Title: Book the Best SHOPPING Hotels in Chester in 2026 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides) ![aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Shopping Hotels in Chester, VT from CA $254 - ![](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 Chester Shopping Hotels Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels with shopping nearby ![Dining](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/1377c15b.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) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/f538976a.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) ### Room in Historic Inn! 20 Minutes to Okemo! [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.Hotel-Information) Chester Depot 9.2/10 Wonderful (18) "The Chester Inn was beautiful and located in downtown Chester. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter C. CA $165 CA $264 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/6a78e813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/fca309d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/5f7adde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/e4341991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic 150-year-old farmhouse, Jacuzzi included [](https://www.expedia.ca/Chester-Hotels-Historic-150-Year-Old-Farmhouse.h99874704.Hotel-Information) Chester Depot 9.8/10 Exceptional (10) "This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy S. CA $236 CA $646 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Chester-Hotels-Historic-150-Year-Old-Farmhouse.h99874704.Hotel-Information) ![Family dining](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/0712fd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/aa5bf8b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/c5d91be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/4ca53e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vantage Point Villas at Stratton Mountain Resort [](https://www.expedia.ca/Stratton-Hotels-Vantage-Point-Villas-At-Stratton-Mountain-Resort.h6602387.Hotel-Information) Stratton 8.4/10 Very good (70) "Amazing stay - The condo was cozy and perfect for our family! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate CA $395 CA $492 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Stratton-Hotels-Vantage-Point-Villas-At-Stratton-Mountain-Resort.h6602387.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w2000h1332x0y1-debdc5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/5f7ca819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1999h1332x1y1-dd061e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1999h1332x1y1-b15a3da9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Double Bed Standard Hotel Room with outdoor heated pool 101 [](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-101.h38196993.Hotel-Information) Killington 8.2/10 Very good (17) "Loved this lodging. Super fun outdoorsy place. Enjoyed the warm pool and grills and picnic table area. Liked the coffee in mornings in the office. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr Arun CA $174 CA $257 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-101.h38196993.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w2000h1332x0y1-ffd96318.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) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/6e051916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/39000000/38420000/38412300/38412298/w1999h1332x1y1-b3dcc7e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Queen Bed Standard Hotel room with outdoor heated pool 201 [](https://www.expedia.ca/Killington-Hotels-Two-Queen-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-201.h38412298.Hotel-Information) Killington 8.8/10 Excellent (13) "It was a great place for us to spend the night before continuing our travel up north to see the eclipse ☀️ " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucy Marshall CA $174 CA $254 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Killington-Hotels-Two-Queen-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-201.h38412298.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/73e1d55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w1125h1933x0y49-6292efb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly Hilltop House In Putney Vermont [](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) Putney 9.4/10 Exceptional (57) "The property was beautiful--great views, super peaceful, and fabulous hosts. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Louis T. CA $204 CA $390 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/c07b5f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/4623c2dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/10b7883b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/c678f87b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit [](https://www.expedia.ca/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.Hotel-Information) Cavendish 10/10 Exceptional (10) "Super easy check in, beautiful and peaceful. Will def be back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler S. CA $271 CA $463 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/fe04814b.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) ![Interior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/a1a0916f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/ef743cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly [](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information) West Dover 10/10 Exceptional (20) "Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeannine A. CA $192 CA $771 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information) ![Internet, bed sheets](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/9c3e040e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/59f11c9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/f4ee1a7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66050000/66042300/66042213/ff9fa2e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Efficient condo near slopes with kitchenette & great location [](https://www.expedia.ca/Ludlow-Hotels-Efficient-Condo-Near-Slopes-With-Kitchenette-Great-Location.h66042213.Hotel-Information) Ludlow 8.6/10 Excellent (32) "great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) C A. CA $131 CA $311 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Ludlow-Hotels-Efficient-Condo-Near-Slopes-With-Kitchenette-Great-Location.h66042213.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/f68608f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/005d9ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books, video library](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/15f78921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/22000000/21710000/21708500/21708413/e7a4fea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails [](https://www.expedia.ca/Ludlow-Hotels-Condo-With-Seasonal-Pool-Tennis-Courts-Walk-To-Ski-Trails.h21708413.Hotel-Information) Ludlow 7.6/10 Good (53) "Irish Bar nearby was a plus on St. Patrick’s Day !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Warren CA $98 CA $467 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Ludlow-Hotels-Condo-With-Seasonal-Pool-Tennis-Courts-Walk-To-Ski-Trails.h21708413.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=2025-12-28&endDate=2025-12-29®ionId=89014&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Yea" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Price, clean and spacious room, comfy bed." [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Clean room, very nice staff, everything was excellent! " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Staff were very friendly. The pool was the perfect temperature. Would definitely stay again. " [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.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) ![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/9c9da73f_y.jpg) ### The Palmer House Resort, an Ascend Collection Hotel 10/10 Excellent "Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! " [](https://expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "After reading reviews I was pleasantly surprised of the high quality of our room. We had a premium king room in the river house. Was large and bathroom was also large with a jacuzzi tub, shared balcony overlooking the river. Walking distance to town, shops and restaurants. Only stayed one night for a wedding in town but overall had a very good experience!" [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "Nice bar, comfortable lobby for meeting and greeting. Room was squeaky clean with great bed and shower. Love it here!" [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Excellent place to stay anytime of the year." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [B&B in Andover ](https://www.expedia.ca/Andover-Bed-And-Breakfast.d6023580-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Andover ](https://www.expedia.ca/Andover-Chalets.d6023580-aaChalets.Travel-Guide-Accommodation) - [Country Houses in Andover ](https://www.expedia.ca/Andover-Country-House.d6023580-aaCountryHouse.Travel-Guide-Accommodation) - [Andover Hotels ](https://www.expedia.ca/Andover-Hotels.d6023580.Travel-Guide-Hotels) - [Inns in Andover ](https://www.expedia.ca/Andover-Inns.d6023580-aaInns.Travel-Guide-Accommodation) - [Motels in Andover ](https://www.expedia.ca/Andover-Motels.d6023580-aaMotels.Travel-Guide-Accommodation) - [Resorts in Andover ](https://www.expedia.ca/Andover-Resort-Hotels.d6023580-aaResortHotels.Travel-Guide-Accommodation) - [Hotels with a Pool in Athens ](https://www.expedia.ca/Athens-Hotels-Hotel-With-Pool.0-0-d553248634998621896-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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