Title: Book the Best South Shaftsbury LUXURY Hotels - Upscale Hotels in South Shaftsbury, VT | Expedia.ca [Hotels in South Shaftsbury](https://expedia.ca/South-Shaftsbury-Hotels.d553248634999160873.Travel-Guide-Hotels)[Vacation Rentals in South Shaftsbury](https://expedia.ca/South-Shaftsbury-Vacation-Rentals.d553248634999160873.Travel-Guide-VacationRentals)[South Shaftsbury Car Rentals](https://expedia.ca/Car-Rentals-In-South-Shaftsbury.d553248634999160873.Car-Rental-Guide)[South Shaftsbury Vacation Packages](https://expedia.ca/South-Shaftsbury.d553248634999160873.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/luxury.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in South Shaftsbury, VT - ![](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 South Shaftsbury Luxury Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=553248634999160873&startDate=2025-12-11&endDate=2025-12-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248634999160873&startDate=2025-12-12&endDate=2025-12-13&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248634999160873&startDate=2025-12-12&endDate=2025-12-14&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248634999160873&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for South Shaftsbury luxury hotels ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/2544c235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Dorset)](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/4eb135c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (Farm House) | Private kitchen](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/30a5bc87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/2f26bb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hill Farm Inn [](https://www.expedia.ca/Bennington-Hotels-Hill-Farm-Inn.h1502179.Hotel-Information) Arlington 9.6/10 Exceptional (173) "This Inn is spectacular! The rooms, grounds, decor, staff and restaurant all were the best for stops on our vacation." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $234 CA $565 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Bennington-Hotels-Hill-Farm-Inn.h1502179.Hotel-Information) ![Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/a1fa9bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/d62d499f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/2cf52cb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/e72452e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Four Chimneys Inn [](https://www.expedia.ca/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information) Bennington 9.4/10 Exceptional (280) "What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon [](https://www.expedia.ca/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/fddae827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/4b2f1194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/e0c2a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Equinox Golf Resort & Spa [](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) Manchester Village Historic District 7.4/10 Good (576) "Beautiful hotel! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sarah CA $260 CA $364 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Deluxe Room](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/8359157a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/190c1179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/47528d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/4000000/3910000/3908500/3908442/b891aa86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Reluctant Panther Inn and Restaurant [](https://www.expedia.ca/Bennington-Hotels-The-Reluctant-Panther-Inn-And-Restaurant.h3908442.Hotel-Information) Manchester Village Historic District 9.8/10 Exceptional (331) "Wonderful stay! The room was spacious and the bed was heaven. The breakfast was amazing and they were even able to offer gluten free options!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abbie CA $247 CA $271 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Bennington-Hotels-The-Reluctant-Panther-Inn-And-Restaurant.h3908442.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/c60f19d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) Williamstown 9.6/10 Exceptional (549) "Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jon CA $255 CA $285 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/0f420ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/a975c57b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/a0178b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/84448130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### South Shire [](https://www.expedia.ca/Bennington-Hotels-South-Shire.h76163190.Hotel-Information) Bennington 9.2/10 Wonderful (118) "Great period decor! Spacious rooms and an inviting living room to relax. Also walking distance to downtown shops and restaurants was a real plus!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roseann CA $225 CA $261 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Bennington-Hotels-South-Shire.h76163190.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/a88566dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/e86f622b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, minibar, in-room safe](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/55f5385b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kimpton Taconic Hotel by IHG [](https://www.expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) Manchester Village Historic District 9.4/10 Exceptional (817) "Very nice, beautiful inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $233 CA $310 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/a85c8ad4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/453cecd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/a22d6eb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/75000000/74250000/74248400/74248370/726c249b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hermitage Inn Vermont [](https://www.expedia.ca/West-Dover-Hotels-The-Hermitage-Inn-Vermont.h74248370.Hotel-Information) West Dover 9.2/10 Wonderful (15) "Great stay,beautiful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vibhavasu [](https://www.expedia.ca/West-Dover-Hotels-The-Hermitage-Inn-Vermont.h74248370.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=2025-12-26&endDate=2025-12-27®ionId=553248634999160873&adults=2&sort=LUXURY&star=50&openPlayBack=true) ## Top South Shaftsbury Hotel Reviews ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Hot tub was relaxing. Parking was easy. Restaurant within walking distance. If you forget anything dollar general close." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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 "Complimentary breakfast was nice. Room was clean. " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg) ### Hampton Inn Bennington 10/10 Excellent "Yes" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "My room was so big! Very clean, huge bathroom, claw foot tub. Highly recommend this place. It had a great vibe. Was not industrial like a hotel, had a very clean and comforting feeling, like you were visiting a relative. I stayed here for my brother’s wedding at MoCA. Great experience all around. Definitely will be back. " [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Courteous staff Clean room" [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to South Shaftsbury? ### When can I expect good weather in South Shaftsbury? ### What's there to see and do in South Shaftsbury? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - 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) - 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