Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Hotels recommended for families in Winchester
8.4 out of 10, Very good, (1,007)
8.4/10
Very good
(1,007)
The price is AED 520
AED 520
AED 564 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHG2.5 star property
Brattleboro
9.0 out of 10, Wonderful, (1,004)
9.0/10
Wonderful
(1,004)
The price is AED 529
AED 529
AED 582 total
includes taxes & fees
22 Nov - 23 Nov
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel2.5 star property
Keene
8.6 out of 10, Excellent, (1,005)
8.6/10
Excellent
(1,005)
The price is AED 489
AED 489
AED 530 total
includes taxes & fees
11 Nov - 12 Nov
8.6 out of 10, Excellent, (1,001)
8.6/10
Excellent
(1,001)
The price is AED 439
AED 439
AED 483 total
includes taxes & fees
11 Nov - 12 Nov
9.2 out of 10, Wonderful, (82)
9.2/10
Wonderful
(82)
The price is AED 334
AED 334
AED 373 total
includes taxes & fees
15 Nov - 16 Nov
9.4 out of 10, Exceptional, (426)
9.4/10
Exceptional
(426)
The price is AED 440
AED 440
AED 491 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-912.5 star property
Brattleboro
8.6 out of 10, Excellent, (899)
8.6/10
Excellent
(899)
The price is AED 417
AED 417
AED 458 total
includes taxes & fees
22 Nov - 23 Nov
Fairfield Inn & Suites by Marriott Keene Downtown
Fairfield Inn & Suites by Marriott Keene Downtown3.0 star property
Keene
8.8 out of 10, Excellent, (810)
8.8/10
Excellent
(810)
The price is AED 712
AED 712
AED 772 total
includes taxes & fees
17 Nov - 18 Nov
Top Winchester Hotel Reviews
Centennial House
Centennial HouseNorthfield
10/10 Excellent
My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne
My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne
Anonymous traveler
Vikings Villages Resort
Vikings Villages ResortGuilford
10/10 Excellent
I would leave all my possessions behind to live in this cabin forever.
I would leave all my possessions behind to live in this cabin forever.
Diego
Windmill Motel Restaurant
Windmill Motel RestaurantBernardston
10/10 Excellent
Clean and comfortable. Free snacks.
Clean and comfortable. Free snacks.
David
The Inn At Crumpin Fox
The Inn At Crumpin FoxBernardston
10/10 Excellent
I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.
I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.
Anonymous traveler
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection HotelWest Chesterfield
10/10 Excellent
Everybody there was very pleasant. The entire building is immaculate. Wonderful peaceful setting on the Connecticut River.
Everybody there was very pleasant. The entire building is immaculate. Wonderful peaceful setting on the Connecticut River.
James
Inn on Putney Road
Inn on Putney RoadBrattleboro
10/10 Excellent
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Victoria
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHGBrattleboro
10/10 Excellent
A nice, clean, quiet room. Comfortable bed. Reception was very pleasant.
A nice, clean, quiet room. Comfortable bed. Reception was very pleasant.
Anthony
Hampton Inn & Suites Keene
Hampton Inn & Suites KeeneKeene
10/10 Excellent
The staff are among the kindest people I’ve ever encountered at a hotel. Simply amazing
The staff are among the kindest people I’ve ever encountered at a hotel. Simply amazing
kristin
Chesterfield Inn
Chesterfield InnWest Chesterfield
10/10 Excellent
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Beverly
Latchis Hotel
Latchis HotelBrattleboro
10/10 Excellent
Great Location! Parking is little tight, accommodations are made and you are informed on where else you can leave your car safely. Plenty of things to do within walking distance. Our room was large and well appointed, with a wonderful view. Would stay there again, in a heartbeat
Great Location! Parking is little tight, accommodations are made and you are informed on where else you can leave your car safely. Plenty of things to do within walking distance. Our room was large and well appointed, with a wonderful view. Would stay there again, in a heartbeat
Anonymous traveler
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection HotelKeene
10/10 Excellent
Friendly staff and clean, spacious room. Breakfast was very good!!
Friendly staff and clean, spacious room. Breakfast was very good!!
Kristine
The Carriage Barn Inn
The Carriage Barn InnKeene
10/10 Excellent
Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++
Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++
Richard
Best Western Plus Keene Hotel
Best Western Plus Keene HotelKeene
10/10 Excellent
Professional staff. Clean & attractive.
Some quests noisy in halls tho.
Professional staff. Clean & attractive.
Some quests noisy in halls tho.
Susan
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91Brattleboro
10/10 Excellent
The room was clean and the staff was wonderful
The room was clean and the staff was wonderful
Julianne
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene DowntownKeene
10/10 Excellent
Everything about this hotel was good. The staff, the room, and the location were all great.
Everything about this hotel was good. The staff, the room, and the location were all great.
Vic
Hampton Inn Brattleboro
Hampton Inn BrattleboroBrattleboro
10/10 Excellent
Arrived late and were greeted by 2 friendly associates at the desk. There were coffee, tea, hot cocoa, cookies, cheese and crackers available. A welcoming lobby with fireplace. Room was nice, comfortable and clean. Lots of outlets in room. Indoor pool was nice, clean, and heated. hot tub was very relaxing after days of skiing. Continental breakfast was very good and had a variety of choices. We were pleasantly surprised with our choice.
Arrived late and were greeted by 2 friendly associates at the desk. There were coffee, tea, hot cocoa, cookies, cheese and crackers available. A welcoming lobby with fireplace. Room was nice, comfortable and clean. Lots of outlets in room. Indoor pool was nice, clean, and heated. hot tub was very relaxing after days of skiing. Continental breakfast was very good and had a variety of choices. We were pleasantly surprised with our choice.
K.White
Colonel Williams Inn
Colonel Williams InnBrattleboro
10/10 Excellent
Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...
Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...
Ann
Four Columns Inn
Four Columns InnNewfane
10/10 Excellent
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
Nettie
Frequently Asked Questions
What are some of the best vacation rentals in Winchester?
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: Visitors like this Winchester vacation home rental. It is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. 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?
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 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 Birch Point, Cass Pond, and Royalston State Forest. A couple of additional sights to add to your agenda are Winchester Speedpark 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.
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 traveler data. Other good options for your stay in the area are The Colonial Hotel and Latchis Hotel. See all available top hotels, or vacation rentals in Winchester.