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Check prices for these dates

Tonight
24 Mar - 25 Mar
Tomorrow
25 Mar - 26 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

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Our top choices for Winchester hotels

Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (786 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is ฿4,559
฿5,014 total
includes taxes & fees
27 Mar - 28 Mar
Comfort Inn & Suites Brattleboro I-91
Interior

The Colonial Hotel

The Colonial Hotel
3.0 star property
Gardner
8.8 out of 10, Excellent, (1,008 reviews)
"Great staff, great food, clean, friendly"
United States
Thomas
The Colonial Hotel
Restaurant

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)
"Great stay pool was very nice"
United States
Patrick
The price is ฿4,827
฿5,238 total
includes taxes & fees
26 Mar - 27 Mar
Best Western Plus Keene Hotel
Standard Room, 2 Queen Beds, Refrigerator & Microwave | Desk, iron/ironing board, rollaway beds, free WiFi

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
"Great Stay!"
United States
Nicholas
The Putney Inn
Lobby

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, (999 reviews)
"Clean room, polite staff,kids enjoyed the indoor heated pool they also have a small gym and breakfast in the morning couldn't beat the price definitely a great place for the family dogs are also welcome!!"
United States
Sean
The price is ฿4,082
฿4,429 total
includes taxes & fees
14 Apr - 15 Apr
Keene Elm City Hotel, an Ascend Collection Hotel
Lobby

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 star property
Brattleboro
8.8 out of 10, Excellent, (1,001 reviews)
"Room spotless, welcoming & friendly staff especially in the breakfast area"
United States
Dominick
The price is ฿4,665
฿5,132 total
includes taxes & fees
29 Mar - 30 Mar
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Pool

Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield
2.5 star property
Greenfield
8.6 out of 10, Excellent, (898 reviews)
"Good stay; great staff and nice clean rooms!"
United States
Peter
The price is ฿5,021
฿5,609 total
includes taxes & fees
5 Apr - 6 Apr
Hampton Inn & Suites Greenfield
Exterior

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, (766 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is ฿5,670
฿6,152 total
includes taxes & fees
31 Mar - 1 Apr
Fairfield Inn & Suites by Marriott Keene Downtown
Front of property

Vikings Villages Resort

Vikings Villages Resort
2.0 star property
Guilford
10.0 out of 10, Exceptional, (179 reviews)
"Great place and very clean!!"
United States
Emil
The price is ฿6,578
฿7,672 total
includes taxes & fees
9 Apr - 10 Apr
Vikings Villages Resort
Lobby

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,001 reviews)
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is ฿5,832
฿6,328 total
includes taxes & fees
31 Mar - 1 Apr
Courtyard by Marriott Keene Downtown
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (170 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is ฿4,500
฿4,883 total
includes taxes & fees
31 Mar - 1 Apr
The Carriage Barn Inn
Front of property

Black Mountain Inn

Black Mountain Inn
2.0 star property
Brattleboro
7.4 out of 10, Good, (488 reviews)
"This is a pet friendly hotel when we told the front desk there were loud dogs they immediately spoke to owners and moved our room Clean rooms and excellent. Firm mattress would def go back"
United States
Rita
The price is ฿2,927
฿3,220 total
includes taxes & fees
26 Mar - 27 Mar
Black Mountain Inn
Lunch and dinner served, American cuisine

Colonial Motel And Spa

Colonial Motel And Spa
3.0 star property
Brattleboro
6.8 out of 10, (1,000 reviews)
"It was good to have pool option after a ski day"
United States
Aysa
The price is ฿3,078
฿3,385 total
includes taxes & fees
26 Mar - 27 Mar
Colonial Motel And Spa
Breakfast area

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,005 reviews)
"Clean room, quiet, good price "
United States
Derek
The price is ฿2,309
฿2,540 total
includes taxes & fees
26 Mar - 27 Mar
The Covered Bridge Inn
Basic Room, Valley View | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Windmill Motel Restaurant

Windmill Motel Restaurant
2.0 star property
Bernardston
10.0 out of 10, Exceptional, (1 review)
"Staff was friendly and accommodating "
Canada
James
The price is ฿3,847
฿4,334 total
includes taxes & fees
1 Apr - 2 Apr
Windmill Motel Restaurant
Reception

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (762 reviews)
"I will not be back. What’s roach motel must be like for roaches. Loud, gross and just no thanks. Glad it’s iver"
United States
Joseph
The price is ฿2,304
฿2,534 total
includes taxes & fees
26 Mar - 27 Mar
Travelodge by Wyndham Brattleboro VT
Indoor pool

Hampton Inn Brattleboro

Hampton Inn Brattleboro
2.5 star property
Brattleboro
8.2 out of 10, Very good, (954 reviews)
"I wish I could have stayed longer. Very nice hotel "
United States
Rosa
The price is ฿4,224
฿4,647 total
includes taxes & fees
31 Mar - 1 Apr
Hampton Inn Brattleboro
Free daily buffet breakfast

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene
2.5 star property
Keene
8.8 out of 10, Excellent, (372 reviews)
"Nice room, pool, and breakfast! "
United States
Jennifer
The price is ฿5,485
฿5,951 total
includes taxes & fees
19 Apr - 20 Apr
Hampton Inn & Suites Keene
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (856 reviews)
"Great location, great staff really cool old building with lots of character"
Canada
David
The price is ฿4,024
฿4,426 total
includes taxes & fees
26 Mar - 27 Mar
Latchis Hotel
Room 4 | Hypo-allergenic bedding, free WiFi, bed sheets

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is ฿5,103
฿5,613 total
includes taxes & fees
29 Mar - 30 Mar
Colonel Williams 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

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

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

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
Winchester, New Hampshire in winter

Top Winchester Hotel Reviews

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2/10 Terrible
"Our room for the night was gross. The blankets had brown smears on them, the bathroom had hair and dirt everywhere, the tv wouldn't change channels, and to top it off the fire alarms battery compartment was open with absolutely no batteries in it. This place was cheaper for the area, so I didn't have high hopes for it to begin with, but it was much worse than expected. Will not recommend and will not be back. "
Christina 1-night trip
Posted 8 hours ago
Days Inn by Wyndham Keene NH

More cheap stays in Winchester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road Brattleboro VT
The price is ฿2,309 per night from 26 Mar to 27 Mar
฿2,309
฿2,540 total
26 Mar - 27 Mar
includes taxes & fees
7.6/10 Good! (1,005 reviews)

Frequently asked questions

What's the best place to stay in Winchester?
The Colonial Hotel, located 26.3 mi (42.3 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 Colonial Motel And Spa and Hampton Inn Brattleboro. 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: Features a sauna, an indoor pool and free self parking. Colonial Motel And Spa and Hampton Inn Brattleboro 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 8 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 Cass Pond, Rhododendron State Park and Royalston State Forest. A couple of additional sights to add to your itinerary are New England Sweetwater Farm & Distillery and Pisgah State Park. 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.