Title: Chester B&B: Find the Best Bed and Breakfast from CA $138 | 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 a Bed and Breakfast in Chester from CA $138 - ![](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 prices for these dates Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester B&B ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/f814b3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/327ad7fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/0f0b56c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/ae105a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery Chester 9.2/10 Wonderful (106) "Good breakfast and dinner options. Great location for hiking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $272 CA $297 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/a1626ba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/1377c15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/411cc5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938154/w1536h1021x0y3-8fc8ac6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Room in Historic Inn! 20 Minutes to Okemo! Chester Depot 9.2/10 Wonderful (18) "The Chester Inn was beautiful and located in downtown Chester. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter C. CA $139 CA $234 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chester-Hotels-Room-In-Historic-Inn-20-Minutes-To-Okemo.h83938154.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/c51b349e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/223d62f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/abe9b83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/3195c3db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo! Chester Depot 9.0/10 Wonderful (2) "Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacque CA $125 CA $226 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chester-Hotels-Historic-Chester-Inn-Circa.h102119969.Hotel-Information) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/88000000/87140000/87135800/87135743/f57da4ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87140000/87135800/87135743/97bc445d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/88000000/87140000/87135800/87135743/3e3c4e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87140000/87135800/87135743/580ef989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Honeymoon Suite with Jacuzzi Tub in Historic Inn Chester Depot 8.6/10 Excellent (7) "Charming place, hope to go back soon." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon S. CA $196 CA $305 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chester-Hotels-Honeymoon-Suite-With-Jacuzzi-Tub-In-Historic-Inn.h87135743.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/7656b8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/d309381b.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/84000000/83940000/83938200/83938140/6d1c5ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83940000/83938200/83938140/8d211417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King & Queen Suite in Historic Inn Circa 1780 Chester Depot 9.8/10 Exceptional (16) "Central for our needs. easy check in process. Lovely large room with comfy beds. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HIlary H. CA $391 CA $570 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chester-Hotels-King-Queen-Suite-In-Historic-Inn-Circa-1780.h83938140.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/85d1c6cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c0073409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/4ee226d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/44151c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bromley View Inn Bondville 9.0/10 Wonderful (401) "Overall a decent stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Libin [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1025h684x0y3-22b2c22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Room](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, garden views ](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/f95851fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/730277ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Columns Inn Newfane 9.8/10 Exceptional (12) "Cozy inn in a beautiful setting, and great staff and service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Archith [](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.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) ![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) ![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 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 $197 CA $217 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/df603ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/6c1e93ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Blue Room](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/a33464ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/d8604c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Barn Inn Keene 9.6/10 Exceptional (165) "Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) natalia CA $175 CA $190 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/5f513e0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/6aabd3c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/e0958349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jackson West Woodstock 9.8/10 Exceptional (252) "Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaunita CA $209 CA $230 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/d7baa23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/33fd758e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Double Room, Courtyard View](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/ce0b45d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Double Room, Garden View](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/abaf26b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay At Jimmy's Woodstock 10/10 Exceptional (46) "Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $279 CA $307 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Fireplace, Mountainside](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/e3012ea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/1e06337a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace, Mountainside](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/ca771bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deerfield Valley Inn West Dover 9.6/10 Exceptional (86) "We had a lovely time staying here. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff CA $90 CA $138 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![Mountain view](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/f168cf38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/b590c7bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed | Mountain view](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/60d1e2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cottage | Private kitchen](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/8785d8cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windham Hill Inn West Townshend 8.6/10 Excellent (37) "This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $252 CA $275 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/534fcc92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/cdc27f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/ba818b99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Bass Suite)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/6d7c4545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Manchester Manchester 10/10 Exceptional (280) "Great establishment " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda CA $231 CA $255 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/dda7c041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/430958e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed, Fireplace, Mountain View | Bathroom](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/fb3063fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/4495d308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Ormsby Hill Manchester Center 9.8/10 Exceptional (149) "Lovely place to stay Jack and Maryann excellent hosts" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lenny CA $271 CA $299 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Bennington-Hotels-The-Inn-At-Ormsby-Hill.h6025401.Hotel-Information) ![Economy Room](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/ae1d5a64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/62f98cd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/199515ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/676cb54e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vesper Woodstock 9.2/10 Wonderful (46) "Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roger CA $218 CA $240 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/cc8097e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/fa801882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/487ff1a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big Bears Lodge West Dover 9.0/10 Wonderful (185) "The owners were wonderful: kind, interesting to talk to, and very hospitable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $234 CA $257 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/34f36e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/4c68c022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/114ee15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (The Brighton Room)](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/abe8f80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The One Cat B&B Brattleboro 9.6/10 Exceptional (78) "Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cara CA $351 CA $386 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Brattleboro-Hotels-The-One-Cat-BB.h13578971.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/59f5ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun and Moon Room](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/40986f17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/16188707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on Putney Road Brattleboro 9.8/10 Exceptional (56) "wonderful atmosphere, great breakfast, friedly staff, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt CA $374 CA $412 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/a23bd7ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Regional cuisine](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/68993b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, minibar, desk](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/d4a96b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Regional cuisine](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/cea1ec7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesterfield Inn West Chesterfield 9.0/10 Wonderful (104) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne CA $422 CA $458 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.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=2025-12-12&endDate=2025-12-13®ionId=89014&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_89014) ![](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-Bed-And-Breakfast.d89014-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Bed-And-Breakfast.d89014-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/6f88107a_y.jpg) ### Aspen At Manchester 10/10 Excellent "Great location Everything updated Pleasant greeting in lobby" [](https://expedia.ca/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information) ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "Staff was accommodating. Got a Free upgrade to my room" [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.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 "good" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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 "It was great. The room was wonderful and the staff great." [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Clean good service and location " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.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) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n go off for the day. All was very nice. Thank you!" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.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 "Hands down one of the best places I have ever stayed. Beautiful view, great room and very cozy no matter where you were in the inn." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Mountaineer Inn](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d_y.jpg) ### Mountaineer Inn 10/10 Excellent "Small but clean room. Hotel is under construction but staff was accommodating and pleasant to work with durning our travel. If traveling for work we’d stay again " [](https://expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 2,264 | | --- | --- | | Accommodation | 52 B&B | | Lowest Price | CA $138 | | Highest Price | CA $570 | ## Frequently asked questions ### Searching for B&Bs in Chester? > If you're looking for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie's Bundles Dolls are worth a stop. ### Are you thinking about B&Bs over traditional hotel rooms? > With attentive service, opportunities to mingle with other guests, and hearty breakfasts, B&Bs provide a unique setting. ### What are the top B&Bs in Chester? > You might be interested in one of these choices if you're hoping to find a place to stay where breakfast is included with your stay: [Fullerton Inn](https://www.expedia.ca/Chester-Hotels-Fullerton-Inn.h15845368.Hotel-Information)[Stone Hearth Inn and Eatery](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information)[Motel in the Meadow](https://www.expedia.ca/Chester-Hotels-Motel-In-The-Meadow.h14724639.Hotel-Information) ### How many Bed & Breakfasts should I expect to find in Chester? > Expedia has 5 B&Bs for your stay in Chester. ### What's the best time of year to stay at a B&B in Chester? > When you're dreaming of a escape to Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall. ### What is there to do in Chester? > If you like to experience a new place through your taste buds, you'll be sure to enjoy Chester for its coffeehouses and restaurants. If you're looking to find something to do during your travels, you might consider checking out DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites like Stratton Mountain Resort or Grafton Historical Society if you have time to see more of the area. ### How can I get to and around Chester? > You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away from the city center. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. 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