Title: Chester B&B: Find the Best Bed and Breakfast from CA $182 | 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [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) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester bed & breakfast ![Front of property](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1.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) ![Porch](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/450d23d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, Mountain View](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/48815e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stone Hearth Inn and Eatery [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.Hotel-Information) Chester 9.2/10 Wonderful (109 reviews) "So great all around!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet CA $368 CA $402 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.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) ![Interior entrance](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/44151c50.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) ### Bromley View Inn [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) Bondville 9.0/10 Wonderful (411 reviews) "Really cute simple clean ski lodge everything that you need and a great breakfast in the morning!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nichole [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.Hotel-Information) ![Land view from property](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1023h453x0y0-571ad601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/ea836d50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, garden views ](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/24332bc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/w1025h684x0y3-22b2c22c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Columns Inn [](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) Newfane 9.6/10 Exceptional (19 reviews) "Everything was great 👍 I will stay there again and highly recommend to others " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda [](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/1e0ac20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/0ee737a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![River View](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/3b283cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/096e29dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harvest Barn Inn [](https://www.expedia.ca/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.Hotel-Information) Bellows Falls 9.8/10 Exceptional (245 reviews) "Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) RICHARD [](https://www.expedia.ca/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.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) ![Lounge](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/d8604c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/a625cff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/f54cc2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Carriage Barn Inn [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.Hotel-Information) Keene 9.6/10 Exceptional (167 reviews) "Very helpful and welcoming host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce CA $175 CA $190 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.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 4](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/22815dbf.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 (342 reviews) "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 $204 CA $225 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/b6d65569.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) ![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) ### The One Cat B&B [](https://www.expedia.ca/Brattleboro-Hotels-The-One-Cat-BB.h13578971.Hotel-Information) Brattleboro 9.6/10 Exceptional (78 reviews) "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 $174 CA $192 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Brattleboro-Hotels-The-One-Cat-BB.h13578971.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) ![Classic Room (Cinnamon)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/e69208e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Green Briar) | Living area](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/45cd95f5.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) ### The Inn at Manchester [](https://www.expedia.ca/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information) Manchester Village Historic District 10/10 Exceptional (284 reviews) "super cute and clean, felt like home after not living there for 4 years!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MacLean CA $229 CA $252 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Bennington-Hotels-The-Inn-At-Manchester.h1505817.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/8cc0d819.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) ![Exterior](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/639c20cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deerfield Valley Inn [](https://www.expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) West Dover 9.6/10 Exceptional (95 reviews) "Staff was great and the location is very close to the ski area. Cozy atmosphere at hotel." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Shane [](https://www.expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![Kayaking](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/a19c8d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/ff2febb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/19942074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/e4ab8f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Gentian Lodge at Magic Mountain [](https://www.expedia.ca/Londonderry-Hotels-Blue-Gentian-Lodge-At-Magic-Mountain.h14586320.Hotel-Information) Londonderry 9.2/10 Wonderful (113 reviews) "Lovely pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $231 CA $255 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Londonderry-Hotels-Blue-Gentian-Lodge-At-Magic-Mountain.h14586320.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) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/452e126e.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 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) Brattleboro 9.8/10 Exceptional (56 reviews) "wonderful atmosphere, great breakfast, friedly staff, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt CA $326 CA $358 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) ![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) ![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) ![Room, Private Bathroom (Library)](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/60580202.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) ### The Inn at Ormsby Hill [](https://www.expedia.ca/Bennington-Hotels-The-Inn-At-Ormsby-Hill.h6025401.Hotel-Information) Manchester Center 9.8/10 Exceptional (151 reviews) "Lovely place to stay Jack and Maryann excellent hosts" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lenny CA $304 CA $334 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Bennington-Hotels-The-Inn-At-Ormsby-Hill.h6025401.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) ![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/104000000/103190000/103188700/103188664/5423776f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite, Garden View](https://images.trvl-media.com/lodging/104000000/103190000/103188700/103188664/4c69dfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay At Jimmy's [](https://www.expedia.ca/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information) Woodstock 10/10 Exceptional (46 reviews) "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 $346 CA $380 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Woodstock-Hotels-Stay-At-Jimmys.h103188664.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/0ba93825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/2970ae6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/2533d22f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/104000000/103420000/103415500/103415437/589572bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Vesper [](https://www.expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) Woodstock 9.2/10 Wonderful (52 reviews) "Charming bed and breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $224 CA $247 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Woodstock-Hotels-The-Vesper.h103415437.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/b9dbfee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/9a1e2ed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Jackson [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) West Woodstock 9.8/10 Exceptional (261 reviews) "The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby [](https://www.expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ![Room, 1 Queen Bed, Garden View | Mountain view](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/ee964e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/26455a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cottage | Private kitchen](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/159c71cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/b3c06bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windham Hill Inn [](https://www.expedia.ca/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.Hotel-Information) West Townshend 8.4/10 Very good (38 reviews) "Did not use" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Douglas CA $247 CA $270 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/West-Townshend-Hotels-Windham-Hill-Resort.h94650035.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) ![Property entrance](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/44de1d55.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) ![Restaurant](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/cc8097e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Big Bears Lodge [](https://www.expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) West Dover 9.0/10 Wonderful (186 reviews) "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 $247 CA $272 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576447/b375d11a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576447/7be8391b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576447/1d8a3c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113580000/113576500/113576447/a6423b70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Room 7 - family room sleeps 4 [](https://www.expedia.ca/Manchester-Center-Hotels-Room-7-Family-Room-Sleeps-4.h113576447.Hotel-Information) Manchester 10/10 Exceptional (1 review) "Nice spot, good location. Towels could be better, but overall a great spot. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kuan-Chung CA $102 CA $182 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Manchester-Center-Hotels-Room-7-Family-Room-Sleeps-4.h113576447.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/7179648d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Whirlpool Fireplace Room with Private Deck](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/f1ce012c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/2000000/1580000/1576100/1576027/3339dfd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesterfield Inn [](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information) West Chesterfield 9.0/10 Wonderful (104 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne CA $427 CA $463 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/b1b23979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Suite | Interior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/85691467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/4d2bc29e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/53db29c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deer Brook Inn [](https://www.expedia.ca/Woodstock-Hotels-Deer-Brook-Inn.h122648718.Hotel-Information) Woodstock CA $378 CA $416 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Woodstock-Hotels-Deer-Brook-Inn.h122648718.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=2026-01-27&endDate=2026-01-28®ionId=89014&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&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-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 ![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, nice pool and hot tub, and good price!" [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Every thing was excellent " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.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 "Nicely appointed hotel in the heart of Manchester Center. Walking distance to Northshire Bookstore, shops, restaurants and a supermarket. Pool and hot tub are highlights. " [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.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 place is great. Especially the wood burning stove in the room." [](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) ![The Jackson ](https://images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "Beautiful, quiet inn. We stayed Saturday through Tuesday after the holidyas, so it was especially quiet, just what we wanted. Staff was incredibly attentive and engaging, rooms were unique and comfortable. I highly recommend The Jackson. We will be returning in the spring to see the grounds!" [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.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 "Great staff" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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 "Very convenient location.! Spacious and clean room. " [](https://expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.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 "Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! " [](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 "Wonderful stay at this beautiful inn. Couldn’t fault it. The only downside is that the bar and restaurant isn’t open every evening. When it was open, it was excellent - top quality food and brilliant staff." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 2,641 | | ----------------- | ------- | | Accommodation | 62 B&B | | Lowest Price | CA $182 | | Highest Price | CA $463 | ## Frequently asked questions ### Searching for B&Bs in Chester? ### Are you thinking about B&Bs over traditional hotel rooms? ### What are the top B&Bs in Chester? ### How many Bed & Breakfasts should I expect to find in Chester? ### What's the best time of year to stay at a B&B in Chester? ### What is there to do in Chester? ### How can I get to and around Chester? ## 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) - [Chalets in Andover ](https://www.expedia.ca/Andover-Chalets.d6023580-aaChalets.Travel-Guide-Accommodation) - [Country Houses in Andover ](https://www.expedia.ca/Andover-Country-House.d6023580-aaCountryHouse.Travel-Guide-Accommodation) - 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