Title: The Best Chester, VT Chalets from $271 | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx89014)[Hotels in Chester](https://expedia.com/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d89014.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d89014.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=89014&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester chalets ![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/c71f56f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/e73412a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/26cdcbb4.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 [](https://www.expedia.com/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information) Dover 9.8/10 Exceptional (22 reviews) "Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SZU YIN C. $360 nightly $407 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/63238a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ba81a7b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/0c516aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/107000000/106160000/106157400/106157385/ad2f042c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington [](https://www.expedia.com/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.Hotel-Information) Plymouth 10/10 Exceptional (14 reviews) "We had a great stay! Beautiful spot tucked in the woods. Great host communication!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie-Anne B. $592 nightly $663 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Plymouth-Hotels-BIGFOOT-CHALET.h106157385.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.com/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information) West Dover 10/10 Exceptional (23 reviews) "Wonderful time..the home was very spacious and comfortable..great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen P. $662 nightly $748 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/bcfc0861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/1ce3fb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet Mount Snow/Stratton Skiing/hiking [](https://www.expedia.com/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information) East Dover 9.8/10 Exceptional (10 reviews) "Easy to find! Clean! Cozy!! Would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy-michael G. $432 nightly $488 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/c179d1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/7e02a3bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/b3bdf68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496357/8f85f7fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK [](https://www.expedia.com/Jamaica-Hotels-Mountain-Chalet-7min-To-Ski-Stratton-WoodStove.h108496357.Hotel-Information) Jamaica 7.0/10 Good (2 reviews) "Its a cabin. Very fun for a group of friends. I wouldnt bring a family here. No running water in the morning" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hugo T. $240 nightly $271 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Jamaica-Hotels-Mountain-Chalet-7min-To-Ski-Stratton-WoodStove.h108496357.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/eda7773c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/909249f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/f7ab718d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101360000/101355900/101355890/ec10883e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly! [](https://www.expedia.com/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information) Wardsboro 10/10 Exceptional (16 reviews) "We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph R. $402 nightly $454 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Wardsboro-Hotels-Brook-Haven-Retreat-Minutes-To-Mt-Snow-Stratton-Pet-Friendly.h101355890.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/6da0ce7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/62ad9b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/526de6a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113100000/113092300/113092281/d54b3197.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton! [](https://www.expedia.com/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information) Wardsboro 10/10 Exceptional (5 reviews) "Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen T. $502 nightly $567 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Wardsboro-Hotels-The-Mont-Haus-Minutes-To-Mt-Snow-Stratton.h113092281.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/cc65421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/83acf129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/7d6bcc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/aaebfa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private cabin: 7 mins to slopes, wood fireplace [](https://www.expedia.com/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information) Dover 9.8/10 Exceptional (6 reviews) "We spent the week, excellent location and the home was exactly as described in listing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris R. $714 nightly $807 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/West-Dover-Hotels-Private-Cabin-7-Mins-To-Slopes.h105982869.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/f19f2000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/w904h683x60y0-51916776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/31e1efc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82830000/82822100/82822044/c8dd373f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green Mountain Manor - Ski and Summer Chalet [](https://www.expedia.com/Bondville-Hotels-Shuttle-Access-Ski-House.h82822044.Hotel-Information) Winhall 9.8/10 Exceptional (7 reviews) "Beautiful property less than 5 minutes from Stratton!! Very private and secluded" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay T. $4,448 nightly $5,026 total Feb 21 - Feb 22 Total with taxes and fees [](https://www.expedia.com/Bondville-Hotels-Shuttle-Access-Ski-House.h82822044.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/d74e8c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/deccb16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/74c46c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75640000/75637200/75637196/6bb1cc24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres [](https://www.expedia.com/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information) Stratton 10/10 Exceptional (5 reviews) "We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas D. $676 nightly $764 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Stratton-Hotels-HYGGE-HOUSE-Green-Mountain-Chalet-With-Sauna-And-Treehouse.h75637196.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/0d4d95fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/33af9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/w2180h1456x4y0-3d3ff46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/e95e3631.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Private Chalet - 4 mins to Mt Snow [](https://www.expedia.com/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information) Dover 10/10 Exceptional (2 reviews) "Mary and Adam were absolutely lovely hosts! From the initial booking to check-in and throughout our stay, they were incredibly responsive. The house was fantastic—completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldn’t stay longer. Thank you, Mary and Adam, for a wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia N. $579 nightly $655 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1071x0y2-62744863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1076x0y4-eec2a42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1070h1076x5y0-75daf8bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/84b8211e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub! [](https://www.expedia.com/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information) Dover 10/10 Exceptional (7 reviews) "We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris I. $635 nightly $718 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/5f637af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/dcc44385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/38bc7f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/4c3f61c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Charming Chalet with Hot Tub 1 Mile to Mt. Snow [](https://www.expedia.com/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information) Dover 10/10 Exceptional (15 reviews) "This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kaymari T. $852 nightly $963 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/76d2f10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/f158318f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/3a0b064f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/94109ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus [](https://www.expedia.com/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information) Dover 10/10 Exceptional (10 reviews) "Helpful, fun and warm. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony S. $925 nightly $1,045 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/a3e005f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/407a0d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/6a20b4d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/121000000/120430000/120430000/120429915/f3293a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow [](https://www.expedia.com/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.Hotel-Information) Jamaica 10/10 Exceptional (2 reviews) "Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025\. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laird N. $1,108 nightly $1,202 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Jamaica-Hotels-PreLaunch-A-Frame-Hot-Tub-Sauna-EV-Stratton.h120429915.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.com/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22®ionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL) Chalets [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CHALET) Villas [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Vermont%2C+United+States+of+America®ionId=89014&latLong=43.262848%2C-72.595108&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Chalets.d89014-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Chalets.d89014-aaChalets.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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 "Accommodating staff" [](https://expedia.com/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 "excellent " [](https://expedia.com/Bennington-Hotels-The-Palmer-House-Resort.h6028480.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 "Staff very nice and professional. Hotel clean" [](https://expedia.com/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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 "." [](https://expedia.com/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.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 "Clean room! Great food!" [](https://expedia.com/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!" [](https://expedia.com/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![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 "Staff was great! Used the business office which was easily accessible, location is great! " [](https://expedia.com/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Long Trail House at Stratton Mountain Resort](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31db03a1_y.jpg) ### Long Trail House at Stratton Mountain Resort 10/10 Excellent "Nice place and great location!!!" [](https://expedia.com/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information) ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8_y.jpg) ### The Manchester View 10/10 Excellent "The MV was perfect for a getaway to the southern greens for snow. Place was clean, great water pressure, and heat. Had to upgrade my room and it wasn't a problem. Looking forward to coming back. " [](https://expedia.com/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) ## Find out more about Chester ## Chester Chalets information | Number of reviews | 129 | | ----------------- | ----------- | | Accommodation | 102 Chalets | | Lowest Price | $271 | | Highest Price | $5,026 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Chester Depot ](https://www.expedia.com/Chester-Depot-Chester-Hotels.0-n553248635976384383-0.Travel-Guide-Filter-Hotels) - [Hotels near Bonnie's Bundles Dolls ](https://www.expedia.com/Bonnies-Bundles-Dolls-Hotels.0-l553248621561865050-0.Travel-Guide-Filter-Hotels) - [B&B in Andover ](https://www.expedia.com/Andover-Bed-And-Breakfast.d6023580-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Andover ](https://www.expedia.com/Andover-Cabins.d6023580-aaCabins.Travel-Guide-Accommodation) - [Resorts in Andover ](https://www.expedia.com/Andover-Resorts.d6023580-aaResorts.Travel-Guide-Accommodation) - 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