courtyard by Marriott Keene Downtown

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 €145
includes taxes & fees
24 Aug - 25 Aug
Fairfield Inn & Suites by Marriott Keene Downtown

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (132)
"Restful and relaxing "
The Burrell House

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1005)
"Great place!"
The price is €133
includes taxes & fees
24 Aug - 25 Aug
Best Western Plus Keene Hotel

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (322)
"Keene NH Hampton was probaly the nicest Hampton I ever stayed at. Clean & friendly "
The price is €147
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Keene

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (865)
"Good place to stop "
The price is €117
includes taxes & fees
10 Aug - 11 Aug
Keene Elm City Hotel, Ascend Hotel Collection

Days Inn by Wyndham Keene NH

2.0 star property
7.2 out of 10, Good, (1002)
"Great stay"
The price is €99
includes taxes & fees
24 Aug - 25 Aug
Days Inn by Wyndham Keene NH

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (158)
"Great breakfast, friendly staff"
The price is €165
includes taxes & fees
4 Aug - 5 Aug
Centennial House

Inn at Valley Farms

2.0 star property
10.0 out of 10, Exceptional, (9)
"Wonderful location and property"
The price is €167
includes taxes & fees
4 Aug - 5 Aug
Inn at Valley Farms

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 €164
includes taxes & fees
13 Aug - 14 Aug
The Inn At Crumpin Fox

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is €282
includes taxes & fees
4 Aug - 5 Aug
Chesterfield Inn

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (822)
"Great property and staff!"
The price is €147
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn & Suites Greenfield

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1007)
"Very enjoyable stay"
The Putney Inn

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (769)
"Great stay!"
The price is €137
includes taxes & fees
25 Aug - 26 Aug
Latchis Hotel

The One Cat B&B

2.5 star property
9.6 out of 10, Exceptional, (75)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The price is €192
includes taxes & fees
6 Aug - 7 Aug
The One Cat B&B

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 €142
includes taxes & fees
11 Aug - 12 Aug
Riverside Hotel, Ascend Hotel Collection
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.

Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

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.