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Top hotels and accommodation in Winchester

The Maguire House Bed & Breakfast
Relax in a serene garden setting surrounded by lush foliage and vibrant flowers.

The Maguire House Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (34)
"Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. "
The price is NZ$455
includes taxes & fees
7 Aug - 8 Aug
The Maguire House Bed & Breakfast
The Colonial Hotel
Experience the grandeur of our lobby, featuring a beautifully patterned carpet, a comfortable seating area, and a stunning staircase.

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1012)
"Very good hotel "
The Colonial Hotel
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Enjoy cooking and brewing in this well-equipped kitchen with a coffee machine, coffee grinder, and refrigerator.

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (407)
"Clean, comfortable, easy check in/check out. Beautiful location, staff was friendly and efficient. "
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Monadnock Inn
Stroll up to this charming residence, featuring a covered porch with white columns and a small railing, surrounded by lush greenery.

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
Enjoy a meal with a view from this dining table near a window.

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 NZ$361
includes taxes & fees
28 July - 29 July
The Carriage Barn Inn
Courtyard by Marriott Keene Downtown
Check-in and check-out services are available at the central counter, with additional assistance offered at the smaller counters.

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1005)
"Spacious, comfortable room in easy waking distance to many restaurants and shopping. Staff is warm and welcoming. "
The price is NZ$306
includes taxes & fees
28 July - 29 July
Courtyard by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene Downtown
Classic architecture meets modern comfort at this inviting hotel entrance.

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (725)
"Friendly, helpful staff. Old hotel in good condition. "
The price is NZ$269
includes taxes & fees
17 Aug - 18 Aug
Fairfield Inn & Suites by Marriott Keene Downtown
The Burrell House
Traditional home with a covered front porch and garage, set amidst a beautifully landscaped yard.

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (131)
"Beautiful Inn!! Very happy customer ! I’ll be back !"
The Burrell House
Best Western Plus Keene Hotel
Welcome to Best Western PLUS, featuring a clean and modern exterior with a prominent logo and inviting entrance.

Best Western Plus Keene Hotel

3.0 star property
8.2 out of 10, Very good, (1004)
"Nice hotel "
The price is NZ$240
includes taxes & fees
29 July - 30 July
Best Western Plus Keene Hotel
Hampton Inn & Suites Keene
Welcome to the Granite State hotel, featuring a reception area and suite shop.

Hampton Inn & Suites Keene

2.5 star property
9.0 out of 10, Wonderful, (316)
"Keene NH Hampton was probaly the nicest Hampton I ever stayed at. Clean & friendly "
The price is NZ$270
includes taxes & fees
27 July - 28 July
Hampton Inn & Suites Keene
Keene Elm City Hotel, Ascend Hotel Collection
Relax by the pool surrounded by a spacious deck and lounge chairs.

Keene Elm City Hotel, Ascend Hotel Collection

2.5 star property
8.4 out of 10, Very good, (860)
"Good place to stop "
The price is NZ$210
includes taxes & fees
30 July - 31 July
Keene Elm City Hotel, Ascend Hotel Collection
Centennial House
Enjoy meals in a beautifully lit dining area with arched windows and a view of the outdoors.

Centennial House

3.5 star property
9.6 out of 10, Exceptional, (156)
"Great breakfast, friendly staff"
The price is NZ$262
includes taxes & fees
28 July - 29 July
Centennial House
Inn at Valley Farms
Relax in this inviting space with a large window, comfortable seating areas, and a classic design.

Inn at Valley Farms

2.0 star property
10.0 out of 10, Exceptional, (9)
"Wonderful location and property"
The price is NZ$275
includes taxes & fees
28 July - 29 July
Inn at Valley Farms
The Inn At Crumpin Fox
Welcome to The Inn at Crumpin-Fox, set amidst a beautiful landscaped area with vibrant tulips.

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (305)
"Very nice and very responsive staff"
The price is NZ$349
includes taxes & fees
13 Aug - 14 Aug
The Inn At Crumpin Fox
Chesterfield Inn
Cozy living room with a rustic fireplace, large windows, and classic furnishings.

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
The price is NZ$540
includes taxes & fees
30 July - 31 July
Chesterfield Inn
Hampton Inn & Suites Greenfield
Two beds with crisp linens, a desk with TV, microwave, and refrigerator, and a window with a view.

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (819)
"Great property and staff!"
The price is NZ$328
includes taxes & fees
10 Aug - 11 Aug
Hampton Inn & Suites Greenfield
The Putney Inn
Welcome to The Putney Inn, a restaurant and motel with a warm and inviting sign.

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1010)
"Certainly convenient, right off 91."
The Putney Inn
Latchis Hotel
Cross a historic bridge surrounded by lush greenery and a well-manicured lawn.

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (761)
"Great location, amazing history and architecture."
The price is NZ$238
includes taxes & fees
28 July - 29 July
Latchis Hotel
The One Cat B&B
Stroll through the serene garden, surrounded by vibrant blooms and a whimsical cat-themed sign.

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 NZ$349
includes taxes & fees
30 July - 31 July
The One Cat B&B
Riverside Hotel, Ascend Hotel Collection
Relax on the lakeside dock, surrounded by lush greenery and a tranquil atmosphere.

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (580)
"Great hotel experience from the moment we checked in. The service was excellent, hotel and rooms were so clean, and the sleep number bed was the best! It's a gem of a hotel! "
The price is NZ$273
includes taxes & fees
20 Aug - 21 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.

See all hotels in Winchester
Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"The room was very clean, staff was wonderful and check in and out was quick. I will definitely stay with you next year for Hillfest 2026."
Diane 1-night trip
Posted 3 days ago
The Colonial Hotel

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 Winchester Speedpark 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.