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

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Our top choices for Winchester 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 room with a fireplace, a standing heater, and a fan.
A red building with white trim, surrounded by lush greenery and fruit trees.

1. Centennial House

Centennial House
Northfield
United Kingdom
Alan
￥25,996
￥27,478 total
includes taxes & fees
Oct 11 - Oct 12
Centennial House
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.
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.
A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.

2. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Daniel
￥22,512
￥24,763 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Hotel & Suites Brattleboro by IHG
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 grassy area with picnic tables and a clock tower.
A room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.
A large, single-story building with a central entrance and a covered walkway.

3. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Donna
￥20,190
￥22,552 total
includes taxes & fees
Oct 4 - Oct 5
Windmill Motel Restaurant
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.
A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel room with a large bed, two smaller beds, a desk with a TV, a chair, and a view of the outdoors.
A covered outdoor area with a wooden deck, white railings, and string lights.

4. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
￥21,883
￥23,744 total
includes taxes & fees
Oct 25 - Oct 26
Best Western Plus Keene Hotel
A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.
A reception area with a 'Welcome to the Granite State' sign, a reception desk, and a well-organized suite shop.
An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.
A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

5. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
sheri
￥22,080
￥23,957 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Keene
A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.
An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.
A modern kitchen with wooden cabinets, a coffee machine, a fruit juice dispenser, and a refrigerator.
A hotel room with a bed, a desk, a chair, a wooden door, and a window.

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Kristin
￥18,892
￥20,498 total
includes taxes & fees
Nov 1 - Nov 2
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior
A bar area with a fireplace, seating, and a TV.
A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.
A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

7. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Caroline
￥30,510
￥33,103 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott Keene Downtown
A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.
A gazebo with a red roof and white walls, surrounded by trees and a brick building.
A brick building with a red awning and a sign that reads "The Inn."
A conference table set for a meeting with chairs and folded red napkins.

8. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Alan
￥17,711
￥19,783 total
includes taxes & fees
Nov 1 - Nov 2
The Inn At Crumpin Fox
A hotel lobby with a reception desk, two sofas, a coffee station, and a dining area.
A hotel room with a sofa, a coffee table, a chair, a desk, and a lamp.
A hotel room with a bed, a sofa, a desk, and a chair. There are three framed pictures on the wall.
An indoor swimming pool with a tiled deck, safety signs, and a few chairs.

9. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
John
￥17,583
￥19,340 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Brattleboro I-91
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 hotel lobby with a reception desk, seating area, and a large window.

10. Latchis Hotel

Latchis Hotel
Brattleboro
United States
jeffrey
￥28,182
￥31,001 total
includes taxes & fees
Oct 5 - Oct 6
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 compact hotel room with a kitchenette, a sofa, a small table, and a window with curtains.
A lobby with wooden paneling, a fireplace, and two green armchairs.

11. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Francesca
￥18,600
￥20,460 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Brattleboro
A dock extending into a lake with a grassy area in the foreground and trees in the background.
A spacious bedroom with a large bed, a desk, and a television.
A building with a large balcony overlooking a body of water, a bridge in the foreground, and trees with autumn foliage.
A spacious living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.

12. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Jason
￥23,953
￥25,989 total
includes taxes & fees
Nov 1 - Nov 2
Riverside Hotel, an Ascend Collection Hotel
A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.
A multi-story brick building with a sign reading "COURTYARD BY MARRIOTT".
A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.
An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.

13. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
United States
Deborah
￥29,762
￥32,292 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Keene Downtown
A hotel room with two beds, a TV, a desk, and a window with curtains.
A Days Inn with a brick facade, a central entrance, and a parking lot.
A hotel gym with treadmills, an elliptical, dumbbells, and a stationary bike.
A conference room with a black table, wooden chairs, a mounted TV, and a decorative mirror.

14. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
￥14,318
￥15,536 total
includes taxes & fees
Oct 27 - Oct 28
Days Inn by Wyndham Keene NH
A wooden cabin with a thatched roof, accessible via a wooden walkway with railings.
A wooden interior with a fireplace, a staircase, and a dining area.
A wooden log cabin with a snow-covered entrance and a wooden fence in a snowy forest.
A cozy room with a wooden wall, a red sofa, a small table with a bottle, a book, and a plant.

15. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Cecil
￥21,710
￥25,321 total
includes taxes & fees
Oct 25 - Oct 26
Vikings Villages Resort
A dining area with a table and four chairs, a painting of a covered bridge, and a painting of a red building.
A hotel room with two beds, a nightstand, a lamp, a painting of a cabin, and a door.
A multi-story motel with a parking lot, several vehicles parked, and a tree in the foreground.
A sign for The Covered Bridge Inn with a welcome message.

16. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
Kari
￥19,679
￥21,646 total
includes taxes & fees
Oct 4 - Oct 5
The Covered Bridge Inn
A wooden table set with plates, cutlery, and a folded napkin.
A corner room with wooden flooring, a wooden table, and four chairs. Large windows with curtains are visible, offering a view of a green landscape and a red deck outside.
A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.
A bench in front of an apple tree with ripe apples.

17. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Jonathan
￥22,056
￥23,931 total
includes taxes & fees
Oct 11 - Oct 12
The Carriage Barn Inn
A swimming pool area with lounge chairs and a sunbed, surrounded by windows and doors.
A hotel lobby with a red carpet, a reception desk, a sofa, and chairs.
A sunroom with large windows, a dining area with a table and chairs, and a sofa.
A hotel room with two beds, a nightstand, a lamp, and a chair.

18. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
Brattleboro
United States
David
￥15,656
￥17,222 total
includes taxes & fees
Nov 1 - Nov 2
Econo Lodge Brattleboro South
A historic brick building with a porch and a sign reading "Burrell House."
A bedroom with a large bed, a wooden desk, and three chairs. There are three windows with shutters.
A kitchen with a microwave, coffee maker, and a KUPPST refrigerator. There are two stools and a small shelf with a vase.
A hallway with a white radiator, a wooden staircase, and a door with decorative glass panels.

19. The Burrell House

The Burrell House
Keene
United States
Justin
￥21,553
￥24,032 total
includes taxes & fees
Oct 21 - Oct 22
The Burrell House
A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.
A cozy living room with a television, books, and a comfortable couch.
A garden with a sign reading "The One Cat" and various plants and flowers.
A wooden desk with a variety of books and pamphlets, a small tiger figurine, and a mirror reflecting the room.

20. The One Cat B&B

The One Cat B&B
Brattleboro
United States
marjie
￥47,229
￥51,952 total
includes taxes & fees
Oct 5 - Oct 6
The One Cat B&B
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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

New England Sweetwater Farm & Distillery

This rustic distillery crafts award-winning spirits using locally sourced ingredients. Sample their unique vodkas and whiskeys while learning about the distillation process in a warm space adorned with reclaimed wood.
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Cass Pond

This serene 54-acre pond in Richmond offers peaceful fishing for bass, pickerel, and perch. Bring your own gear and a valid New Hampshire fishing license to fully enjoy this tranquil natural retreat.
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Richmond Wildlife Manangement Area

This protected wilderness features diverse New Hampshire ecosystems across forests, wetlands, and meadows. Explore marked trails for wildlife viewing, especially during spring migration or autumn's foliage display.
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Attleboro Mountain

Commune with nature and explore the great outdoors at Attleboro Mountain during your travels in Richmond.
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Barden State Wildlife Management Area

This serene wildlife reserve in New Hampshire offers undisturbed natural landscapes for wildlife observation. Bring binoculars for spotting native species while exploring the peaceful trails during spring through fall.
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Loring Field

Explore the great outdoors at Loring Field, a lovely green space in Winchester. While you're in the area, stroll along the lakeside.
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Bennett Gorge

This secluded woodland trail winds alongside a brook to the remnants of an historic mill. Explore Richmond's industrial past while enjoying the tranquil sounds of flowing water and forest solitude.
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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 downtown 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

Colonial Motel

Colonial Motel

8/10 Good
"I love these kinds of motor lodges and I want them to keep improving and to succeed."
David 1-night trip
Posted 1 hour ago
Colonial Motel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Very nice staff and enjoyed my stay."
Charlene 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Brattleboro I-91
Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Nice place."
Nicolas 2-night trip
Posted 3 hours ago
Vikings Villages Resort
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Bed was more comfortable than most, shower was great and breakfast was good"
Angelo 1-night trip
Posted 13 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Putney Inn

The Putney Inn

10/10 Excellent
"Just needed the basics. Putney Inn delivered!"
Gregory 1-night trip
Posted 1 day ago
The Putney Inn
The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"Clean room, comfortable bed. Quiet, wooded area."
Christine 1-night trip
Posted 2 days ago
The Inn At Crumpin Fox
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

8/10 Good
"Breakfast was good. It was very pricey for such a town as Greenfield where I grew up. The shower/bathroom needs venting but it's probably structurally impossible"
Greg 2-night trip
Posted 3 days ago
Hampton Inn & Suites Greenfield
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The hotel was clean and it was quiet in my room. Staff were nice. It was conveniently located"
Lauren 2-night trip
Posted 4 days ago
Hampton Inn Brattleboro
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

10/10 Excellent
"I booked at the last minute for an unplanned visit and was pleasantly surprised by the accommodations for the price."
STEPHEN 2-night trip
Posted 5 days ago
Days Inn by Wyndham Keene NH

More cheap stays in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
￥13,248
￥14,574 total
Oct 25 - Oct 26
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
The Putney Inn
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
￥14,318
￥15,536 total
Oct 27 - Oct 28
includes taxes & fees
7/10 Good! (1,000 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
￥15,586
￥17,409 total
Oct 18 - Oct 19
includes taxes & fees
Gardner Inn
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
￥17,583
￥19,340 total
Nov 1 - Nov 2
includes taxes & fees
8.6/10 Excellent! (877 reviews)
Comfort Inn & Suites Brattleboro I-91
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH
￥18,892
￥20,498 total
Nov 1 - Nov 2
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Keene Elm City Hotel, an Ascend Collection Hotel
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
￥28,182
￥31,001 total
Oct 5 - Oct 6
includes taxes & fees
Latchis Hotel

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 traveler data. Other good options for your stay in 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 vacation rentals in Winchester?
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: Visitors like this Winchester vacation home rental. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
For more details about rescheduling or cancelling your trip to Winchester, go to https://www.expedia.com/service/.
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 two additional hotels with an onsite pool. View all hotels with pools in Winchester.
What is the best hotel near Hartness State Airport (VSF)?
The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.
What is staying in Winchester like?
Visitors to Winchester are sure to enjoy the lakeside setting. Tourists can also enjoy so much more including its forests. In Winchester, there are 6 hotels and other accommodations to choose from. Find out more about Winchester.
What should I do while I'm visiting Winchester?
Natural beauty is on display at Birch Point, Cass Pond, and Royalston State Forest. A couple of additional sights to add to your agenda are Winchester Speedpark and New England Sweetwater Farm & Distillery. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall.

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