Title: 10 Historic Hotels in Windham County for 2026 | Expedia.ca [Windham County Hotels](https://expedia.ca/Destinations-In-Windham-County.d6057353.Hotel-Destinations)[Vacation Rentals in Windham County](https://expedia.ca/Destinations-In-Windham-County.d6057353.Vacation-Rental-Destinations)[Windham County Car Rentals](https://expedia.ca/Destinations-In-Windham-County.d6057353.Car-Rental-Destinations)[Windham County Vacations](https://expedia.ca/Windham-County.d6057353.Destination-Travel-Guides) ![New England is known for their covered bridges. A beautiful example is the West Dummerston Bridge over the West River in southern Vermont. #InStone](https://images.trvl-media.com/place/6057353/bdb3e72e-fca5-4208-a6a4-c09318f6a7f8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Bruce Altobelli ![](https://images.trvl-media.com/place/6057353/bdb3e72e-fca5-4208-a6a4-c09318f6a7f8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 ## Top Cities in Windham County ![](https://mediaim.expedia.com/destination/2/7293bdf66975e2ab77f3169d08030312.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brattleboro [](https://expedia.ca/Brattleboro-Hotels-Historic-Hotel.0-0-d9636-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Mount Snow featuring mountain biking as well as an individual male](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/147000/147668-Mount-Snow.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### West Dover [](https://expedia.ca/West-Dover-Hotels-Historic-Hotel.0-0-d10459-tHistoricHotel.Travel-Guide-Filter-Hotels) ![Wilmington which includes a city and autumn leaves](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93855-Southern-Vermont.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Wilmington [](https://expedia.ca/Wilmington-Hotels-Historic-Hotel.0-0-d175314-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/5dd0ae771d7a48c28ba58644a2879927.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Londonderry [](https://expedia.ca/Londonderry-Hotels-Historic-Hotel.0-0-d127228-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/ca7b3ef3eca67e517d919813ea0accfb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Bellows Falls [](https://expedia.ca/Bellows-Falls-Hotels-Historic-Hotel.0-0-d6842-tHistoricHotel.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/00a7e4f9963cb953b7bd55237cbf6671.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Grafton [](https://expedia.ca/Grafton-Hotels-Historic-Hotel.0-0-d184049-tHistoricHotel.Travel-Guide-Filter-Hotels) ## Check availability on Windham County Historic Hotels Tonight [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-13&endDate=2026-01-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-14&endDate=2026-01-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windham County historic hotels ![Porch](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/dfd331b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/4aef8677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/11b23fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/c9e22020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wilmington Inn [](https://www.expedia.ca/Wilmington-Hotels-The-Wilmington-Inn.h3532068.Hotel-Information) Wilmington 10/10 Exceptional (197 reviews) "Relaxing stay with great hiking nearby" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlotte CA $299 CA $339 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Wilmington-Hotels-The-Wilmington-Inn.h3532068.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/1c89b45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/c62129ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, dinner served, local cuisine](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/7ccafcc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tavern Room, 1 Queen Bed](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/a836019e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grafton Inn [](https://www.expedia.ca/Grafton-Hotels-Grafton-Inn.h1381178.Hotel-Information) Grafton 9.6/10 Exceptional (80 reviews) "Wonderful in every way." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.ca/Grafton-Hotels-Grafton-Inn.h1381178.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/5baffb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/452e126e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/59f5ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on Putney Road [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) Brattleboro 9.8/10 Exceptional (56 reviews) "wonderful atmosphere, great breakfast, friedly staff, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt CA $326 CA $358 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Theatre show](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/afa5570f.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) ![Hiking](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Latchis Hotel [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) Brattleboro 8.4/10 Very good (843 reviews) "Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaime CA $181 CA $199 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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) ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/81dd974d.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) ![View from room](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/4bee0dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonel Williams Inn [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) Brattleboro 9.8/10 Exceptional (342 reviews) "Absolutely stunning bed and breakfast! The room and facilities were clean and welcoming. We really enjoyed the decorations and details of the house. The breakfast was delicious! Will definitely be coming back next time we are in town for ski! Highly recommended staying at Colonel Williams! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ekaterina CA $204 CA $225 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.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/2000000/1080000/1070800/1070729/05f7e3bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/f7fdc9d8.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) ### Colonial Motel And Spa [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) Brattleboro 6.8/10 (1,003 reviews) "Great location and service " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $194 CA $214 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/b82005ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/fecb1c08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/be5c7e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/fca3b093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Nutmeg [](https://www.expedia.ca/Wilmington-Hotels-The-Nutmeg.h1482719.Hotel-Information) Wilmington 9.4/10 Exceptional (416 reviews) "very accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jarrod CA $234 CA $258 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Wilmington-Hotels-The-Nutmeg.h1482719.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/51593618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/eaa2ed2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/d926bdd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/4a49f58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Conference Center Brattleboro North [](https://www.expedia.ca/Brattleboro-Hotels-Quality-Inn-Conference-Center.h43049.Hotel-Information) Brattleboro 6.2/10 (878 reviews) "Due to precautions concerning COVID19, most of the amenities were closed. Still it is a nice, convenient property and I would definitely stay again when in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Brattleboro-Hotels-Quality-Inn-Conference-Center.h43049.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.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) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/f5b14dc0.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 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) Brattleboro 8.2/10 Very good (935 reviews) "Good breakfast, great staff and very good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valdeci CA $204 CA $224 total includes taxes & fees Jan 22 - Jan 23 [](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) ![Blackout drapes, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/7f0e9a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/cae4ce59.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 [](https://www.expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) Brattleboro 6.0/10 (740 reviews) "Great person at front desk. Motel was nicer than expected and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giovanni CA $99 CA $109 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-27&endDate=2026-01-28®ionId=6057353&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ![](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%2FDestinations-In-Windham-County-Historic-Hotel.0-0-d6057353-tHistoricHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windham-County-Historic-Hotel.0-0-d6057353-tHistoricHotel.Hotel-Filter-Destinations) ## Top Windham County Hotel Reviews ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Fantastic experience! Great staff! Very comfortable room. Thanks . " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Deerfield Valley Inn](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368_y.jpg) ### Deerfield Valley Inn 10/10 Excellent "Oz, Deerfield's host and owner, is simply 'ozsome.' Simply put. Feels like a second home away from home. Classic Vermont. Romantic fireplaces. And a very welcoming and friendly no-nonsense vibe throughout. Great value and convenience realized whenever in the Dover and Mt. Snow environs. Highly recommend this classic inn. " [](https://expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Every thing was excellent " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Inn At Mount Snow](https://images.trvl-media.com/lodging/110000000/109060000/109054300/109054249/2a223f80_y.jpg) ### Inn At Mount Snow 10/10 Excellent "Remodeled. Clean. Pool table. " [](https://expedia.ca/West-Dover-Hotels-Inn-At-Mount-Snow.h109054249.Hotel-Information) ![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg) ### Chalet 239 10/10 Excellent "Great stay " [](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information) ![Four Columns Inn](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d_y.jpg) ### Four Columns Inn 10/10 Excellent "Beautiful room and property. " [](https://expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "Great staff" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Comfy room!" [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Mount Snow Grand Summit Resort](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Ski slopes were accessible and pool was really nice. " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Jamaica ](https://www.expedia.ca/3Star-Jamaica-Hotels.s30-0-d184052.Travel-Guide-Filter-Hotels) - [Hotels near Brattleboro Common ](https://www.expedia.ca/Brattleboro-Common-Hotels.0-l553248621561865132-0.Travel-Guide-Filter-Hotels) - [Brattleboro Hotels ](https://www.expedia.ca/Brattleboro-Hotels.d9636.Travel-Guide-Hotels) - [B&B in Brookline ](https://www.expedia.ca/Brookline-Bed-And-Breakfast.d3000459594-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Brookline ](https://www.expedia.ca/Brookline-Chalets.d3000459594-aaChalets.Travel-Guide-Accommodation) - [Hotels with a Pool in Brookline ](https://www.expedia.ca/Brookline-Hotels-Hotel-With-Pool.0-0-d3000459594-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Brookline ](https://www.expedia.ca/Brookline-Hotels-Luxury-Hotel.0-0-d3000459594-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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