Title: 3 Stars Hotels in Winchester, New Hampshire from CA $179 - Find Cheap Winchester Hotels With 3 Stars | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx3000447144)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d3000447144.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000447144.Destination-Travel-Guides) ![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 3 Stars Hotels in Winchester, New Hampshire from CA $179 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winchester 3 Star Hotels Tonight [Nov 29 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-29&endDate=2025-11-30&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-30&endDate=2025-12-01&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-05&endDate=2025-12-07&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=30&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester 3 Star Hotels ![Interior](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/d25d3b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e4ae1b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/b4578f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Hotel Gardner 8.8/10 Excellent (1011) "Great hotel, fantastic restaurant, wonderful place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2557x3y3-db499e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-dbaacfef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel Keene 8.4/10 Very good (1006) "Great staff, clean room, nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DORTHY CA $194 CA $211 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/b043b966.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/8eb2a3d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9cdfa045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Keene Downtown Keene 8.8/10 Excellent (1007) "Lovely hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ronald CA $225 CA $244 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/2651a899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/c66d09dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/bffb585f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonial Motel And Spa Brattleboro 6.8/10 (1005) "Nice place to stay for the night." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin CA $168 CA $184 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/eba22fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/78a9a11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/0bc486c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blooming Inn Shelburne Falls 9.2/10 Wonderful (121) "When visiting the friends that live in Shelburne Falls; I wouldn't stay anywhere else." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) christian CA $126 CA $209 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/3e2c5f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/9e088ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/w997h675x3y2-8e010353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/231b3a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centennial House Northfield 9.6/10 Exceptional (173) "The house was cozy and inviting. Felt the history all around me and the breakfast made and served by Joan was great. We recommend this place for those looking for that historical b&b experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $260 CA $275 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/38ec3c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/fdd13f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/54ed3ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/a963d997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Engel House Jacksonville 9.2/10 Wonderful (17) "A very quaint property. The room was comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank [](https://www.expedia.ca/Jacksonville-Hotels-The-Engel-House.h67598596.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/df603ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Blue Room](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/a33464ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/ca21030b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/6c1e93ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Barn Inn Keene 9.6/10 Exceptional (165) "Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) natalia CA $178 CA $193 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/771bf86d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Courtyard View](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/c0c06736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/8c5e9bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/a95a8daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green River Bridge Inn Guilford 8.4/10 Very good (13) "Beautiful Inn and property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JaDean [](https://www.expedia.ca/Brattleboro-Hotels-Green-River-Bridge-Inn.h117293650.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Carriage House C](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/8a063a5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 9 | View from room](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/75e32be4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/7fbb1dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonel Williams Inn Brattleboro 9.8/10 Exceptional (340) "Very nice historic inn. We enjoyed our stay. Breakfast was exceptional." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) scott CA $203 CA $224 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/116000000/115210000/115205000/115204905/811c172f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/116000000/115210000/115205000/115204905/6d819f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/116000000/115210000/115205000/115204905/667dcf51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/116000000/115210000/115205000/115204905/c67c1b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Trails: Artsy Mtn-view Getaway in Vernon! Vernon 10/10 Exceptional (1) "Nice place out of the way but not too far from main roads, quiet and cozy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julian [](https://www.expedia.ca/Vernon-Hotels-Walk-To-Trails-Artsy-Mtn-View-Getaway-In-Vernon.h115204905.Hotel-Information) ![Room, Private Bathroom (Queen Guest Room)](https://images.trvl-media.com/lodging/20000000/19130000/19125800/19125741/e5beb9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/20000000/19130000/19125800/19125741/d8ac119f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (King Guest Room) | In-room dining](https://images.trvl-media.com/lodging/20000000/19130000/19125800/19125741/4a0c11cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (King Suite Guest Room) | Living area](https://images.trvl-media.com/lodging/20000000/19130000/19125800/19125741/fe0d6ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Kampfires Brattleboro 9.4/10 Exceptional (43) "The guest house and as new. It was very comfortable for the entire family and we would go back again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy E [](https://www.expedia.ca/Brattleboro-Hotels-The-Inn-At-Kampfires.h19125741.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/8e41f5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/ee713f10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/575b648c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94480000/94478900/94478890/74905170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Home w/ Modern Updates on < 4 Acres Royalston 10/10 Exceptional (2) "Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa [](https://www.expedia.ca/Royalston-Hotels-Historic-Home-W-Modern-Updates-On-35-Acres.h94478890.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/111000000/110970000/110960600/110960538/f6d20167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110970000/110960600/110960538/4c9ad137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110970000/110960600/110960538/8063eaa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110970000/110960600/110960538/b3034be1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Waterfront Gem w/ Dock on Lake Monomonac Winchendon [](https://www.expedia.ca/Winchendon-Hotels-Modern-Waterfront-Gem-W-Dock-On-Lake-Monomonac.h110960538.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/e38119ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/f8f9ccc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/fbd33027.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/106000000/105220000/105211800/105211754/ae45e84d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint Massachusetts Home w/ Yard & Grill! Gill [](https://www.expedia.ca/Gill-Hotels-Quaint-Massachusetts-Home-W-Yard-Grill.h105211754.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572765/0a084529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572765/b66861c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572765/37dcd029.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572765/c9fe6533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hike & Swim On-site: Cozy Falls Brook Cabin Brattleboro 10/10 Exceptional (2) "This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sarah [](https://www.expedia.ca/Brattleboro-Hotels-Cozy-Falls-Brook-Cabin-Hike-Swim-On-Site.h93572765.Hotel-Information) ![Cottage (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94382500/94382406/d03db9f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94382500/94382406/7aa87888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94382500/94382406/2daa3eee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94390000/94382500/94382406/93ef2670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Jaffrey Cottage w/ Deck & Grill! Jaffrey [](https://www.expedia.ca/Jaffrey-Hotels-Charming-Jaffrey-Cottage-W-Mount-Monadnock-Views.h94382406.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548200/93548124/8938a3ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548200/93548124/59f86f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548200/93548124/170d5b8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93550000/93548200/93548124/d4fa06af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilmington Home on 18 Acres ~ 9 Mi to Skiing! Wilmington 10/10 Exceptional (1) [](https://www.expedia.ca/Wilmington-Hotels-Wilmington-Home-On-18-Acres-9-Mi-To-Skiing.h93548124.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/e20cf265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/3391c48a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![28-inch flat-screen TV with satellite channels, TV, DVD player](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/9658e53a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/503a62e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cavalier Cottage B&B Shelburne Falls 9.0/10 Wonderful (2) "Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jennifer [](https://www.expedia.ca/Shelburne-Falls-Hotels-Cavalier-Cottage-BB.h18610415.Hotel-Information) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554500/98554418/0fc65f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554500/98554418/ad7b1e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554500/98554418/5dc7f21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment (1 Bedroom) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554500/98554418/d81decd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakefront Orange Vacation Rental - Pet Friendly! Orange 10/10 Exceptional (1) "Lovely, very clean, and well appointed. Host was amazing, 2 rocking chairs on front stoop overlooking the water was beautiful, peaceful.The interiorand decor was beautiful and very comfortable. We used our kayaks, which was great. It is an in̈cline downhill to carry your kayak. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jean [](https://www.expedia.ca/Orange-Hotels-Lakefront-Orange-Vacation-Rental-Pet-Friendly.h98554418.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F3Star-Winchester-Hotels.s30-0-d3000447144.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F3Star-Winchester-Hotels.s30-0-d3000447144.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 3-star hotels. See all 4-star hotels in Winchester. ![Four Columns Inn](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Four Columns Inn 21 West Street Newfane VT CA $164 CA $179 total Dec 15 - Dec 16 includes taxes & fees 9.6/10 Exceptional! (12 reviews) [](https://expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) ![Inn on Putney Road](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Inn on Putney Road 192 Putney Road Brattleboro VT CA $373 CA $410 total Dec 1 - Dec 2 includes taxes & fees 9.8/10 Exceptional! (56 reviews) [](https://expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) ![Chesterfield Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/a23bd7ee_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Chesterfield Inn 20 Cross Roadd West West Chesterfield NH CA $421 CA $457 total Dec 1 - Dec 2 includes taxes & fees 9.6/10 Exceptional! (30 reviews) [](https://expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F11%2F2025&endDate=01%2F12%2F2025®ionId=3000447144&star=30) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F11%2F2025&endDate=01%2F12%2F2025®ionId=3000447144&star=30&star=30&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F11%2F2025&endDate=01%2F12%2F2025®ionId=3000447144&star=30&star=30&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F11%2F2025&endDate=01%2F12%2F2025®ionId=3000447144&star=30&star=30&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F11%2F2025&endDate=01%2F12%2F2025®ionId=3000447144&star=30&star=30&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F11%2F2025&endDate=01%2F12%2F2025®ionId=3000447144&star=30&star=30&amenities=WATER_PARK) 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. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2025-12-13&endDate=2025-12-14&adults=2®ionId=3000447144) ![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=900&h=591&p=1&q=high) ## Top Winchester Hotel Reviews ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "Staff was very polite, the restaurant was lovely the service was amazing the room was comfortable and relaxing we loved it :)" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "Staff was accommodating. Got a Free upgrade to my room" [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Courtyard by Marriott Keene Downtown](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f_y.jpg) ### Courtyard by Marriott Keene Downtown 10/10 Excellent "Clean; great breakfast; quiet" [](https://expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "YES, the room was SPOTLESS!!! An indoor Pool, Sauna & Continental Breakfast made this stay a PLUS!!! (Waffles, Toast, Coffee, Bagels, Cereal & Fresh Fruit). A definite choice for another visit!!!" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ## Find out more about Winchester The top 3 Stars hotels in Winchester, Winchester may offer some of the best discounts and rates, but these properties are anything but average. Travelers love Winchester 3 Stars hotels for their top quality services, just-like-home amenities, and wallet-friendly prices. You can even get access to fantastic perks like delectable restaurants, so-cool cocktail bars, and spacious fitness centres. Use the travel tools at Expedia.ca to find a cheap deal on a 3 Stars upscale hotel in Winchester for a first-class experience, or book an inexpensive rate on one of the cheap 3 Stars hotels in Winchester neighbourhoods near the city’s best attractions. We’ll even help you find vacation packages to go with your three star hotel in Winchester. From last-minute work trips to long-awaited family getaways, we offer all the essentials you need to enjoy your jaunt through Winchester. ## Frequently asked questions ### How much does it cost to stay in a 3-star hotel in Winchester? > To find a reasonably priced 3-star hotel in Winchester, use our handy filter tools. Decide on your budget, select your amenities and loads more. Additionally, you can sort your search results so the most affordable options appear first. > > > > - Search for the lowest price per night right now from CA $179 ### What is the difference between a 4-star and 3-star hotel in Winchester? > The most obvious difference between a 3- and 4-star hotel in Winchester will be the quality of service and availability of creature comforts. 3-star hotels are usually lower priced and offer the amenities and services required for your comfort, such as WiFi, breakfast and a gym. You can expect a bit more at a 4-star hotel — think upscale interiors, premium bathroom products and extra touches like spa centres. ### What is the difference between a 3-star hotel and a motel in Winchester? > Among the perks of staying at a motel in or close to Winchester is inexpensive rates. This means more cash in your wallet to discover some top attractions. Often positioned near highways and airports, and with ample parking, this style of getaway is a favourite among road trippers. When you stay at a 3-star hotel, you'll get more than just comfy accommodations to kick back in. 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