A snow-covered town with a river running through it, surrounded by mountains and trees.

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Check availability on Winchester Historic Hotels

Tonight
Oct 10 - Oct 11
Tomorrow
Oct 11 - Oct 12
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Winchester historic hotels

A two-story house with a red door, green shutters, and a snow-covered front yard.
A group of women in formal attire standing in a garden with a house in the background.
A kitchenette with a refrigerator, a coffee station, and a fruit basket.
A red building with white trim, surrounded by lush greenery and fruit trees.

1. Centennial House

Centennial House
Northfield
United Kingdom
Alan
NT$5,730
NT$6,057 total
includes taxes & fees
Oct 13 - Oct 14
Centennial House
A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.
A flat-screen TV mounted on a wall displaying a streaming service interface.
A grassy area with picnic tables and a clock tower.
A large, single-story building with a central entrance and a covered walkway.

2. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Donna
NT$4,095
NT$4,574 total
includes taxes & fees
Oct 11 - Oct 12
Windmill Motel Restaurant
A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.
A conference table set for a meeting with chairs and folded red napkins.
A conference room with a long table, six chairs, a projector screen, and a brick wall.
A gazebo with a red roof and white walls, surrounded by trees and a brick building.

3. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Heather
NT$3,592
NT$4,012 total
includes taxes & fees
Nov 1 - Nov 2
The Inn At Crumpin Fox
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.
A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.
A spacious lobby with a large flat-screen TV, modern seating, and a large window with a cityscape view.

4. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Timothy
NT$4,438
NT$4,881 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express Hotel & Suites Brattleboro by IHG
The exterior of Latchis Hotel with a prominent entrance, large windows, and potted plants.
A banquet hall with round tables, chairs, and a staircase.
A lobby with a central circular platform, a statue, and a fountain. There are paintings on the walls and a staircase to the left.
A covered bridge with a stone foundation, surrounded by lush greenery and a well-maintained lawn.

5. Latchis Hotel

Latchis Hotel
Brattleboro
United Kingdom
Deborah
NT$4,526
NT$4,978 total
includes taxes & fees
Nov 8 - Nov 9
Latchis Hotel
A large indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.
A spacious lobby with a stone wall, a reception desk, and a large window.
A modern dining area with a large table and chairs, a kitchen in the background, and a stone accent wall.
A lobby with wooden paneling, a fireplace, and two green armchairs.

6. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Francesca
NT$3,582
NT$3,940 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Brattleboro
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.

7. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Angelo
NT$3,799
NT$4,122 total
includes taxes & fees
Nov 2 - Nov 3
Keene Elm City Hotel, an Ascend Collection Hotel
A hotel room with two beds, a TV, a desk, and a window with curtains.
A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.
A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.
A Days Inn with a brick facade, a central entrance, and a parking lot.

8. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
NT$2,959
NT$3,211 total
includes taxes & fees
Oct 25 - Oct 26
Days Inn by Wyndham Keene NH
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

9. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
NT$4,519
NT$4,903 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Keene Hotel
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.
A hotel lobby with a reception desk, seating area, and a wall with framed pictures.

10. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
NT$3,532
NT$3,885 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Brattleboro I-91
View all properties

Top Winchester Hotel Reviews

Colonial Motel

Colonial Motel

8/10 Good
"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."
Leonard 3-night trip
Posted 2 days ago
Colonial Motel
The Inn At Crumpin Fox

The Inn At Crumpin Fox

8/10 Good
"Lovely setting."
Kay 1-night trip
Posted 2 days ago
The Inn At Crumpin Fox
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

10/10 Excellent
"Staff was helpful and super friendly. Rooms were clean and looked recently renovated. Thank you for a great stay, highly recommended and will return."
Robert 2-night trip
Posted 2 days ago
Hampton Inn & Suites Greenfield
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"We had a one night stay recently. We were on the newly-renovated 4th floor, which was very nice. The room was very clean. We were there early, so we went to the 99 Restaurants bar that was right in front of the Comfort Inn. Check-in was easy and the staff were very pleasant. Room was very nice. We did have an issue with the television, but staff responded quickly and solved the issue. The free breakfast in the morning was very nice. Pancakes, waffles (with fruit toppings & syrup), bacon, breads, bagels and muffins, fresh fruit, cereals, yogurts. Many beverage options. A very nice selection! Staff was right there to replenish anything that was running low. Parking was plentiful, and right in front of the entrance. Check-out was fast and easy. I would highly recommend Comfort Inn & Suites!"
Lori 1-night trip
Posted 3 days ago
Comfort Inn & Suites Brattleboro I-91

Frequently asked questions

What can a history buff expect from a stay in Winchester?
The historical sites in Winchester are probably a big part of your travel plans. Why not appreciate the lakeside during your visit?
How many historically relevant hotels will I find in Winchester?
In Winchester, you'll find 6 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the top historical sites and other places to visit in Winchester?
Favorite places to visit include Winchester Speedpark, New England Sweetwater Farm & Distillery, and Birch Point. A couple of additional sights to add to your agenda are Pisgah State Park and Cass Pond.
What is a historic hotel like in Winchester?
Historic hotels give guests the opportunity to stay in a building that has been officially recognized with a national historic designation. Historic hotels throughout the world can take the form of stately homes, palaces or even lodges, old police stations or skyscrapers. These types of hotels in Winchester often preserve authentic characteristics like traditional architecture and period features in their public spaces or guestrooms.
What is the difference between a historic hotel and a heritage hotel?
The two are similar. "Historic hotel" is a term often used in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to place more significance on the architecture and building. A heritage hotel draws meaning mainly from the cultural value and how it influenced the community.
Do historic hotels in Winchester have modern facilities?
Yes, every effort is made to preserve the historic aspects and traditions, while interiors have safety features and modern conveniences. Visitors can expect the amenities from a contemporary hotel such as private rooms with updated bathroom facilities, heating and air conditioning, and free and fast Internet. When you book a historic hotel in Winchester, it doesn't mean you're choosing a place that's rundown or uncomfortable for guests.

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