Title: Book the Best ROMANTIC Hotels in Chester, VT from CA $187 - Chester Romantic Getaways | 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 Romantic Hotels in Chester, VT from CA $187 - ![](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 Romantic Hotels Tonight [Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Chester romantic hotels ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/67f64adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/a0514206_edited_9a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/286eff53.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 (3) "Really happy with our stay and the way we felt at this hideaway " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edwin CA $215 CA $237 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/bb7b6824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/aa061d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Garden View](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/4f6e289d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Spa Bath](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/8a170d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Weathersfield [](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information) Perkinsville 9.8/10 Exceptional (70) "The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua [](https://www.expedia.ca/Perkinsville-Hotels-The-Inn-At-Weathersfield.h1154949.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Theatre show](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/afa5570f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hiking](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/501b3c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Latchis Hotel [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) Brattleboro 8.4/10 Very good (837) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $173 CA $191 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Sauna, aromatherapy, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5.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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/1d2c94d1.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 (927) "Great place to stay while skiing at okemo" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken CA $218 CA $249 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/eba3c737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/b17a8caf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/ad2eea38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Hotel, an Ascend Collection Hotel [](https://www.expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) West Chesterfield 9.6/10 Exceptional (629) "Clean room, beautiful location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcie CA $222 CA $240 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Pub](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9384b42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/2a21d8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/cd3048ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/30a7f959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Keene Downtown [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) Keene 8.8/10 Excellent (1003) "Very comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $248 CA $269 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/c3df1806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/4e3f46ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/3d6e59aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Bear Lodge at Stratton Mountain Resort [](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) Stratton 7.6/10 Good (941) "We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark CA $221 CA $268 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/27e1cc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/9331b839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG [](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) Brownsville 9.0/10 Wonderful (779) "Clean room, very nice staff, everything was excellent! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $177 CA $216 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/81dd974d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/7fbb1dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/4bee0dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonel Williams Inn [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) Brattleboro 9.8/10 Exceptional (340) "Very nice historic inn. We enjoyed our stay. Breakfast was exceptional." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) scott CA $195 CA $215 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/38514471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/a0becfcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Designer toiletries, hair dryer, towels, soap](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/654218e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/4a7ed1f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Common Man Inn & Restaurant [](https://www.expedia.ca/Claremont-Hotels-The-Common-Man-Inn-Restaurant.h2970529.Hotel-Information) Claremont 9.6/10 Exceptional (370) "Great place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Candace M CA $172 CA $187 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Claremont-Hotels-The-Common-Man-Inn-Restaurant.h2970529.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=2026-01-01&endDate=2026-01-02®ionId=89014&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![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 "Experience was flawless from Check-In to Checking Out 👌🥰 The Staff was absolutely delightful - attentive , professional, so helpful and the Grouse Staff was equally outstanding - Bartender, and special mention for Chef Jeffery, and Servers Aria and Bean. We definitely plan to stay here again on our next visit to Manchester 👌❣️" [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Clean rooms, front desk personal could use people skill update, not young lady there this am, she was great. Guys in restaurant were the best. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.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 "Yea" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG 10/10 Excellent "Clean room, very nice staff, everything was excellent! " [](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Complimentary breakfast was nice. Room was clean. " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![The 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 "Courteous staff Clean room" [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.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, clean room in prime location" [](https://expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Chester? ### What's the best place to stay for a romantic getaway to Chester? ### When is the best time of year for a romantic getaway to Chester? ### What is there to do in Chester? ### What's the best way to get to Chester and around town during my romantic getaway? ## Explore a world of travel with Expedia - 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