Title: Book the Best Hotels with POOL 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 Hotels with a Pool in Chester, VT from CA $163 - ![](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 Hotels with a Pool Tonight [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-29&endDate=2025-12-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-30&endDate=2025-12-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels with a pool ![Exterior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/0b98ffc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/4b878d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/100000000/99880000/99874800/99874704/8d67161d.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 $308 CA $733 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Chester-Hotels-Historic-150-Year-Old-Farmhouse.h99874704.Hotel-Information) ![Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c8df49db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/d5eb5082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Studio Suite](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/79903cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Studio Suite](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/2f60e9cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hideaway Inn Mt. Snow [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) West Dover 10/10 Exceptional (6) "Clean rooms/ close to mountain/ nice experience" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Morgan CA $180 CA $199 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/322811f5.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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/32bcc2b6.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 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) Brattleboro 8.6/10 Excellent (748) "Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jack CA $166 CA $182 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/46351656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/ac65fd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/8582bd1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield Hotel [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) Springfield 8.8/10 Excellent (808) "The staff were very friendly; the breakfast was awesome. the pool was heated just right, and the room was very clean, I will stay here again. Good job Best western," ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose CA $208 CA $229 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/95e5b046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/211acecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/8ffbb75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Elm City Hotel, an Ascend Collection Hotel [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) Keene 8.4/10 Very good (969) "Staff was very welcoming and the room was very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $170 CA $184 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/b79a8982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/f3cee559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) Brattleboro 8.2/10 Very good (928) "The room was very clean, and both staff and service were outstanding." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wonji CA $201 CA $221 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Indoor pool, open 6:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3840h2556x0y4-fbdd8b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-dbaacfef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) Keene 8.4/10 Very good (1001) "Great staff, clean room, nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DORTHY CA $190 CA $206 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/058b0dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/2680e185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/707e42f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/e51d292e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) Brattleboro 8.8/10 Excellent (1001) "Very clean room, gentlemen at the front desk were welcoming and professional and the coffee was amazing! We are frequent visitors with you; we love IHG hotels. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Belinda CA $197 CA $217 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/96a629e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/1d2c94d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/w776h446x0y3-b969a7b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pointe at Castle Hill Resort [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) Cavendish 8.8/10 Excellent (936) "Great place to stay while skiing at okemo" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken CA $187 CA $214 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/bbdb2e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/a961b35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/7abf75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/d0dd0859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Keene [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) Keene 8.8/10 Excellent (360) "Clean comfy nice staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine CA $231 CA $251 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.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=2026-01-12&endDate=2026-01-13®ionId=89014&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Very helpful staff, good folks." [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.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 "Nice experience. Great location, good property, excellent service and care taking" [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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 "Spectular continental breakfast and really nice staff. Room was clean and beautiful. Amazing stay overall!" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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 "10/10 Perfect Stay. So accommodating and kind staff. " [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![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 "Staff are exceptionally friendly and helpful " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg) ### Woodstock Inn & Resort 10/10 Excellent "Luxurious and friendly resort! Loved it" [](https://expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.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 "Place definitely needs some updating but it was clean and the staff was great!" [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.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 "Super responsive staff, great accomodations " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.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) ## Frequently asked questions ### What are some hotels with pools in Chester? ### What is there to see and do in Chester? ### When is the best time to book a hotel with a pool in Chester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [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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