Winchester Hotels from €82 - Fully Refundable Options

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Our top choices for Winchester hotels

A windmill, a row of cabins, and a grassy field at night.

1. Windmill Motel Restaurant

Bernardston

Donna

includes taxes & fees

7 Nov - 8 Nov

A two-story house with a red door, green shutters, and a snow-covered front yard.

2. Centennial House

Northfield

Alan

includes taxes & fees

18 Nov - 19 Nov

The exterior of Latchis Hotel with a classic architectural style, large windows, and a prominent entrance.

3. Latchis Hotel

Brattleboro

Erik

includes taxes & fees

9 Nov - 10 Nov

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

4. The Inn At Crumpin Fox

Bernardston

Al

includes taxes & fees

22 Nov - 23 Nov

A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.

5. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Charlene

includes taxes & fees

22 Nov - 23 Nov

A hotel room with two beds, a TV, a desk, and a window with curtains.

6. Days Inn by Wyndham Keene NH

Keene

CHERYL

includes taxes & fees

8 Nov - 9 Nov

A stone fire pit with flames in front of a house with a covered porch and blue lighting.

7. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

includes taxes & fees

6 Dec - 7 Dec

A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.

8. Hampton Inn Brattleboro

Brattleboro

Faith

includes taxes & fees

15 Nov - 16 Nov

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

9. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Lisa

includes taxes & fees

8 Nov - 9 Nov

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

10. Best Western Plus Keene Hotel

Keene

Ruddy

includes taxes & fees

8 Nov - 9 Nov

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

11. Hampton Inn & Suites Keene

Keene

Dayle

includes taxes & fees

5 Dec - 6 Dec

A dock extending into a lake with a grassy area in the foreground and trees in the background.

12. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Steve

includes taxes & fees

6 Dec - 7 Dec

A hotel with a clock tower, a parking lot, and a well-maintained garden.

13. Black Mountain Inn

Brattleboro

Ron

includes taxes & fees

8 Nov - 9 Nov

A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.

14. Econo Lodge Brattleboro South

Brattleboro

Luis

includes taxes & fees

6 Dec - 7 Dec

A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.

15. The Covered Bridge Inn

Brattleboro

Rick

includes taxes & fees

5 Dec - 6 Dec

A reception area with a counter, a computer, and various informational posters on the wall.

16. Travelodge by Wyndham Brattleboro VT

Brattleboro

Cara

includes taxes & fees

8 Nov - 9 Nov

A historic brick building with a porch and a sign reading "Burrell House."

17. The Burrell House

Keene

Carol

includes taxes & fees

16 Nov - 17 Nov

A cozy living room with a fireplace, a coffee station, and a view of the outside.

18. Colonial Motel

Brattleboro

Swaraj

includes taxes & fees

8 Nov - 9 Nov

A hotel room with two beds, a desk, and a TV.

19. The Putney Inn

Putney

Kristen

includes taxes & fees

8 Nov - 9 Nov

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

20. The Carriage Barn Inn

Keene

Richard

includes taxes & fees

22 Nov - 23 Nov

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Stay near popular Winchester attractions

Winchester Speedpark

Winchester Speedpark thrills with professionally designed motocross tracks featuring challenging jumps and turns. Experience heart-pounding night races or watch competitors tackle the New England racing circuit.

See properties

Learn more about Winchester

Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic city centre district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester

A snow-covered bridge over a river with a red roof, surrounded by trees and buildings.

Top Winchester Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Great welcome, nice and convenient location. Clean, quiet, updated room with a comfortable bed."

Otherland Hotel

10/10 Excellent

"We had such a great stay at The Otherland Hotel and would absolutely give it a 10/10. Everything felt updated, modern, and very clean. The common areas were especially nice — comfortable and inviting, with a fireplace upstairs and a small kitchenette downstairs with a microwave, sink, and water dispenser, which was really convenient for warming up food. The bed and pillows were incredibly comfortable, and we loved being able to sit outside by the fire pit for a while. It was also perfect for traveling with our dog because she had plenty of room to run around in the fields. There are lots of thoughtful little touches throughout the hotel too, including board games and books in the common rooms for guests to enjoy. It felt cozy, relaxed, and very well cared for. We would definitely stay here again."

Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"A one-night stay. It had everything we needed. Not fancy, but it was all there, clean and bright. It is right next to the Interstate, but we could not hear any road traffic, so for the win. The morning breakfast scene is complete. The staff was very polite and accommodating."

More cheap stays in Winchester

The Putney Inn

57 Putney Landing Rd Putney VT

€82

8 Nov - 9 Nov

includes taxes & fees

Frequently asked questions

What's the best place to stay in Winchester?

Colonial Motel, located 11.5 mi (18.5 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 The Colonial Hotel and Latchis Hotel. See all available top hotels, or vacation rentals in Winchester.

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

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Winchester is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. 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: Offers a sauna, an indoor pool and free self parking. Keene Elm City Hotel, an Ascend Collection Hotel and Best Western Plus Keene Hotel 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 Birch Point, Cass Pond and Royalston State Forest. A couple of additional sights to add to your itinerary are Winchester Speedpark and New England Sweetwater Farm & Distillery. 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.

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Our top choices for Winchester hotels

1. Windmill Motel Restaurant

2. Centennial House

3. Latchis Hotel

4. The Inn At Crumpin Fox

5. Comfort Inn & Suites Brattleboro I-91

6. Days Inn by Wyndham Keene NH

7. Holiday Inn Express Hotel & Suites Brattleboro by IHG

8. Hampton Inn Brattleboro

9. Keene Elm City Hotel, an Ascend Collection Hotel

10. Best Western Plus Keene Hotel

11. Hampton Inn & Suites Keene

12. Riverside Hotel, an Ascend Collection Hotel

13. Black Mountain Inn

14. Econo Lodge Brattleboro South

15. The Covered Bridge Inn

16. Travelodge by Wyndham Brattleboro VT

17. The Burrell House

18. Colonial Motel

19. The Putney Inn

20. The Carriage Barn Inn

Stay near popular Winchester attractions

Winchester Speedpark

Learn more about Winchester

Top Winchester Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

More cheap stays in Winchester

The Putney Inn

Frequently asked questions

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