Title: 2 Stars Hotels in Winchester, New Hampshire from CA $105 - Find Cheap Winchester Hotels With 2 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) ![](https://mediaim.expedia.com/destination/2/ea42c861000f38e6206ed251ac7da597.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Donny Campos # 2 Stars Hotels in Winchester, New Hampshire from CA $105 ![](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 2 Star Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-15&endDate=2025-10-16&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester 2 Star Hotels ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/1eab968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/b79a8982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro Brattleboro 8.2/10 Very good (904) "Breakfast area was the best I've seen in a while!" CA $140 CA $154 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/95e5b046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/5e6bf716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/f8a38dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Elm City Hotel, an Ascend Collection Hotel Keene 8.4/10 Very good (925) "Nice place to stay " CA $176 CA $191 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/acbfdae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/c5f36674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/548b84a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Covered Bridge Inn Brattleboro 7.8/10 Good (1018) "Good value for a two night stay for work " CA $156 CA $171 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/907a3236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/89435dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/3973f8d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Putney Inn Putney 8.4/10 Very good (1006) "Friendly staff at check in. Plenty of parking. Convenient location to break up a long trip." CA $106 CA $117 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/9e4b70fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/fa5ce310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/b4de2547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Keene NH Keene 7.0/10 Good (1011) "Comfortable night stay. Would repeat " CA $148 CA $161 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/dd202f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/9ca0f525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/32bcc2b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (709) "Absolutely perfect stay for a business trip" CA $176 CA $194 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Hiking](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Accessible, Ensuite (Old Solarium Queen)](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/0d6df977.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/501b3c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Latchis Hotel Brattleboro 8.4/10 Very good (802) "Very nice vintage hotel" CA $182 CA $201 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/19b6c01d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/1e752373.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/f50c0b34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/17df5014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Brattleboro VT Brattleboro 6.0/10 (723) "For the money during peep season it was ok. Otherwise it’s a low quality stay" CA $112 CA $124 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/601d670f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/fab2ddfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/e38be73f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Hotel, an Ascend Collection Hotel West Chesterfield 9.6/10 Exceptional (611) "Loved my stay" CA $214 CA $232 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/486cbce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/a441dd28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/42933ea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Greenfield Greenfield 8.6/10 Excellent (863) "The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. " CA $218 CA $243 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/a961b35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/7abf75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/bbdb2e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Keene Keene 8.8/10 Excellent (335) "Great hotel with friendly staff" CA $238 CA $258 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/178059c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/12c65397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/26331746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/279e51da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Brattleboro Brattleboro 5.4/10 (579) "Most disgusting place I've ever seen to" CA $95 CA $105 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/a258302a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/abfe038f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/6ab0952d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Keene Downtown Keene 8.8/10 Excellent (742) "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!" CA $230 CA $250 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/e940457b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/232c3c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/9fd6251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn At Crumpin Fox Bernardston 9.2/10 Wonderful (326) "Staff very accomodating, very nice room, " CA $183 CA $205 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/5d62062a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/b26bd55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/93d41afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/a8d76203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverhouse by Weekender (Formerly Jack Daniels Inn) Peterborough 9.4/10 Exceptional (429) "Great price, close to town and really nice staff" CA $181 CA $211 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/2f9ec6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/465cf783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/8c8403c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Mountain Inn Brattleboro 7.4/10 Good (469) "Staff is extremely friendly & helpful." CA $158 CA $174 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d13ce465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d66e17b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/4a8be764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gardner Inn Gardner 5.4/10 (9) "The property needs work but hte staff was pleasant and the facility was quiet. " CA $136 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/707e42f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/2744f7ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/2680e185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG Brattleboro 8.8/10 Excellent (1001) "Good room, great breakfast options " CA $218 CA $240 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Deluxe Chalet](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Chalet](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/4e518b58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/5b51cbf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/w4064h2713x0y0-ac6092f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vikings Villages Resort Guilford 10/10 Exceptional (141) "Favorite place to stay in New England bar none!! " CA $285 CA $332 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/3cda440a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Queen Bed](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/5e1ddcf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Queen Bed](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/c06df8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/99e3bb30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Burrell House Keene 9.6/10 Exceptional (150) "Very helpful, kind staff" CA $186 CA $208 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.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%2F2Star-Winchester-Hotels.s20-0-d3000447144.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Winchester-Hotels.s20-0-d3000447144.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Winchester. ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Colonial Hotel 625 Betty Spring Road, Gardner, MA CA $192 CA $215 total Oct 27 - Oct 28 includes taxes & fees 8.8/10 Excellent! (1,010 reviews) [](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?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Plus Keene Hotel 401 Winchester St, Keene, NH CA $209 CA $227 total Oct 16 - Oct 17 includes taxes & fees 8.2/10 Very Good! (1,014 reviews) [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Colonial Motel And Spa 889 Putney Rd, Brattleboro, VT CA $197 CA $216 total Oct 15 - Oct 16 includes taxes & fees 6.6/10 (1,002 reviews) [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.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=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=3000447144&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=3000447144&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=3000447144&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=3000447144&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=3000447144&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=3000447144&star=20&star=20&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=2025-10-28&endDate=2025-10-29&adults=2®ionId=3000447144) ![](https://mediaim.expedia.com/destination/2/ea42c861000f38e6206ed251ac7da597.jpg?impolicy=fcrop&w=899&h=599&p=1&q=high) Photo by Donny Campos ## Top Winchester Hotel Reviews ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "From the lovely staff who maintain the property to the clean, modern and well thought out theme, the entire property was wonderful. Well designed, a beautiful nod to Nordic culture, and full of surprises like wild goats and fire pits. " [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Black Mountain Inn](//images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c_y.jpg) ### Black Mountain Inn 10/10 Excellent "Staff is extremely friendly & helpful." [](https://expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Gardner Inn](//images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d13ce465_y.jpg) ### Gardner Inn 8/10 Good "The property needs work but hte staff was pleasant and the facility was quiet. " [](https://expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) ![Econo Lodge Brattleboro](//images.trvl-media.com/lodging/1000000/860000/859400/859304/178059c7_y.jpg) ### Econo Lodge Brattleboro 10/10 Excellent "Nothing bad about inside the room (108) -- but it was next to the hallway to the stairs to the second floor, so heard occasional foot-stomps during the evening. No other noises, though. Spatious double sinks, very unusual. Huge, firm bed. The manager has quite the beautiful flowers and vegetables garden as landscaping, including some exotic trees. Obviously this will vary by season, but Coreopsis verticillata (yellow/orange/red) was in full glory, with Cosmos coming on, among other things. Also look for curry-leaf tree (Murraya koenigii)." [](https://expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.Hotel-Information) ## Find out more about Winchester Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Winchester, Winchester you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions. Several of the best hotels with 2 Stars in Winchester are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. 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