Title: Book the Best Bennington WINERY Hotels in 2025 | Expedia.ca [Hotels in Bennington](https://expedia.ca/Bennington-Hotels.d6057349.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.ca/Bennington-Vacation-Rentals.d6057349.Travel-Guide-VacationRentals)[Flights to Bennington](https://expedia.ca/Cheap-Flights-To-Bennington.d6057349.Travel-Guide-Flights)[Things to do in Bennington](https://expedia.ca/Things-To-Do-In-Bennington.d6057349.Travel-Guide-Activities)[Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Bennington.d6057349.Car-Rental-Guide)[Bennington Vacation Packages](https://expedia.ca/Bennington.d6057349.Destination-Travel-Guides) ![Bennington Battle Monument featuring landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94635-Bennington-Battle-Monument.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Bennington, VT from CA $257 ![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 Bennington Winery Hotels Tonight [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-09-23&endDate=2025-09-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-09-24&endDate=2025-09-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Bennington Winery Hotels ![Desk, blackout drapes, soundproofing, free WiFi](https://images.trvl-media.com/lodging/2000000/1160000/1157400/1157354/3e494820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1160000/1157400/1157354/ab563a6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1160000/1157400/1157354/3e7e09df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1160000/1157400/1157354/8545d38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Lodge Bromley Mountain 8.6/10 Excellent (285) "Awesome food and area " CA $257 CA $280 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Bennington-Hotels-The-Lodge-At-Bromley.h1157354.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505813/d85c3b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Martin Chester's Room](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505813/520076d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505813/009cefa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505813/4d5f7b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Arlington Inn Arlington 8.8/10 Excellent (177) "Great service and really great breakfast " CA $279 CA $304 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Bennington-Hotels-Arlington-Inn.h1505813.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/78b361f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/16c514f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/15c28efa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Triple Room](https://images.trvl-media.com/lodging/1000000/900000/894100/894066/648d8aa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Valley Inn Williamstown 9.2/10 Wonderful (561) "Beautiful property, wonderful staff, great breakfast. " CA $230 CA $257 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Williamstown-Hotels-Berkshire-Valley-Inn.h894066.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/2bddc33a.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) "The room was fine. Bright night lights outside require eye masks for dark sleeping. The shower unit was a bit odd… not a conventional shower stall. The bottom fitted sheet did not stay on the mattress." CA $206 CA $317 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/be6cf63b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/5df4ccf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/588d6d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/97000000/96220000/96211300/96211209/3cf333b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Escape! Jamaica 9.8/10 Exceptional (18) "Easy booking, clean home, great location and the owner very easy to get in touch with." CA $315 CA $965 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bondville-Hotels-The-Mountain-Escape.h96211209.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/626fc277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/0e44f29d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/31bb0c4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/77000000/76910000/76905900/76905876/6945d27e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Oasis - Hot Tub, Sauna, Fire Pit, & MORE! Jamaica 9.8/10 Exceptional (27) "EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)." CA $893 CA $1,712 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Bondville-Hotels-Mountain-Oasis-Hot-Tub.h76905876.Hotel-Information) ![Panoramic House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/6511d75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/3358f5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House | Private kitchen](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/f721b80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic House](https://images.trvl-media.com/lodging/84000000/83790000/83780800/83780792/106aa7f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Brooks Lodge Bennington 4.8/10 (3) "Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've... CA $157 CA $344 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Bennington-Hotels-Two-Brooks-Lodge.h83780792.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/89954d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/c71f56f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/f59a163f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/7665cd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House Dover 9.6/10 Exceptional (19) "We had an amazing trip, and the host was very responsive and helpful with everything. The house was great, had everything we needed, and the private ski run back to the property was really fun. Highly recommend this property and the best host we have ever had!! Favoriting this place for a future stay!" CA $116 CA $505 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6ba9f20d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/516bcaba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/7ec1e2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eca16f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed Whitingham 10/10 Exceptional (14) "Great property, plenty of space and room for all. Location is ideal" CA $341 CA $763 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/a2eafec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/c26da9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/083f8263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/3a874a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 minutes to Mount Snow, Dog Friendly, Fire Pit, Hot Tub, Game Room, Private West Dover 10/10 Exceptional (20) "Whole hearted recommend this property for anyone looking to stay in the area. Great location, great atmosphere and most importantly great house. 10/10 hidden gem. " CA $325 CA $948 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.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=2025-10-08&endDate=2025-10-09®ionId=6057349&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Bennington Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in West Arlington](https://www.expedia.ca/4Star-West-Arlington-Hotels.s40-0-d553248635976385881.Travel-Guide-Filter-Hotels) - [B&B in Arlington](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d74695-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hostels in Arlington](https://www.expedia.ca/Arlington-Hostels.d74695-aaHostels.Travel-Guide-Accommodation) - [Boutique Hotels in Arlington](https://www.expedia.ca/Arlington-Hotels-Boutique-Hotel.0-0-d74695-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Arlington](https://www.expedia.ca/Arlington-Hotels-Hotel-With-Pool.0-0-d74695-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Arlington](https://www.expedia.ca/Arlington-Hotels-Pet-Friendly-Hotel.0-0-d74695-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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[Sunderland Hotels](https://www.expedia.ca/Sunderland-Hotels.d6324879.Travel-Guide-Hotels) - [Apartments in West Arlington](https://www.expedia.ca/West-Arlington-Apartments.d553248635976385881-aaApartments.Travel-Guide-Accommodation) - [B&B in Woodford](https://www.expedia.ca/Woodford-Bed-And-Breakfast.d553248635975848582-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Woodford](https://www.expedia.ca/Woodford-Guest-Houses.d553248635975848582-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Woodford](https://www.expedia.ca/Woodford-Hotels-Cheap-Hotels.0-0-d553248635975848582-tCheapHotels.Travel-Guide-Filter-Hotels) - [Woodford Hotels](https://www.expedia.ca/Woodford-Hotels.d553248635975848582.Travel-Guide-Hotels) - [Inns in Woodford](https://www.expedia.ca/Woodford-Inns.d553248635975848582-aaInns.Travel-Guide-Accommodation) - [Lodges in Woodford](https://www.expedia.ca/Woodford-Lodges.d553248635975848582-aaLodges.Travel-Guide-Accommodation) - [Motels in Woodford](https://www.expedia.ca/Woodford-Motels.d553248635975848582-aaMotels.Travel-Guide-Accommodation) - 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[Suv Car Rentals near Warlock's Woods](https://www.expedia.ca/SUV-Car-Rentals-In-Warlocks-Woods.d553248635996618389-tSUV.Car-Rental-Guide-Class) - [Book Winery Hotels in Bennington on Expedia.com](https://www.expedia.com/Bennington-Hotels-Winery-Hotel.0-0-d6057349-tWineryHotel.Travel-Guide-Filter-Hotels)