Title: Book the Best Woodstock WINERY Hotels in 2025 | Expedia.ca [Woodstock Travel Guide](https://expedia.ca/Woodstock.dx10868)[Hotels in Woodstock](https://expedia.ca/Woodstock-Hotels.d10868.Travel-Guide-Hotels)[Vacation Rentals in Woodstock](https://expedia.ca/Woodstock-Vacation-Rentals.d10868.Travel-Guide-VacationRentals)[Things to do in Woodstock](https://expedia.ca/Things-To-Do-In-Woodstock.d10868.Travel-Guide-Activities)[Woodstock Car Rentals](https://expedia.ca/Car-Rentals-In-Woodstock.d10868.Car-Rental-Guide)[Woodstock Vacation Packages](https://expedia.ca/Woodstock.d10868.Destination-Travel-Guides) ![Woodstock showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94304-Woodstock.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Woodstock, VT from CA $263 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Woodstock Winery Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=10868&startDate=2025-09-27&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=10868&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=10868&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=10868&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Woodstock Winery Hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/12000000/11140000/11139700/11139607/48ac360b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/12000000/11140000/11139700/11139607/56e0207c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/12000000/11140000/11139700/11139607/d1ef9165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living room](https://images.trvl-media.com/lodging/12000000/11140000/11139700/11139607/015e8de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodbridge Inn Woodstock 9.6/10 Exceptional (66) "Staff was very friendly and welcoming " CA $647 CA $712 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Woodstock-Hotels-Woodbridge-Inn.h11139607.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/5fe23c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Room 2)](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/910cc1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/6ee6a37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1490000/1482700/1482698/e76d85b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deer Brook Inn Woodstock 10/10 Exceptional (21) "One of the best experiences I have ever had! The staff were kind, attentive, and just plain wonderful! I can't wait to return as soon as possible! This place is BEAUTIFUL inside and out! (Not to mention that the breakfast was to die for). Don't think twice- you need to stay at the Deer Brook Inn!" [](https://www.expedia.ca/Woodstock-Hotels-Deer-Brook-Inn.h1482698.Hotel-Information) ![Deluxe Suite](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/d5194d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Accessible, Dog-Friendly Double](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/53cc1cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/32c31fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Woodstock Motel Woodstock 9.6/10 Exceptional (522) "I come to area for medical visits often and Sleep Woodstock is my new favorite stay!" CA $218 CA $263 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![Family Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/29250062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/e090e64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On The River Inn West Woodstock 9.4/10 Exceptional (1002) "Great location, very quiet with good breakfast choices. " [](https://www.expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/91483dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jackson West Woodstock 9.8/10 Exceptional (234) "Excellent Vintage style B&B. " CA $306 CA $337 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.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=2025-10-11&endDate=2025-10-12®ionId=10868&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Woodstock Hotel Reviews ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Excellent Vintage style B&B. " [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Sleep Woodstock Motel](//images.trvl-media.com/lodging/10000000/9660000/9658900/9658860/7b3a7c11_y.jpg) ### Sleep Woodstock Motel 10/10 Excellent "Very hospitable and well appointed motel, 5 minute drive into woodstock. Very cute. spotlessly clean and had everything you couild need. Note - cannabis dispensary directly next door just FYI" [](https://expedia.ca/Woodstock-Hotels-Sleep-Woodstock-Motel.h9658860.Hotel-Information) ![On The River Inn](//images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/528a7f5b_y.jpg) ### On The River Inn 10/10 Excellent "Beautiful property with abundant amenities. Great for families in a wonderful location with plenty of activities and dining near by for any season. Will be back!" 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[Quechee Gorge Bridge](https://www.expedia.ca/Quechee-Gorge-Bridge-White-River-Junction.d6139298.Vacation-Attraction) - [Quechee Ski Hill](https://www.expedia.ca/Quechee-Ski-Hill-White-River-Junction.d6175207.Vacation-Attraction) - [Visit Quechee](https://www.expedia.ca/Quechee.dx9580) - [Visit South Woodstock](https://www.expedia.ca/South-Woodstock.dx6149659) - [Car rentals near Red Wagon Toy Company](https://www.expedia.ca/Car-Rentals-In-Red-Wagon-Toy-Company.d553248621532667633.Car-Rental-Guide) - [Quechee Vacation Rentals](https://www.expedia.ca/Quechee-Vacation-Rentals.d9580.Travel-Guide-VacationRentals) - [Book Winery Hotels in Woodstock on Expedia.com](https://www.expedia.com/Woodstock-Hotels-Winery-Hotel.0-0-d10868-tWineryHotel.Travel-Guide-Filter-Hotels)