Find vacation rentals that suit your style
Our top choices for Winchester cottages
1. Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Cabin & Sauna on Lake Monomonac near Mt. MonadnockRindge
10.0 out of 10, Exceptional, (14 reviews)
10/10
Exceptional
(14 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
clifford t.
$242 nightly
The price is $263
$263 total
Nov 15 - Nov 16
Total with taxes and fees
2. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
2 Bed 1.5 Bath on Pool Pond Close Franklin PierceRindge
10.0 out of 10, Exceptional, (25 reviews)
10/10
Exceptional
(25 reviews)
"Excellent property, really enjoyed this beautiful home."
"Excellent property, really enjoyed this beautiful home."Susan G.
$345 nightly
The price is $374
$374 total
Nov 15 - Nov 16
Total with taxes and fees
3. Cozy Tiny House on Main Street. Fully Renovated.
Cozy Tiny House on Main Street. Fully Renovated.Dublin
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"David W.
$272 nightly
The price is $291
$291 total
Nov 13 - Nov 14
Total with taxes and fees
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.
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.
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.
Top reviews in Winchester
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
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
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
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
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
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
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
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
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
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
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
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
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
Deerfield Inn
Deerfield InnDeerfield
10/10 Excellent
Excellent stay!
Excellent stay!
Debbie
Shelburne Springs Hotel
Shelburne Springs HotelShelburne Falls
10/10 Excellent
We travelled for one night and it’s a gem. Spacious, easy in and out. Very comfortable.
We travelled for one night and it’s a gem. Spacious, easy in and out. Very comfortable.
Brian
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
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