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 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-22&endDate=2025-10-23&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-23&endDate=2025-10-24&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This 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) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester 2 Star Hotels ![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) ![Property entrance](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/548b84a8.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) ### The Covered Bridge Inn Brattleboro 7.6/10 Good (1000) "Good value for a two night stay for work " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jim CA $132 CA $145 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.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/1000000/20000/14500/14439/211acecc.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 (932) "Nice place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $175 CA $190 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/dd202f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (713) "Absolutely perfect stay for a business trip" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyndsey CA $176 CA $194 total includes taxes & fees Nov 9 - Nov 10 [](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) ![View from property](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/2e9ea916.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/501b3c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Latchis Hotel Brattleboro 8.4/10 Very good (806) "Is a great historic building with great charm. Hope to stay there again soon." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roger CA $184 CA $203 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/fa5ce310.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) ![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) "Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judy CA $142 CA $154 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/279e51da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/1ad12332.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) ### Econo Lodge Brattleboro Brattleboro 5.4/10 (583) "Most disgusting place I've ever seen to" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $95 CA $105 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.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/3000000/2880000/2877400/2877372/1836db06.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) ![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) ### Riverside Hotel, an Ascend Collection Hotel West Chesterfield 9.6/10 Exceptional (617) "Loved my stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $213 CA $231 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) ![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/d56bdb03.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/486cbce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Greenfield Greenfield 8.6/10 Excellent (867) "The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $177 CA $197 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/3973f8d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c.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) ### The Putney Inn Putney 8.4/10 Very good (1000) "Reasonable price for an overnight stay. Ample parking, very quiet and easy access to I 91." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MICHAEL CA $107 CA $118 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/1eab968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/f3cee559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro Brattleboro 8.2/10 Very good (907) "Breakfast area was the best I've seen in a while!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $134 CA $147 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.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) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/2c765229.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) ### Travelodge by Wyndham Brattleboro VT Brattleboro 6.0/10 (726) "Reasonable rate for the the accomadations." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $112 CA $124 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/d0dd0859.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) ### Hampton Inn & Suites Keene Keene 8.8/10 Excellent (340) "Great hotel with friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $219 CA $238 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.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) ![Banquet hall](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/232c3c13.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) ![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 (331) "Staff very accomodating, very nice room, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $183 CA $204 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/e51d292e.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) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG Brattleboro 8.8/10 Excellent (1002) "Good room, great breakfast options " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan CA $209 CA $230 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.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) ![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) ![Flat-screen TV, iPod dock](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/273d8c13.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Felicia CA $237 CA $257 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/b26bd55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverhouse by Weekender (Formerly Jack Daniels Inn) Peterborough 9.4/10 Exceptional (430) "Super cute place! Would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle CA $169 CA $199 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.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) ![Single Room](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/f55aec94.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) ![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d66e17b0.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lou CA $139 CA $155 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.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) ![Exterior](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/5b51cbf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Chalet](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6b906caa.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) ### Vikings Villages Resort Guilford 10/10 Exceptional (146) "Favorite place to stay in New England bar none!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $285 CA $332 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/1bf7bbfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Mountain Inn Brattleboro 7.4/10 Good (470) "Staff is extremely friendly & helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Theresa CA $158 CA $173 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/73000000/72620000/72611300/72611296/3cda440a.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) ![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) ![Staircase](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/d7fa40cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Burrell House Keene 9.6/10 Exceptional (152) "Very helpful, kind staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paitris CA $172 CA $192 total includes taxes & fees Oct 27 - Oct 28 [](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 $200 CA $224 total Oct 26 - Oct 27 includes taxes & fees 8.8/10 Excellent! (1,014 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 $210 CA $228 total Oct 26 - Oct 27 includes taxes & fees 8.2/10 Very Good! (1,023 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 $196 CA $216 total Oct 23 - Oct 24 includes taxes & fees 6.6/10 (1,008 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=23%2F10%2F2025&endDate=24%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=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000447144&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%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=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000447144&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000447144&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%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=2025-11-05&endDate=2025-11-06&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 ![Black Mountain Inn](//images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c_y.jpg) ### Black Mountain Inn 10/10 Excellent "Nice for one night" [](https://expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "Viking Villages is incredible. Location is beautiful and they have hit every little thing to add to ambiance. Lodging is cozy and has everything you need for a little getaway. We will be back, highly recommend. " [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Gardner Inn](//images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d13ce465_y.jpg) ### Gardner Inn 8/10 Good "Clean room " [](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 6/10 Okay "The staff was nice and helpful. We checked in ok. I was told the room was ready, but it wasn't. Tv didn't work right, needed help getting the fridge running, had to ask for more towels because we only had a hand towel in the room, the mattress was a 2 out 5 at best and finally, had to give them the pizza boxes from the closet. " [](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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