Title: Chester Vacation Home Rentals from CA $233: Search Top Private Vacation Homes for Rent | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Chester Vacation Rentals ![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 prices for these dates In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/8f3740a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, in-room safe, desk, WiFi](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/w1351h902x5y0-ea88849f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/d60449fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105340000/105335900/105335886/98b36931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### WhiSki Cabin - 12 Acres With a Mountain View! Chester 10/10 Exceptional (3) "We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. " CA $752 CA $1,405 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chester-Hotels-WhiSki-Cabin-12-Acres-With-A-Mountain-View.h105335886.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119350000/119345400/119345369/344bf597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119350000/119345400/119345369/50226a67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119350000/119345400/119345369/5cc4c967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119350000/119345400/119345369/3516607a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil farmhouse in Manchester - perfect for ski or summer fun! Manchester CA $469 CA $966 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Manchester-Center-Hotels-Tranquil-Farmhouse-In-Manchester-Perfect-For-Ski-Or-Summer-Fun.h119345369.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/4e6773ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/cf58af9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/0d26f53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87140000/87136000/87135975/1f2d7230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Whimsical Room & Private Bathroom in Historic Inn Chester Depot 8.8/10 Excellent (9) "After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!" CA $138 CA $233 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Whimsical-Room-Private-Bathroom-In-Historic-Inn.h87135975.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/9fc41d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/578d98e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/fb8c05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101480000/101473400/101473310/dffaa55c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester Farmhouse Ski Retreat near Slopes Chester Depot 9.6/10 Exceptional (15) "Great cozy home for our trip to Vermont. Very comfortable. Recommend walking over to country girl dinner and the Scottish pub." CA $264 CA $558 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Chester-Hotels-Charming-Chester-Farmhouse-Peaceful-And-Close-To-Everything.h101473310.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/cdd47fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/f081e4c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/440e40cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, toilet paper](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/00b27946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom condo in delightful Dover Dover 9.0/10 Wonderful (4) "Condo was perfect for our stay. Very quiet area despite being near Mt Snow and Wilmington area. Great bakery close by for wonderful morning pastries. Updated/renovated condo. Loved our time there. Owners response to an issue we had (our personal issue) was greatly appreciated. Would stay again!!!!" CA $149 CA $282 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/West-Dover-Hotels-Charming-1-Bedroom-Condo-In-Delightful-Dover.h115660983.Hotel-Information) ![Smart TV, fireplace, table tennis](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/f5e61b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/3902b9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/ab4d2539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101090000/101085500/101085488/d6227626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table. Dover 10/10 Exceptional (5) "Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. " CA $162 CA $607 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/West-Dover-Hotels-Fantastic-Location-Mt-Snow-Ski-Off.h101085488.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/620d544b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, internet, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/5f732777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/cc74d03c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/45000000/44580000/44577300/44577227/d295676b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts Stratton 7.8/10 Good (52) "Location was great, pool, hot tubs and sauna were great" CA $141 CA $390 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Stratton-Hotels-Stratton-Mountain-Condo-With-Shared-Pool.h44577227.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) ![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/3315ad26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/48ea3a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Friendly Hilltop House In Putney Vermont Putney 9.4/10 Exceptional (56) "The property was beautiful--great views, super peaceful, and fabulous hosts. " CA $170 CA $348 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/9e5ceac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/ed1ab9f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/6b0e5b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/101000000/100540000/100538400/100538389/367a6860.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake Front Family Friendly Escape Newport 10/10 Exceptional (4) "Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!" CA $201 CA $545 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Newport-Hotels-Lake-Front-Family-Friendly-Escape.h100538389.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113740000/113731900/113731870/db562d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113740000/113731900/113731870/7b7b4e33_edited_e97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/114000000/113740000/113731900/113731870/w1559h1136x4y0-0c75dbba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113740000/113731900/113731870/484e21ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton & Mountain Snow/ 3-bedroom bungalow/Hot Tub/Sauna/Pave Driveway Wardsboro 9.6/10 Exceptional (4) "Thank you :) lovely home :) I truly enjoy the paved driveway :was clear I was able to go in and out of Mountain Snow & Stratton ski Mountain.Immaculate clean house" CA $251 CA $1,063 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Wardsboro-Hotels-Stratton-Mountain-Snow-3-Bedroom-BungalowHot-TubSaunaPave-Driveway.h113731870.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/ae0971bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/f38617c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/bf6afd61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117920000/117913300/117913271/8d9f525d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Home Walk to Downtown! Keene 10/10 Exceptional (1) "Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even... CA $442 CA $1,025 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Keene-Hotels-The-Leverett-House-In-Charming-Keene.h117913271.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/8d25e78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/96ddc65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/9d2d9170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101900000/101895700/101895664/ac990b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carol - 10 minutes to Okemo & Newly Renovated Cavendish 10/10 Exceptional (6) "Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again" CA $220 CA $415 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Cavendish-Hotels-The-Carol-Styled-And-Freshly-Renovated-Stay10-Minutes-To-Okemo.h101895664.Hotel-Information) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/7571a0ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/29b5b165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/eeebd729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/107000000/106680000/106675000/106674947/ee72a250.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Enjoy this authentic and cozy VT Barn with Brand New Hot Tub Londonderry CA $354 CA $700 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Londonderry-Hotels-Enjoy-This-Authentic-And-Cozy-VT-Barn-With-Brand-New-Hot-Tub.h106674947.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109050000/109040400/109040351/4c5da9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/110000000/109050000/109040400/109040351/72083d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109050000/109040400/109040351/3ed88ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109050000/109040400/109040351/5fc90b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Killington Vistas 92: 4-Bedroom Luxury Ski On Ski Off Home w/ Hot Tub, Mountain Views. Killington CA $935 CA $2,069 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Killington-Hotels-Killington-Vistas-92-4-Bedroom-Luxury-Ski-On-Ski-Off-Home-W-Hot-Tub.h109040351.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/02e05ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/a42c90fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/91a11f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/4f52e53a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski in Ski out Condo! Pool access Stratton 9.0/10 Wonderful (2) "Great location with plenty of space for the whole family. Highly recommend!" CA $237 CA $735 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Stratton-Hotels-Ski-In-Ski-Out-Condo-Pool-Access.h94786075.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/074f8953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/e4ca34c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/ef58d29c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, WiFi](https://images.trvl-media.com/lodging/111000000/110220000/110215300/110215244/e5b1b5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes. Bridgewater 8.0/10 Very good (2) "Great place for a ski weekend" [](https://www.expedia.ca/Bridgewater-Corners-Hotels-Cozy-Vermont-House-Near-Killington-And-Woodstock-Discounted-Lift-Tickets.h110215244.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/120000000/119540000/119535800/119535742/c5a30b0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119540000/119535800/119535742/8d6b43fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/120000000/119540000/119535800/119535742/b0959a32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119540000/119535800/119535742/04b7cf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MUST-SEE VERMONT MAGICAL FALL FOLIAGE SEASON BOOK NOW Springfield CA $203 CA $523 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Springfield-Hotels-MUST-SEE-VERMONT-MAGICAL-FALL-FOLIAGE-SEASON-BOOK-NOW.h119535742.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107280000/107272100/107272080/91628d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107280000/107272100/107272080/7cc21470.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107280000/107272100/107272080/3fd264e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107280000/107272100/107272080/7cf48072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8mins Mount Snow - NEW Cabin 3600SF - Game Room - 20%OFF Wardsboro CA $1,614 CA $2,534 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/West-Wardsboro-Hotels-Bearmont-A-New-Modern-Rustic-Cabin-Sleeps-12.h107272080.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/0a51ad2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/f922de49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/17915502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books, offices](https://images.trvl-media.com/lodging/79000000/78350000/78342500/78342432/c88e2df0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit Bridgewater 9.4/10 Exceptional (16) "Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect " CA $191 CA $691 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bridgewater-Corners-Hotels-NEW-Blueberry-Hill-Escape-Pet-Friendly-King-Bed-Fire-Pit-Grill.h78342432.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/7d6a1254.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/0226cb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/314d0c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/120000000/119100000/119097900/119097866/bf925c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MtSnow\* HotTub\* Pool \* AirHockey\*PingPong \* Darts Wilmington CA $256 CA $852 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Wilmington-Hotels-MtSnow-HotTub-Pool-AirHockeyPingPong-Darts.h119097866.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=2025-10-20&endDate=2025-10-21®ionId=89014&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d89014-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Private-Vacation-Homes.d89014-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "We checked in and it went great. The staff was very friendly and accommodating at the front desk. We went to the restaurant for dinner around seven and were unable to be seated being told. It would be 835, we were good with that and waited at the bar. We never received a call. We followed up a couple of times with the hostess and ultimately ordered takeout from the bar.… jimmy at the bar was very helpful in getting our order in and out to us before the kitchen closed, which was in less than 10 minutes . We got we got to the room and first appearance It looked great until we retired for the night and the are bedding still had stain from previous use. Ultimately there has been some great and some really not so great experience – we’ll see what tomorrow brings.. " [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![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) ![Mountaineer Inn](//images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d_y.jpg) ### Mountaineer Inn 10/10 Excellent "The property was well kept and was close to different trails and beautiful views. We felt safe and comfortable. We want to come back in the winter to stay again! " [](https://expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.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) ## Find out more about Chester ## Chester Vacation Homes information | Number of reviews | 137 | | --- | --- | | Accommodation | 1137 Vacation Homes | | Lowest Price | CA $233 | | Highest Price | CA $2,534 | ## 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) - 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