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

Winchester Hotels from โ‚น8,787

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Centennial House

Centennial House
Northfield
United Kingdom
Alan
โ‚น15,845
โ‚น16,748 total
includes taxes & fees
25 Oct - 26 Oct
Centennial House

2. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Brattleboro
United States
Timothy
โ‚น14,049
โ‚น15,454 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG

3. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
Keene
United States
Ruddy
โ‚น13,437
โ‚น14,579 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Plus Keene Hotel

4. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
Keene
United States
Neil
โ‚น15,370
โ‚น16,677 total
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn & Suites Keene

5. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
Keene
United States
Christopher
โ‚น18,397
โ‚น19,960 total
includes taxes & fees
28 Oct - 29 Oct
Fairfield Inn & Suites by Marriott Keene Downtown

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
Keene
United States
Lisa
โ‚น12,056
โ‚น13,080 total
includes taxes & fees
25 Oct - 26 Oct
Keene Elm City Hotel, an Ascend Collection Hotel

7. Windmill Motel Restaurant

Windmill Motel Restaurant
Bernardston
United States
Donna
โ‚น10,835
โ‚น12,103 total
includes taxes & fees
3 Nov - 4 Nov
Windmill Motel Restaurant

8. The Inn At Crumpin Fox

The Inn At Crumpin Fox
Bernardston
United States
Heather
โ‚น10,679
โ‚น11,928 total
includes taxes & fees
1 Nov - 2 Nov
The Inn At Crumpin Fox

9. Latchis Hotel

Latchis Hotel
Brattleboro
United States
Erik
โ‚น13,456
โ‚น14,801 total
includes taxes & fees
1 Nov - 2 Nov
Latchis Hotel

10. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
Brattleboro
United States
Charlene
โ‚น10,618
โ‚น11,680 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Brattleboro I-91

11. Hampton Inn Brattleboro

Hampton Inn Brattleboro
Brattleboro
United States
Faith
โ‚น10,489
โ‚น11,538 total
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Brattleboro

12. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
Keene
United States
Deborah
โ‚น17,946
โ‚น19,471 total
includes taxes & fees
28 Oct - 29 Oct
Courtyard by Marriott Keene Downtown

13. Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield
United States
Thomas
โ‚น14,443
โ‚น15,671 total
includes taxes & fees
19 Nov - 20 Nov
Riverside Hotel, an Ascend Collection Hotel

14. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
Keene
United States
CHERYL
โ‚น8,795
โ‚น9,542 total
includes taxes & fees
25 Oct - 26 Oct
Days Inn by Wyndham Keene NH

15. Vikings Villages Resort

Vikings Villages Resort
Guilford
United States
Cecil
โ‚น17,786
โ‚น20,744 total
includes taxes & fees
22 Oct - 23 Oct
Vikings Villages Resort

16. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
โ‚น25,338
โ‚น27,871 total
includes taxes & fees
3 Nov - 4 Nov
Inn on Putney Road

17. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
โ‚น28,586
โ‚น31,016 total
includes taxes & fees
22 Oct - 23 Oct
Chesterfield Inn

18. The Carriage Barn Inn

The Carriage Barn Inn
Keene
United States
Richard
โ‚น14,099
โ‚น15,298 total
includes taxes & fees
27 Oct - 28 Oct
The Carriage Barn Inn

19. The Covered Bridge Inn

The Covered Bridge Inn
Brattleboro
United States
Adolfo
โ‚น9,967
โ‚น10,964 total
includes taxes & fees
22 Oct - 23 Oct
The Covered Bridge Inn

20. The Burrell House

The Burrell House
Keene
United States
Carol
โ‚น12,670
โ‚น14,127 total
includes taxes & fees
2 Nov - 3 Nov
The Burrell House
View all properties

Compare top hotels in Winchester

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

Centennial House

Northfield
View
A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro
View
A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

Best Western Plus Keene Hotel

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

Hampton Inn & Suites Keene

Keene
View
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

Keene
View
9.6
Exceptional
188 reviews
9.0
Wonderful
1,002 reviews
8.2
Very good
1,000 reviews
8.8
Excellent
426 reviews
8.8
Excellent
804 reviews
โ‚น15,845
โ‚น16,748 total
includes taxes & fees
25 Oct - 26 Oct
โ‚น14,049
โ‚น15,454 total
includes taxes & fees
8 Nov - 9 Nov
โ‚น13,437
โ‚น14,579 total
includes taxes & fees
1 Nov - 2 Nov
โ‚น15,370
โ‚น16,677 total
includes taxes & fees
19 Nov - 20 Nov
โ‚น18,397
โ‚น19,960 total
includes taxes & fees
28 Oct - 29 Oct
Save an average of 15% on thousands of hotels when you're signed in

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

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.
See properties

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 licence to fully enjoy this tranquil natural retreat.
See properties

New England Sweetwater Farm & Distillery

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

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.
See properties

Attleboro Mountain

Commune with nature and explore the great outdoors at Attleboro Mountain during your travels in Richmond.
See properties

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.
See properties

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.
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

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

8/10 Good
"Clean comfortable room with a comfortable bed. I didnโ€™t like the smell of whatever cleaning product they used, it was a bit bit strong let the kind you used to cover up something. Was this recently a smoking hotel? Also I missed an cycle in the fitness center, although the machines that were there seemed to work well. All in all itโ€™s about what you would expect for a moderately priced hotel in New Hampshire during leaf peeper season."
Judith 1-night trip
Posted 10 hours ago
Days Inn by Wyndham Keene NH
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The hotel was fairly new. Coffee was the only thing I felt needed changed."
Debbie 1-night trip
Posted 11 hours ago
Hampton Inn Brattleboro
Colonial Motel

Colonial Motel

8/10 Good
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."
Andrea 3-night trip
Posted 1 day ago
Colonial Motel
Deerfield Inn

Deerfield Inn

10/10 Excellent
"Great place to stay in ร  beautiful town! The staff were very accommodating and helpful. Would love to come back and explore more of Deerfield."
Melissa 1-night trip
Posted 1 day ago
Deerfield Inn
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"Excellent place to stay"
Matthew 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"This hotel is amazing. A relief to tired travelers. Clean, quiet, and friendly. And a good associated restaurant near by at the golf course. Very happy with our stay."
Sallie 1-night trip
Posted 2 days ago
The Inn At Crumpin Fox
The Putney Inn

The Putney Inn

10/10 Excellent
"Our room was quiet, clean and very comfortable. Breakfast was nice--more than enough for a decent breakfast before heading out-- waffle maker, toast, yogurt, cold cereal, fruit, juice coffee, and tea, etc. The grounds were beautiful and well kept. The staff was very helpful and parking was super easy right next to the room. The only slight downside was a strong musty odor in the entryway of the room (106), but the room itself smelled clean and was just fine."
Donna 1-night trip
Posted 2 days ago
The Putney Inn
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

8/10 Good
"Great location for access to southern VT and southwest NH, clean rooms, great views of river, and easy access from highway. No breakfast, but coffee bar provided. Free parking. Walls are a little thin."
Laura 3-night trip
Posted 2 days ago
Riverside Hotel, an Ascend Collection Hotel
The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"We love this hotel! We stay every year when we go to Wachusett Mountain"
Mollie 1-night trip
Posted 2 days ago
The Colonial Hotel

More cheap stays in Winchester

The Putney Inn

The Putney Inn

57 Putney Landing Rd Putney VT
โ‚น7,988
โ‚น8,787 total
25 Oct - 26 Oct
includes taxes & fees
The Putney Inn
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
โ‚น8,795
โ‚น9,542 total
25 Oct - 26 Oct
includes taxes & fees
7/10 Good! (1,003 reviews)
Days Inn by Wyndham Keene NH
Gardner Inn

Gardner Inn

22 Pearson Blvd Gardner MA
โ‚น10,081
โ‚น11,261 total
1 Nov - 2 Nov
includes taxes & fees
7.8/10 Good! (81 reviews)
Gardner Inn
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT
โ‚น10,618
โ‚น11,680 total
15 Nov - 16 Nov
includes taxes & fees
8.6/10 Excellent! (889 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
โ‚น12,056
โ‚น13,080 total
25 Oct - 26 Oct
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
โ‚น13,456
โ‚น14,801 total
1 Nov - 2 Nov
includes taxes & fees
Latchis Hotel

Find out more about Winchester

Historic charm and cultural delights await in Winchester

Winchester, located in Hampshire, is a picturesque town surrounded by stunning natural landscapes. With its serene lake, visitors can enjoy activities like canoeing, boating, and kayaking. The lush forests provide the perfect setting for relaxing walks and scenic views. Winchester also boasts a charming marina and port, where you can indulge in swimming and take in the beautiful scenery. The town is home to the prestigious University of Winchester and the iconic Winchester Cathedral, which attracts visitors from around the world. Whether it's a wedding or a peaceful stay, Winchester offers a delightful experience for all.

How to find great deals and cheap hotels in Winchester

  • Consider booking your stay during off-peak times, as prices for hotels and attractions may be lower. The months of May to July are a good option.
  • Use the search filters on Expedia's website to find the cheapest hotels in Winchester that meet your specific preferences and requirements.
  • Take advantage of any Rewards programs or loyalty schemes offered by Expedia to earn points and save on future bookings.
  • Compare prices and deals from different hotels in Winchester to ensure you get the best value for your money.
  • Consider staying in a hotel near the lake or marina to enjoy easy access to activities like canoeing, boating, swimming, and kayaking.
  • Explore the nearby forests and enjoy the beautiful scenery Winchester has to offer.
  • Don't forget to read reviews and ratings from other travelers to get an idea of the quality and service provided by the hotels in Winchester.
  • Keep an eye out for any special promotions or discounts on Expedia's website that can help you save even more on your accommodation in Winchester.

Discover the flavours of Winchester

Winchester is a culinary haven with a diverse range of local cuisine and unique dishes to tantalize your taste buds. Whether you're in the mood for traditional British fare or international flavours, this charming city has it all. Indulge in the highlights of Winchester's dining scene, where you can savor innovative dishes from world-class chefs, enjoy high-end high teas, and sip on sunset cocktails on rooftop terraces. For a truly unique experience, venture out to a Bedouin camp in the desert and feast on mouthwatering barbecue, or try Japanese-Cuban fusion cuisine with stunning views across the Corniche. Don't miss the opportunity to spot yachts at Yas Marina while enjoying a delightful brunch or dine in a revolving restaurant with spectacular vistas.

When it comes to popular restaurants in Winchester, there are several options to satisfy your cravings. Win Win Express offers delectable Asian cuisine, while The Rustic Table serves up European and North American dishes. Craving pizza? Head over to A1 Pizza for a taste of their delicious pies. Each restaurant brings its own culinary style and flavours, ensuring a memorable dining experience in Winchester. So, whether you're a local or a visitor, be sure to explore the city's vibrant restaurant scene and discover the culinary delights it has to offer.

Best time to go to Winchester

Winchester boasts a year-around average temperature of 7.7ยฐC, peaking at 20.9ยฐC in July, its warmest month, and dipping to an average low of -6.6ยฐC in January, the coolest. Rainfall averages at 92.3mm annually, with October seeing the heaviest showers and February being the driest month.

Monthcalendar iconTemperature (Celcius)temperature iconRainfall (mm)rain icon
January-6.675.7
February-4.769.3
March0.184.3
April7.185.9
May13.299.8
June18.299.1
July20.9109.0
August20.196.8
September15.796.8
October8.8110.5
November3.195.2
December-3.284.8

The Winchester info point: What you need to know

Category
Details
LocationWinchester, New Hampshire, United States of America
PopulationApproximately 4,340
LanguageEnglish
Time ZoneEastern Standard Time (EST)
ClimateHumid continental climate
AttractionsWinchester Historical Society Museum, Pisgah State Park, Cathedral of the Pines
Local CuisineNew England-style seafood, apple cider donuts
TransportationCar rental, taxi services

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.
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 19ยฐC, while the coldest months are January and February, with an average of -2ยฐC. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.

Explore a world of travel with Expedia