Title: Book the Best ROMANTIC Hotels in Chester, VT from CA $175 - 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 $175 - ![](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 [Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-03&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Jan 4 - Jan 5](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-04&endDate=2026-01-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Chester romantic hotels ![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 | Living area](https://images.trvl-media.com/lodging/2000000/1160000/1155000/1154949/074a9a47.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/ad9a6e84.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) ![Interior](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/286eff53.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/123000000/122980000/122978200/122978111/2f60e9cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Hideaway Inn Mt. Snow [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.Hotel-Information) West Dover 9.4/10 Exceptional (13) "Great cozy hotel very close to Mount Snow. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuhui CA $181 CA $200 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/West-Dover-Hotels-Hideaway-Inn-Mt-Snow.h122978111.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) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/2118745d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/b14a9816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/e38be73f.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 (634) "Scenic balcony. Friendly staff. We had a lovely stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis CA $209 CA $227 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![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) ![View from property](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/2e9ea916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Accessible, Ensuite (Old Solarium Queen)](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/0d6df977.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 (841) "Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaime CA $165 CA $182 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/d5b8706f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/490f03e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/0f2bf37c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970529/bca550da.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 (372) "We loved staying here! It is very quaint, everyone is friendly and the restaurant is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $197 CA $214 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Claremont-Hotels-The-Common-Man-Inn-Restaurant.h2970529.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9cdfa045.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/b043b966.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/4000000/3560000/3555900/3555821/8eb2a3d4.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 (1006) "Very comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $221 CA $239 total includes taxes & fees Jan 8 - Jan 9 [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.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) ![Room 9 | View from room](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/75e32be4.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) ### Colonel Williams Inn [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) Brattleboro 9.8/10 Exceptional (341) "Absolutely stunning bed and breakfast! The room and facilities were clean and welcoming. We really enjoyed the decorations and details of the house. The breakfast was delicious! Will definitely be coming back next time we are in town for ski! Highly recommended staying at Colonel Williams! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ekaterina CA $214 CA $236 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/1d2c94d1.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) ![Sauna, aromatherapy, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/a736e5ee.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 (941) "The suite has everything what we need it ,this place is great for stay ,everyone is so polite ,location is great .Highly recommend!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bozena CA $190 CA $217 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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/1000000/810000/800800/800765/7c69c2ec.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) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a.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 (944) "Place definitely needs some updating but it was clean and the staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline CA $231 CA $280 total includes taxes & fees Jan 14 - Jan 15 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/501f4323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/61c9c6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/978b1784.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 (781) "Clean room, very nice staff, everything was excellent! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $191 CA $231 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.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=2026-01-18&endDate=2026-01-19®ionId=89014&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chester Hotel Reviews ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "They are pros @ hospitality from the front desk to activities. Clean everywhere.Comfortable beds,room,communal & quiet spaces,& a great breakfast & dinner in their cozy restaurant. We had a suite,so a longer stay would have been easy. S'mores around the fire pits was a bonus, as the snow lightly fell. Festival weekend,but will consider adding time for a more relaxed trip & time to read by the scenic views of VT " [](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 "The suite has everything what we need it ,this place is great for stay ,everyone is so polite ,location is great .Highly recommend!!!" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Stayed here twice. Both times were excellent. Dogs are welcomed and they do a great job making your pets feel welcomed as well." [](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.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 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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