Title: Windham County Cottages | 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)[Things to do in Windham County](https://expedia.ca/Things-To-Do-In-Windham-County.d6057353.Travel-Guide-Activities)[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 ## Check prices for these dates In two weeks [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Windham County ![Autumn at Jones Pond - Carrabassett Valley - Maine - Bigelow Preserve Peak](https://images.trvl-media.com/place/163002/2c2fe06f-9c24-49c7-abde-ddaf8f23f7c4.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton-Cottages.d163002-aaCottages.Travel-Guide-Accommodation) ![Drone view from above a West Dover Vermont neighborhood in winter](https://images.trvl-media.com/place/10459/36c3716b-92fb-40b7-8bcf-545492fddfe3.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### West Dover [](https://expedia.ca/West-Dover-Cottages.d10459-aaCottages.Travel-Guide-Accommodation) ![Autumn colors along Connecticut River, Brattleboro, Vermont](https://images.trvl-media.com/place/9636/028a402e-1933-4649-ba79-261aea048ad3.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brattleboro [](https://expedia.ca/Brattleboro-Cottages.d9636-aaCottages.Travel-Guide-Accommodation) ![Wilmington which includes a city and autumn leaves](https://images.trvl-media.com/place/175314/9c0f0e5d-2a7c-4c89-8d88-0d1abb3d7c9a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Wilmington [](https://expedia.ca/Wilmington-Cottages.d175314-aaCottages.Travel-Guide-Accommodation) ![White winter wonderland scenery in South Londonderry, Vermont with snow covered trees, bench, pond and blue cloudy sky in the background. Cold snowy day.](https://images.trvl-media.com/place/127228/def91bc0-833e-4f3b-aaad-ceb4dc0bf45d.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Londonderry [](https://expedia.ca/Londonderry-Cottages.d127228-aaCottages.Travel-Guide-Accommodation) ![HGY9XC View of the Ball Mountain Reservoir from the top of the Ball Mountain Dam on the West River in Jamaica Vermont USA](https://images.trvl-media.com/place/184052/aaff0c92-5112-4914-98bd-67915c0912e0.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Jamaica [](https://expedia.ca/Jamaica-Cottages.d184052-aaCottages.Travel-Guide-Accommodation) ## Our top choices for Windham County cottages ![Exterior](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076053/698550fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076053/9fe7ea33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076053/505fc249.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/92000000/91080000/91076100/91076053/b7cce051.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Cottage-In-The-Woods-With-A-Firepit.h91076053.Hotel-Information) 8.6/10 Excellent (66 reviews) "A beautiful, cozy home. My dog loved it too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia S. [](https://www.expedia.ca/Wilmington-Hotels-Cottage-In-The-Woods-With-A-Firepit.h91076053.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101650000/101640900/101640818/3316116c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101650000/101640900/101640818/a6271910.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101650000/101640900/101640818/79e77e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101650000/101640900/101640818/660335af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Chester [](https://www.expedia.ca/Chester-Hotels-2022-Rockingham-Old-House-Award-1840s-Cozy-Stone-Cottage.h101640818.Hotel-Information) 10/10 Exceptional (20 reviews) "The house is absolutely beautiful - Check in super easy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn J. [](https://www.expedia.ca/Chester-Hotels-2022-Rockingham-Old-House-Award-1840s-Cozy-Stone-Cottage.h101640818.Hotel-Information) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93602800/93602760/c3554443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93602800/93602760/15e96554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93602800/93602760/d9caaf2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93610000/93602800/93602760/bb3131b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Whitingham [](https://www.expedia.ca/Whitingham-Hotels-Family-Winter-Retreat-W-Hot-Tub-14-Mi-To-Slopes.h93602760.Hotel-Information) [](https://www.expedia.ca/Whitingham-Hotels-Family-Winter-Retreat-W-Hot-Tub-14-Mi-To-Slopes.h93602760.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409611/378bf69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409611/165c40e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409611/404434ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/103000000/102410000/102409700/102409611/83d35a92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Rare-New-Home-On-Lake-Whitingham-Semi-Priv-Beach.h102409611.Hotel-Information) 10/10 Exceptional (6 reviews) "Very nice place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael r. [](https://www.expedia.ca/Wilmington-Hotels-Rare-New-Home-On-Lake-Whitingham-Semi-Priv-Beach.h102409611.Hotel-Information) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992891/5b3b4b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992891/92f1fe50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992891/c5b64df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992891/c97de04e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Expansive-Grand-Estate-10-Mi-To-Mt-Snow.h119992891.Hotel-Information) 10/10 Exceptional (1 review) "Great winter gateaway at the mountains, close to mount snow, closed garage, lots of space and an authentic Vermont house. Indoor garage." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sahin [](https://www.expedia.ca/Wilmington-Hotels-Expansive-Grand-Estate-10-Mi-To-Mt-Snow.h119992891.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) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572765/5bcfe9a3.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) ### Cottage in Brattleboro [](https://www.expedia.ca/Brattleboro-Hotels-Cozy-Falls-Brook-Cabin-Hike-Swim-On-Site.h93572765.Hotel-Information) 10/10 Exceptional (2 reviews) "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) ![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/e8e49a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/620f7707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/413e13e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/070f19a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Jamaica [](https://www.expedia.ca/Jamaica-Hotels-Cozy-Cottage-7min-To-Ski-Stratton-Wood-Stove.h108495123.Hotel-Information) 10/10 Exceptional (3 reviews) "Nice and cozy, just like the listing shows. Great host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kytalia B. [](https://www.expedia.ca/Jamaica-Hotels-Cozy-Cottage-7min-To-Ski-Stratton-Wood-Stove.h108495123.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99800000/99795000/99794982/70798b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99800000/99795000/99794982/7d22c085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99800000/99795000/99794982/3b49748b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99800000/99795000/99794982/1f0debcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Putney [](https://www.expedia.ca/Putney-Hotels-Charming-Putney-Home-Porch.h99794982.Hotel-Information) [](https://www.expedia.ca/Putney-Hotels-Charming-Putney-Home-Porch.h99794982.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456949/074eaa29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456949/f1490737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456949/81544f9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124460000/124457000/124456949/68f13d4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in West Dover [](https://www.expedia.ca/West-Dover-Hotels-3-Mi-To-Mount-Snow-Spacious-West-Dover-Home.h124456949.Hotel-Information) [](https://www.expedia.ca/West-Dover-Hotels-3-Mi-To-Mount-Snow-Spacious-West-Dover-Home.h124456949.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116530000/116526400/116526328/6b9f4763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116530000/116526400/116526328/a212c0fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116530000/116526400/116526328/395615ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/117000000/116530000/116526400/116526328/d9f1c93d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in West Wardsboro [](https://www.expedia.ca/West-Wardsboro-Hotels-Home-2-Mi-To-Mt-Snow-Ski.h116526328.Hotel-Information) [](https://www.expedia.ca/West-Wardsboro-Hotels-Home-2-Mi-To-Mt-Snow-Ski.h116526328.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103710000/103706100/103706003/1b606ef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103710000/103706100/103706003/3c96e0bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/104000000/103710000/103706100/103706003/9d7d7fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103710000/103706100/103706003/1733ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in West Dover [](https://www.expedia.ca/West-Dover-Hotels-Cottage-In-Private-Village-On-VT-100.h103706003.Hotel-Information) 9.0/10 Wonderful (2 reviews) "I loved our stay here! The place is incredibly cozy. It’s in a fantastic location with great dining options just a few miles away. Plus, there are several nearby hiking trails with stunning views. Perfect for anyone looking to enjoy great food and outdoor adventures. Highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anicia K. [](https://www.expedia.ca/West-Dover-Hotels-Cottage-In-Private-Village-On-VT-100.h103706003.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113670000/113662500/113662475/1a7ff502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113670000/113662500/113662475/40e01a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113670000/113662500/113662475/ea7111f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/114000000/113670000/113662500/113662475/899180e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in West Dover [](https://www.expedia.ca/West-Dover-Hotels-Ski.h113662475.Hotel-Information) [](https://www.expedia.ca/West-Dover-Hotels-Ski.h113662475.Hotel-Information) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93550000/93548200/93548124/0ac0e5a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548200/93548124/039a0b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93550000/93548200/93548124/0eb48daa.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) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Wilmington-Home-On-18-Acres-9-Mi-To-Skiing.h93548124.Hotel-Information) 10/10 Exceptional (1 review) [](https://www.expedia.ca/Wilmington-Hotels-Wilmington-Home-On-18-Acres-9-Mi-To-Skiing.h93548124.Hotel-Information) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572800/e40ea591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572800/1da83c8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572800/c4ea86b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93580000/93572800/93572800/21465d7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Jacksonville [](https://www.expedia.ca/Jacksonville-Hotels-Johns-Farmhouse-In-Mount-Snow-On-120-Acres.h93572800.Hotel-Information) 10/10 Exceptional (1 review) "Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey [](https://www.expedia.ca/Jacksonville-Hotels-Johns-Farmhouse-In-Mount-Snow-On-120-Acres.h93572800.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554800/98554747/4f2707a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554800/98554747/0d4a793b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554800/98554747/a99e9b83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/99000000/98560000/98554800/98554747/0df51781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Wilmington-Vacation-Rental-Near-Hiking-And-Skiing.h98554747.Hotel-Information) [](https://www.expedia.ca/Wilmington-Hotels-Wilmington-Vacation-Rental-Near-Hiking-And-Skiing.h98554747.Hotel-Information) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/95000000/94360000/94353100/94353083/fa97721e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353100/94353083/69a5edad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353100/94353083/50414f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353100/94353083/b25646e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Jacksonville [](https://www.expedia.ca/Jacksonville-Hotels-Jacksonville-Cabin-W-Wraparound-Deck-Views.h94353083.Hotel-Information) [](https://www.expedia.ca/Jacksonville-Hotels-Jacksonville-Cabin-W-Wraparound-Deck-Views.h94353083.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353163/525550e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353163/fb94f8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353163/e47c2698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94360000/94353200/94353163/694a6032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Charming-Wilmington-Cabin.h94353163.Hotel-Information) 10/10 Exceptional (1 review) "The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark [](https://www.expedia.ca/Wilmington-Hotels-Charming-Wilmington-Cabin.h94353163.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992885/2b7d6dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992885/f9dc93d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992885/0c2da64d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/120000000/119992900/119992885/8a0886af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-2-Mi-To-Golfing-Hiking-Spacious-Wilmington-Home.h119992885.Hotel-Information) 10/10 Exceptional (2 reviews) "This place was absolutely perfect, very clean and very well taken care of." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles [](https://www.expedia.ca/Wilmington-Hotels-2-Mi-To-Golfing-Hiking-Spacious-Wilmington-Home.h119992885.Hotel-Information) ![House (4 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122340000/122331700/122331646/420c5888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122340000/122331700/122331646/8f7c2720.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122340000/122331700/122331646/f9714aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122340000/122331700/122331646/9169fe70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Pikes Falls [](https://www.expedia.ca/Jamaica-Hotels-Luxe-5.h122331646.Hotel-Information) [](https://www.expedia.ca/Jamaica-Hotels-Luxe-5.h122331646.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94954300/94954272/66dfd92f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94954300/94954272/838f05a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94954300/94954272/259e28bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/95000000/94960000/94954300/94954272/207b1ce5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Wilmington [](https://www.expedia.ca/Wilmington-Hotels-Peaceful-Marlboro-Vacation-Rental-W-Sauna-Yard.h94954272.Hotel-Information) [](https://www.expedia.ca/Wilmington-Hotels-Peaceful-Marlboro-Vacation-Rental-W-Sauna-Yard.h94954272.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=2026-03-17&endDate=2026-03-18®ionId=6057353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_6057353) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APART_HOTEL) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CHALET) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=CONDO) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=APARTMENT) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=COTTAGE) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-05-31&d1=2026-05-31&endDate=2026-06-03&d2=2026-06-03&lodging=VILLA) ![](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%2FWindham-County-Cottages.d6057353-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-County-Cottages.d6057353-aaCottages.Travel-Guide-Accommodation) ## Top Windham County Hotel Reviews ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "Staff was very courteous. The hot soup in the lobby was a nice touch! Loved the breakfast selections. " [](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Farm Road Estate](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/4a7d2d8e_y.jpg) ### Farm Road Estate 10/10 Excellent "Very clean room, all the necessary amenities in the room, comfortable bed, etc. Staff very friendly and helpful!" [](https://expedia.ca/West-Dover-Hotels-Farm-Road-Estate.h88730696.Hotel-Information) ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "My room was clean and spacious. Bed was very comfortable. Mini fridge and microwave a big plus! I normally stay at a different hotel when I come up to visit my family but I decided to try this hotel. I wasn't sure how it would be but I was pleasantly surprised! Clean, quiet and the gentleman who always seems to be at the front desk.. I'm sorry I can't remember his name is awesome! I was there for 3 weeks and I loved it! 10/10" [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg) ### Hideaway Inn Mt. Snow 10/10 Excellent "Very clean throughout. Great common areas with thoughtful amenities like games, chairs for eating takeout, and the best coffee/hot chocolate machine! " [](https://expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.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 "Good location for our needs and very comfortable" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Staff and clean room" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Big Bears Lodge](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108_y.jpg) ### Big Bears Lodge 10/10 Excellent "Nice big rooms , very clean, good breakfast, outdoor hot tub, everything you need for a ski holiday stay " [](https://expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) ![Kitzhof Inn](https://images.trvl-media.com/lodging/13000000/12030000/12026600/12026510/ffba9625_y.jpg) ### Kitzhof Inn 10/10 Excellent "We stayed there several times. The hospitality is fabulous. The breakfast every morning is delicious and plenty of food. Has plenty of room for their guests to hang out in the lodge with a fireplace and TV." [](https://expedia.ca/West-Dover-Hotels-Kitzhof-Inn.h12026510.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Good people working hard to offer a respectable stay" [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ## Find out more about Windham County ## Windham County Cottages information | Number of reviews | 102 | | ----------------- | ----------- | | Accommodation | 97 Cottages | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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) - [B&B in Brookline ](https://www.expedia.ca/Brookline-Bed-And-Breakfast.d3000459594-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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