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

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Check prices for these dates

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

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Our top choices for Winchester hotels

Lobby

1. Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,001 reviews)
"All the staff were very helpful and friendly! Truly enjoyed my stay"
United States
Ramica
The price is ļæ„21,547
ļæ„23,378 total
includes taxes & fees
Aug 9 - Aug 10
Keene Elm City Hotel, an Ascend Collection Hotel
Restaurant

2. Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,000 reviews)
"Staff was very friendly, accommodating, and attentive to our needs. Room was clean and comfortable!"
United States
Helen
The price is ļæ„23,782
ļæ„25,804 total
includes taxes & fees
Aug 9 - Aug 10
Best Western Plus Keene Hotel
Lobby

3. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,003 reviews)
"One of our favorite hotels in Brattleboro. Clean, safe and the staff are super friendly."
United States
Marnie
The price is ļæ„27,613
ļæ„30,374 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express Hotel & Suites Brattleboro by IHG
In-room safe, desk, blackout drapes, iron/ironing board

4. Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH
2.0 star property
Keene
7.0 out of 10, Good, (1,000 reviews)
"The hotel was clean but very dated. Needs new flooring, paint etc. Staff was very nice."
United States
Pamela
The price is ļæ„14,922
ļæ„16,190 total
includes taxes & fees
Aug 5 - Aug 6
Days Inn by Wyndham Keene NH
Deluxe Room, 1 Queen Bed, Valley View | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

5. Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
9.0 out of 10, Wonderful, (38 reviews)
"Wonderful experience at the Windmill Motel. I highly recommend!"
United States
Crystal
The price is ļæ„19,392
ļæ„21,660 total
includes taxes & fees
Aug 3 - Aug 4
Windmill Motel Restaurant
Lobby

6. Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (840 reviews)
"Staff wasfriendly and my room is very clean"
United States
Michael
The price is ļæ„20,805
ļæ„22,886 total
includes taxes & fees
Aug 26 - Aug 27
Comfort Inn & Suites Brattleboro I-91
Free daily buffet breakfast

7. Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (397 reviews)
"We spent 3 days there and totally enjoyed our stay in Keene, New Hampshire."
United States
Debra
The price is ļæ„24,082
ļæ„26,129 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn & Suites Keene
Indoor pool

8. Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very Good, (1,001 reviews)
"Really great spot for the price, very happy with our short stay."
United States
Kyle
The price is ļæ„20,740
ļæ„22,814 total
includes taxes & fees
Aug 24 - Aug 25
Hampton Inn Brattleboro
Seasonal outdoor pool

9. Econo Lodge Brattleboro South

Econo Lodge Brattleboro South
2.0 star property
Brattleboro
5.2 out of 10, (665 reviews)
"Quiet and clean place to stay the night"
United States
Aigul
The price is ļæ„13,431
ļæ„14,773 total
includes taxes & fees
Aug 31 - Sep 1
Econo Lodge Brattleboro South
Front of property

10. Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (217 reviews)
"Fantastic, beautiful property. We definitely want to visit again. Great for families."
United States
Otgonzaya
The price is ļæ„28,289
ļæ„32,993 total
includes taxes & fees
Aug 25 - Aug 26
Vikings Villages Resort
Exterior

11. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
"For the price it was not bad at all."
United States
Carolina
The price is ļæ„18,011
ļæ„19,812 total
includes taxes & fees
Aug 11 - Aug 12
The Putney Inn
Lobby

12. Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
6.8 out of 10, (29 reviews)
"Clean room ez checkin, coffee at breakfast good!"
United States
James
The price is ļæ„12,210
ļæ„13,431 total
includes taxes & fees
Aug 4 - Aug 5
Colonial Motel
Reception

13. Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (789 reviews)
"Good value!"
United States
Brian
The price is ļæ„11,779
ļæ„12,957 total
includes taxes & fees
Aug 4 - Aug 5
Travelodge by Wyndham Brattleboro VT
Free daily continental breakfast

14. The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.4 out of 10, Good, (1,000 reviews)
"The staff is so helpful and kind. There are sketchy people out there but overall the stay we are safe and we were able to sleep and rest."
United States
VINCENT JOEL
The price is ļæ„11,629
ļæ„12,793 total
includes taxes & fees
Aug 16 - Aug 17
The Covered Bridge Inn
Exterior

15. Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (942 reviews)
"Very nice boutique hotel. Close to everything. Staff was really well at check in and out. Definitely would go back"
United States
Donald
The price is ļæ„18,748
ļæ„20,622 total
includes taxes & fees
Aug 25 - Aug 26
Latchis Hotel
Exterior

16. The Inn At Crumpin Fox

The Inn At Crumpin Fox
2.5 star property
Bernardston
9.2 out of 10, Wonderful, (378 reviews)
"Fantastic breakfast!"
United States
allisha
The price is ļæ„25,921
ļæ„28,954 total
includes taxes & fees
Aug 9 - Aug 10
The Inn At Crumpin Fox
Exterior

17. Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (788 reviews)
"My favorite hotel!!!!"
United States
Brian
The price is ļæ„25,641
ļæ„27,821 total
includes taxes & fees
Aug 11 - Aug 12
Fairfield Inn & Suites by Marriott Keene Downtown
Pub

18. Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.6 out of 10, Excellent, (1,000 reviews)
"Staff was helpful and friendly. Room was clean, quiet and had a comfortable bed. Thank you for a pleasant stay."
United States
Nancy
The price is ļæ„28,658
ļæ„31,094 total
includes taxes & fees
Aug 18 - Aug 19
Courtyard by Marriott Keene Downtown
Front of property

19. Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (499 reviews)
"I had a wonderful stay. The pool was great and I had it to myself! My room was clean. I would definitely recommend!"
United States
Robert
The price is ļæ„25,255
ļæ„27,781 total
includes taxes & fees
Aug 4 - Aug 5
Black Mountain Inn
Free daily continental breakfast

20. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (175 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is ļæ„21,458
ļæ„23,282 total
includes taxes & fees
Aug 5 - Aug 6
The Carriage Barn Inn
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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Stay near popular Winchester attractions

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.
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 downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products.

See all hotels in Winchester
A snow-covered town with a river running through it, surrounded by mountains and trees.

Top Winchester Hotel Reviews

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"Nice property, well maintained and friendly staff. It would be nice to have coffee more prominently featured (and a snack or two?)"
sara 1-night trip
Posted 23 hours ago
Riverside Hotel, an Ascend Collection Hotel

More cheap stays in Winchester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH
The price is ļæ„14,922 per night from Aug 5 to Aug 6
ļæ„14,922
ļæ„16,190 total
Aug 5 - Aug 6
includes taxes & fees
7/10 Good! (1,000 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
2 private mountain RV pads for rent. Full hook ups, located 2.1 mi (3.5 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 Keene Elm City Hotel, an Ascend Collection Hotel and The Colonial Hotel. See all available top hotels, or vacation rentals in Winchester.
What are some of the best vacation rentals in Winchester?
Peaceful and relaxing cottage steps from Forest Lake.: Visitors give good reviews to this Winchester vacation home rental, which offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games. 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?
Keene Elm City Hotel, an Ascend Collection Hotel: Features buffet, an indoor pool, and complimentary wired internet access. The Colonial 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 7 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 Cass Pond, Royalston State Forest, and Rhododendron State Park. A couple of additional sights to add to your agenda are New England Sweetwater Farm & Distillery and Conant Public Library. 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 67Ā°F, while the coldest months are January and February with an average of 28Ā°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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