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Winchester Hotels from S$114

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12 Oct - 13 Oct
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13 Oct - 14 Oct
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17 Oct - 19 Oct
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24 Oct - 26 Oct

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Top 10 trending Winchester hotels

The Colonial Hotel
Interior

The Colonial Hotel

3.0 star property
8.8 out of 10, Excellent, (1010)
"Nice place"
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, (325)
"Staff very accomodating, very nice room, "
The price is S$189
includes taxes & fees
2 Nov - 3 Nov
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, (1013)
"Good value for a two night stay for work "
The price is S$136
includes taxes & fees
13 Oct - 14 Oct
The Covered Bridge 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, (1014)
"Hotel was great."
The price is S$217
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Keene Hotel
Black Mountain Inn
Front of property

Black Mountain Inn

2.0 star property
7.4 out of 10, Good, (467)
"Staff is extremely friendly & helpful."
The price is S$161
includes taxes & fees
2 Nov - 3 Nov
Black Mountain Inn
Riverside Hotel, an Ascend Collection Hotel
Sun deck

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (610)
"Loved my stay"
The price is S$214
includes taxes & fees
27 Oct - 28 Oct
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, (1000)
"Good room, great breakfast options "
The price is S$221
includes taxes & fees
10 Nov - 11 Nov
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, (717)
"For the money during peep season it was ok. Otherwise it’s a low quality stay"
The price is S$114
includes taxes & fees
19 Oct - 20 Oct
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 S$148
includes taxes & fees
2 Nov - 3 Nov
Gardner Inn
Days Inn by Wyndham Keene NH
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Keene NH

2.0 star property
7.0 out of 10, Good, (1008)
"Comfortable night stay. Would repeat "
The price is S$147
includes taxes & fees
11 Nov - 12 Nov
Days Inn by Wyndham Keene NH
Comfort Inn & Suites Brattleboro I-91
Lobby

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (705)
"Absolutely perfect stay for a business trip"
The price is S$179
includes taxes & fees
2 Nov - 3 Nov
Comfort Inn & Suites Brattleboro I-91
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1002)
"Nice place to stay for the night."
The price is S$200
includes taxes & fees
13 Oct - 14 Oct
Colonial Motel And Spa
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, (428)
"Great price, close to town and really nice staff"
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Latchis Hotel
Hiking

Latchis Hotel

2.5 star property
8.4 out of 10, Very good, (801)
"Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. "
The price is S$187
includes taxes & fees
4 Nov - 5 Nov
Latchis Hotel
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, (919)
"Nice place to stay "
The price is S$176
includes taxes & fees
26 Oct - 27 Oct
Keene Elm City Hotel, an Ascend Collection Hotel
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, (741)
"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 S$231
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Keene Downtown
The Putney Inn
Exterior

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1006)
"Very enjoyable stay"
The Putney Inn
Hampton Inn Brattleboro
Free breakfast

Hampton Inn Brattleboro

2.5 star property
8.2 out of 10, Very good, (903)
"Breakfast area was the best I've seen in a while!"
The price is S$141
includes taxes & fees
5 Nov - 6 Nov
Hampton Inn Brattleboro
Hampton Inn & Suites Greenfield
Down duvets, desk, blackout curtains, soundproofing

Hampton Inn & Suites Greenfield

2.5 star property
8.6 out of 10, Excellent, (861)
"The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. "
The price is S$225
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Greenfield
Hampton Inn & Suites Keene
Reception

Hampton Inn & Suites Keene

2.5 star property
8.8 out of 10, Excellent, (335)
"Great hotel with friendly staff"
The price is S$238
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Keene
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

New England Sweetwater Farm & Distillery

You can take time to visit New England Sweetwater Farm & Distillery during your travels to Winchester. While you're in the area, stroll along the lakeside.
See properties

Richmond Wildlife Manangement Area

Explore the great outdoors at Richmond Wildlife Manangement Area, a lovely green space in Richmond.
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
Photo by Donny Campos
Open Photo by Donny Campos

Top Winchester Hotel Reviews

Vikings Villages Resort

Vikings Villages Resort

10/10 Excellent
"Cabin was cozy, clean and comfortable. Perfect size for kitchen. Loved, loved the towels - they smelled so good"
DAWN 1-night trip
Posted 2 days ago
Vikings Villages Resort

More cheap stays in Winchester

Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road, Brattleboro, VT
The price is S$141 per night from 5 Nov to 6 Nov
S$141
5 Nov - 6 Nov
includes taxes & fees
8.2/10 Very Good! (901 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 Econo Lodge 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, 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. Econo Lodge Brattleboro and Keene Elm City Hotel, an Ascend Collection 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 Rhododendron State Park, Ashuelot River and Cass Pond. A couple of additional sights to add to your itinerary are Pisgah State Park 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 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.

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