Title: Book the Best SHOPPING Hotels in Chester in 2025 | 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Shopping Hotels in Chester, VT from CA $158 ![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 Chester Shopping Hotels Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chester Shopping Hotels ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/dd202f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/9ca0f525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/776c9b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (696) "Check in was easy and there is coffee available 24 hours a day!" CA $165 CA $181 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/1eab968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/b79a8982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro Brattleboro 8.2/10 Very good (894) "Clean room and great breakfast" CA $143 CA $158 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/94368990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/7679bd03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/351bbc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/fcb0767d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Toll Road Inn Manchester Center 9.0/10 Wonderful (476) "The room was very clean, and the beds were extremely comfortable. Would definitely stay there again. Coffee 24 hours a day, pool and hot tub. Highly recommend staying there." CA $195 CA $215 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Toll-Road-Inn.h7652200.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) ![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) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/3794da32.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 $138 CA $233 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/10b7883b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/2f37dfc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/367c70d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107010000/107005900/107005892/c07b5f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit Cavendish 10/10 Exceptional (7) "Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay" CA $260 CA $450 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Cavendish-Hotels-Luxury-Cabin-1-Hot-Tub.h107005892.Hotel-Information) ![Family Cabin | Living area](https://images.trvl-media.com/lodging/97000000/96610000/96600400/96600348/346ccbc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shared kitchen facilities](https://images.trvl-media.com/lodging/97000000/96610000/96600400/96600348/6779f030.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cabin | Living area](https://images.trvl-media.com/lodging/97000000/96610000/96600400/96600348/cededb40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cabin | Private kitchen](https://images.trvl-media.com/lodging/97000000/96610000/96600400/96600348/0e1c79b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Bound Inn Wilmington 9.4/10 Exceptional (10) "Great property. Amazing views!" CA $303 CA $334 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Wilmington-Hotels-441-Coldbrook-Rd.h96600348.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/22000000/21870000/21860900/21860884/e0f25183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, Multiple Beds, Garden View](https://images.trvl-media.com/lodging/22000000/21870000/21860900/21860884/54dc91bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21870000/21860900/21860884/3f8bde70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/22000000/21870000/21860900/21860884/cdd5f061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Main and Mountain Bar & Motel Ludlow 9.6/10 Exceptional (206) "Amazing place to stay " CA $285 CA $314 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Ludlow-Hotels-Main-And-Mountain-Bar-Motel.h21860884.Hotel-Information) ![Condo, 2 Bedrooms | Pool](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31db03a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/a16eeef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom | View from room](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31550a82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snow and ski sports](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/1e2b3992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Long Trail House at Stratton Mountain Resort Stratton 8.6/10 Excellent (74) "Nice, clean room in prime location" CA $443 CA $551 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/42aae2de.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) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/c114f9cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/43a87c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vantage Point Villas at Stratton Mountain Resort Stratton 8.4/10 Very good (67) "Beautiful place. I would stay here again if I could. " CA $311 CA $387 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Stratton-Hotels-Vantage-Point-Villas-At-Stratton-Mountain-Resort.h6602387.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/cd86c3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07d4fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/3e81c990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Inn & Resort Woodstock 9.2/10 Wonderful (534) "Clean room. Staff very polite and helpful " CA $571 CA $690 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.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=2025-10-17&endDate=2025-10-18®ionId=89014&adults=2&location_highlights_explore=shopping&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "The grounds around the hotel are beautiful. The rooms are very nice and comfortable. Paige the bartender is awesome. Breakfast was very good, highly recommend the skillet breakfast." [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](//images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Wonderful accommodation " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Hampton Inn and Suites Manchester](//images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "The staff was great!" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Very clean, up to date, affordable" [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "What a lovely delight near the New Hampshire/Vermont border! The staff is very welcoming, the room is beautiful and clean, and the sunrise/sunset on the river are remarkable! When I accidently left behind something precious, they were quick to send it to me. This is an overall gem of a hotel. " [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Comfortable place to stay " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Nice big room for the money " [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Kimpton Taconic Hotel by IHG](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/72cb9377_y.jpg) ### Kimpton Taconic Hotel by IHG 10/10 Excellent "Very nice, beautiful inn" [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.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) - 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[Resorts in Grafton](https://www.expedia.ca/Grafton-Resort-Hotels.d184049-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Magic Mountain Ski Resort](https://www.expedia.ca/Magic-Mountain-Ski-Resort-Hotels.0-l6115886-0.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in North Springfield](https://www.expedia.ca/North-Springfield-Hotels-Pet-Friendly-Hotel.0-0-d184061-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in North Springfield](https://www.expedia.ca/North-Springfield-Hotels-Spa-Hotel.0-0-d184061-tSpaHotel.Travel-Guide-Filter-Hotels) - [North Springfield Hotels](https://www.expedia.ca/North-Springfield-Hotels.d184061.Travel-Guide-Hotels) - [Resorts in North Springfield](https://www.expedia.ca/North-Springfield-Resort-Hotels.d184061-aaResortHotels.Travel-Guide-Accommodation) - [Castles in Proctorsville](https://www.expedia.ca/Proctorsville-Castles.d6023678-aaCastles.Travel-Guide-Accommodation) - [Honeymoon Resorts and in Proctorsville](https://www.expedia.ca/Proctorsville-Hotels-Honeymoon-Hotels.0-0-d6023678-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - 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[Springfield Hotels](https://www.expedia.ca/Springfield-Hotels.d10292.Travel-Guide-Hotels) - [Resorts in Springfield](https://www.expedia.ca/Springfield-Resort-Hotels.d10292-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Vermont Country Store](https://www.expedia.ca/Vermont-Country-Store-Hotels.0-l553248621532666908-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Weston](https://www.expedia.ca/Weston-Hotels-Business-Hotel.0-0-d177460-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Weston](https://www.expedia.ca/Weston-Hotels-Luxury-Hotel.0-0-d177460-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [B&B in Windham](https://www.expedia.ca/Windham-Bed-And-Breakfast.d6150553-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Windham](https://www.expedia.ca/Windham-Hotels-Couples-Resorts-Hotels.0-0-d6150553-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Windham Hotels](https://www.expedia.ca/Windham-Hotels.d6150553.Travel-Guide-Hotels) - [Resorts in Windham](https://www.expedia.ca/Windham-Resort-Hotels.d6150553-aaResortHotels.Travel-Guide-Accommodation) - [Flights from Springfield](https://www.expedia.ca/lp/flights/10292/flights-from-springfield) - [Flights from Grafton](https://www.expedia.ca/lp/flights/184049/flights-from-grafton) - [Flights from Columbia (CAE) to Springfield (VSF)](https://www.expedia.ca/lp/flights/cae/vsf/columbia-to-springfield) - [Flights from Charlotte (CLT) to Springfield (VSF)](https://www.expedia.ca/lp/flights/clt/vsf/charlotte-to-springfield) - [Flights from Wilmington (ILM) to Springfield (VSF)](https://www.expedia.ca/lp/flights/ilm/vsf/wilmington-to-springfield) - [Flights from Minneapolis (MSP) to Springfield (VSF)](https://www.expedia.ca/lp/flights/msp/vsf/minneapolis-to-springfield) - [Flights from Ottawa (YOW) to Springfield (VSF)](https://www.expedia.ca/lp/flights/yow/vsf/ottawa-to-springfield) - [Andover Vacations](https://www.expedia.ca/Andover.d6023580.Destination-Travel-Guides) - [Visit Andover](https://www.expedia.ca/Andover.dx6023580) - [Fletcher Farm School for the Arts and Crafts](https://www.expedia.ca/Fletcher-Farm-School-For-The-Arts-And-Crafts-Ludlow.d553248621532666921.Vacation-Attraction) - [Vermont Country Store](https://www.expedia.ca/Vermont-Country-Store-Bellows-Falls.d553248621532666908.Vacation-Attraction) - [Visit Weston](https://www.expedia.ca/Weston.dx177460) - [Car rental Grafton](https://www.expedia.ca/Car-Rentals-In-Grafton.d184049.Car-Rental-Guide) - [Car rental Windham](https://www.expedia.ca/Car-Rentals-In-Windham.d6150553.Car-Rental-Guide)