Title: Book the Best Plymouth WINERY Hotels in 2025 | Expedia.ca [Hotels in Plymouth](https://expedia.ca/Plymouth-Hotels.d146918.Travel-Guide-Hotels)[Vacation Rentals in Plymouth](https://expedia.ca/Plymouth-Vacation-Rentals.d146918.Travel-Guide-VacationRentals)[Plymouth Car Rentals](https://expedia.ca/Car-Rentals-In-Plymouth.d146918.Car-Rental-Guide)[Plymouth Vacation Packages](https://expedia.ca/Plymouth.d146918.Destination-Travel-Guides) ![Central Vermont showing a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94646-Calvin-Coolidge-Historic-Site.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Plymouth, VT from CA $234 ![](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 Plymouth Winery Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=146918&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=146918&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=146918&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=146918&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Plymouth Winery Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/a1626ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/3794da32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/w1536h1021x0y3-8fc8ac6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/411cc5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Room in Historic Inn! 20 Minutes to Okemo! Chester Depot 9.2/10 Wonderful (16) "My stay was brief but was pleased to arrive to beautiful building and a room that was huge, well decorated/furnished, well heated, and super cozy. I would definitely stay here again." CA $139 CA $234 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96870000/96869100/96869045/b613b883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96870000/96869100/96869045/1cbbd1fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96870000/96869100/96869045/aaecd854.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/97000000/96870000/96869100/96869045/8b7d2e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OKEMO WINTERPLACE Best Location, Ski-In/Ski-Out 4BR/3BATH + LOFT. Spacious. Okemo Village 10/10 Exceptional (12) "The condo is great for ski in ski out" CA $560 CA $1,041 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Ludlow-Hotels-OKEMO-WINTERPLACE-Best-Location.h96869045.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/5f7ca819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w2000h1332x0y1-debdc5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1997h1332x0y1-cf8b4dbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w2000h1332x0y1-0e7bd3c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Double Bed Standard Hotel Room with outdoor heated pool 101 Killington 8.2/10 Very good (17) "Room was just right for our 2 day ski trip to Killington. 5 minutes from gondola lift & access to the entire mountain. Plenty of food options close by also. Heated pool was an added bonus! A 12 year veteran was in agreement." CA $161 CA $239 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-101.h38196993.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1999h1332x1y1-4b045cbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1996h1332x1y1-a0b4d4c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/1b255611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413501/w1997h1332x0y1-df9edd8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Queen Studio on the 2nd floor with outdoor heated pool 207 Killington 8.0/10 Very good (6) "Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail... CA $161 CA $238 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Queen-Studio-On-The-2nd-Floor-With-Outdoor-Heated-Pool-207.h38413501.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/39000000/38810000/38809700/38809634/w1999h1332x1y1-53bb15e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38810000/38809700/38809634/b5b9a196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books, offices](https://images.trvl-media.com/lodging/39000000/38810000/38809700/38809634/w2000h1332x0y1-30949f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38810000/38809700/38809634/w2000h1332x0y1-ad2d0122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21416 Killington 10/10 Exceptional (2) "The location was great for our trip. The condo was very clean." CA $221 CA $318 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Killington-Hotels-Deluxe-One-Bedroom-Suite-Located-On-2nd-Floor-With-Outdoor-Heated-Pool-21416.h38809634.Hotel-Information) ![TV, books, offices](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w1999h1332x1y1-80a57fa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/6e051916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w1996h1332x1y1-5da35f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w1999h1332x1y1-cf6d1a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Queen Bed Standard Hotel room with outdoor heated pool 201 Killington 8.6/10 Excellent (12) "Our room was easy to find and very clean. And the late check-in was very helpful." CA $161 CA $239 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Killington-Hotels-Two-Queen-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-201.h38412298.Hotel-Information) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/w1999h1332x1y1-840fb6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/w1999h1332x1y1-609774e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/w1999h1332x1y1-994c8c65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38830000/38825300/38825273/w2000h1332x0y1-8c82a951.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209 Killington 9.0/10 Wonderful (13) "Close to gondola!" CA $201 CA $291 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Killington-Hotels-Deluxe-One-Bedroom-Queen-Suite-On-The-2nd-Floor-With-Outdoor-Heated-Pool-209.h38825273.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412272/w1999h1332x1y1-3591be40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412272/w1999h1332x1y1-57d6641c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412272/bdc150eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412272/w1999h1332x1y1-0ad65e17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe One bedroom Queen Suite with outdoor heated pool 203 Killington 9.4/10 Exceptional (10) "Condo was clean & well furnished. Only stayed one night after a visit to Quechee, Woodstock, and area." CA $170 CA $251 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Killington-Hotels-Deluxe-One-Bedroom-Queen-Suite-With-Outdoor-Heated-Pool-203.h38412272.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412800/38412754/w1999h1332x1y1-8854bd14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412800/38412754/w1999h1332x1y1-f1b997d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38420000/38412800/38412754/w1997h1332x0y1-84fc2933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38412800/38412754/263149af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe one bedroom suite located on first floor with outdoor heated pool 11921 Killington 10/10 Exceptional (6) "We loved this area. The condo was exactly as described. We enjoyed the heated pool" CA $221 CA $318 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Killington-Hotels-Deluxe-One-Bedroom-Suite-Located-On-First-Floor-With-Outdoor-Heated-Pool-11921.h38412754.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/w1999h1332x1y1-7c92b6d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/w2000h1332x0y1-357770bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/w1997h1332x0y1-e0e1a851.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44450000/44445200/44445156/f58cecfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cedarbrook Hotel Room 2 Doubles 119 Killington 9.0/10 Wonderful (7) "The place was an ok place to "crash" after a day of out side activities. The rug needs to be replaced or shampooed. The beds are not very comfortable. " CA $161 CA $238 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Cedarbrook-Hotel-Room-W2-Doubles-119.h44445156.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=2025-10-30&endDate=2025-10-31®ionId=146918&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Plymouth Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Hotels near Bear Mountain Quad Ski Lift](https://www.expedia.ca/Bear-Mountain-Quad-Ski-Lift-Hotels.0-l6291422-0.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Belmont](https://www.expedia.ca/Belmont-Hotels-Pet-Friendly-Hotel.0-0-d553248635976386870-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Farmstay in Bridgewater](https://www.expedia.ca/Bridgewater-Agritourism.d553248635975851833-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Bridgewater](https://www.expedia.ca/Bridgewater-Apart-Hotels.d553248635975851833-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Bridgewater](https://www.expedia.ca/Bridgewater-Bed-And-Breakfast.d553248635975851833-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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[Camp Plymouth State Park](https://www.expedia.ca/Camp-Plymouth-State-Park-Plymouth.d6291265.Vacation-Attraction) - [K-1 Express Gondola](https://www.expedia.ca/K-1-Express-Gondola-Killington.d6291458.Vacation-Attraction) - [Killington Adventure Center](https://www.expedia.ca/Killington-Adventure-Center-Killington.d636717397721112576.Vacation-Attraction) - [Killington Golf Course](https://www.expedia.ca/Killington-Golf-Course-Killington.d6291063.Vacation-Attraction) - [Killington Peak](https://www.expedia.ca/Killington-Peak-Killington.d553248621563220980.Vacation-Attraction) - [Killington Resort](https://www.expedia.ca/Killington-Resort-Killington.d6082887.Vacation-Attraction) - [Ramshead Express Lift](https://www.expedia.ca/Ramshead-Express-Lift-Killington.d6291586.Vacation-Attraction) - [Snowdon Triple Ski Lift](https://www.expedia.ca/Snowdon-Triple-Ski-Lift-Killington.d6292030.Vacation-Attraction) - [Suv Car Rentals near Superstar Express Quad Ski Lift](https://www.expedia.ca/SUV-Car-Rentals-In-Superstar-Express-Quad-Ski-Lift.d6291646-tSUV.Car-Rental-Guide-Class) - [Things to do in Bridgewater Corners](https://www.expedia.ca/Things-To-Do-In-Bridgewater-Corners.d6357904.Travel-Guide-Activities) - [Book Winery Hotels in Plymouth on Expedia.com](https://www.expedia.com/Plymouth-Hotels-Winery-Hotel.0-0-d146918-tWineryHotel.Travel-Guide-Filter-Hotels)