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Winchester Hotels

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Top 10 trending Winchester hotels

Our top choices for Winchester hotels

The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1008)
"Very convenient and clean hotel with well appointed rooms, easy and plentiful parking. "
The Colonial Hotel
The Inn At Crumpin Fox
Front of property

The Inn At Crumpin Fox

2.5 star property
9.2 out of 10, Wonderful, (323)
"It was a peaceful, clean, quiet stay. "
The price is P9,960
P11,126 total
includes taxes & fees
Sep 21 - Sep 22
The Inn At Crumpin Fox
The Covered Bridge Inn
Exterior detail

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1003)
"Good value for a two night stay for work "
The price is P5,010
P5,510 total
includes taxes & fees
Sep 21 - Sep 22
The Covered Bridge Inn
Black Mountain Inn
Front of property

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (464)
"Friendly staff. Room was nice "
The price is P7,781
P8,559 total
includes taxes & fees
Sep 21 - Sep 22
Black Mountain Inn
Best Western Plus Keene Hotel
Premium bedding, individually decorated, individually furnished, desk

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very Good, (1003)
"Great for stay"
The price is P7,911
P8,584 total
includes taxes & fees
Sep 21 - Sep 22
Best Western Plus Keene Hotel
Riverside Hotel, an Ascend Collection Hotel
Sundeck

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (597)
"Great place!"
The price is P9,143
P9,921 total
includes taxes & fees
Sep 22 - Sep 23
Riverside Hotel, an Ascend Collection Hotel
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free daily on-the-go breakfast

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1002)
"Good room, great breakfast options "
The price is P10,188
P11,207 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (704)
"I was only there for a few hours sleep "
The price is P4,558
P5,014 total
includes taxes & fees
Sep 21 - Sep 22
Travelodge by Wyndham Brattleboro VT
Gardner Inn
Exterior

Gardner Inn

2.0 star property
5.0 out of 10, (8)
"The property needs work but hte staff was pleasant and the facility was quiet. "
The price is P5,635
P6,632 total
includes taxes & fees
Sep 21 - Sep 22
Gardner Inn
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Breakfast area

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
9.4 out of 10, Exceptional, (423)
"Great price, close to town and really nice staff"
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (687)
"This was a nice stay, thanks"
The price is P8,298
P9,128 total
includes taxes & fees
Sep 22 - Sep 23
Comfort Inn & Suites Brattleboro I-91
Latchis Hotel
Hiking

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (789)
"Great stay!"
The price is P8,196
P9,015 total
includes taxes & fees
Sep 21 - Sep 22
Latchis Hotel
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1004)
"Always a pleasure to stay at the Colonial"
The price is P7,968
P8,765 total
includes taxes & fees
Sep 21 - Sep 22
Colonial Motel And Spa
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.0 out of 10, Good, (1004)
"Would stay again"
The price is P6,096
P6,614 total
includes taxes & fees
Sep 21 - Sep 22
Days Inn by Wyndham Keene NH
Hampton Inn Brattleboro
Free breakfast

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very Good, (884)
"It was close by to our event and very hospitable!"
The price is P7,735
P8,508 total
includes taxes & fees
Sep 29 - Sep 30
Hampton Inn Brattleboro
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1004)
"Very enjoyable stay"
The Putney Inn
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (738)
"We stayed in the loft room and it was great! Right downtown, free parking right out the back and the staff is super nice. I would definitely go back!"
The price is P10,415
P11,301 total
includes taxes & fees
Oct 5 - Oct 6
Fairfield Inn & Suites by Marriott Keene Downtown
Keene Elm City Hotel, an Ascend Collection Hotel
Indoor pool

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 star property
8.4 out of 10, Very Good, (898)
"Clean room - friendly staff - convenient location "
The price is P6,608
P7,170 total
includes taxes & fees
Sep 24 - Sep 25
Keene Elm City Hotel, an Ascend Collection Hotel
Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (111)
"Lovely Inn and very responsive and approachable staff. "
The price is P5,122
P8,511 total
includes taxes & fees
Oct 5 - Oct 6
Blooming Inn
Hampton Inn & Suites Greenfield
Down comforters, desk, blackout drapes, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (847)
"The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. "
The price is P9,676
P10,808 total
includes taxes & fees
Sep 29 - Sep 30
Hampton Inn & Suites Greenfield
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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Learn more about Winchester

Get away to relaxing Winchester! Enjoy the lake views, forests, and more.

See all hotels in Winchester
Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

The Colonial Hotel

The Colonial Hotel

10/10 Excellent
"Very convenient location. Facility is clean and attractive. Very comfortable. "
Jane 1-night trip
Posted 2 days ago
The Colonial Hotel

More cheap stays in Winchester

More cheap stays in Winchester

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd, Keene, NH
The price is P6,608 per night from Sep 24 to Sep 25
P6,608
P7,170 total
Sep 24 - Sep 25
includes taxes & fees
8.4/10 Very Good! (898 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 traveler data. Other good options for your stay in the area are Hampton Inn Brattleboro and Keene Elm City Hotel, an Ascend Collection 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, 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: Features a sauna, an indoor pool, and free self parking. Hampton Inn Brattleboro and Keene Elm City Hotel, an Ascend Collection 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 Rhododendron State Park, Ashuelot River, and Cass Pond. A couple of additional sights to add to your agenda are Pisgah State Park 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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