Title: Jamaica B&B: Find the Best Bed and Breakfast from CA $143 | Expedia.ca [Hotels in Jamaica](https://expedia.ca/Jamaica-Hotels.d184052.Travel-Guide-Hotels)[Vacation Rentals in Jamaica](https://expedia.ca/Jamaica-Vacation-Rentals.d184052.Travel-Guide-VacationRentals)[Flights to Jamaica](https://expedia.ca/Cheap-Flights-To-Jamaica.d184052.Travel-Guide-Flights)[Jamaica Car Rentals](https://expedia.ca/Car-Rentals-In-Jamaica.d184052.Car-Rental-Guide)[Jamaica Vacation Packages](https://expedia.ca/Jamaica.d184052.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/5e96b8e74a3fe03dd3d1f81bf3b2ae7e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Jamaica from CA $143 ![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 Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=184052&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Jamaica B&B ![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) ![Carriage House C](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/8a063a5b.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) ### Colonel Williams Inn Brattleboro 9.8/10 Exceptional (329) "Very nice historic inn. We enjoyed our stay. Breakfast was exceptional." CA $202 CA $223 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/a1028674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/df98e0be.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) ![Exclusive Room | Living area](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/7573dd00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Columns Inn Newfane 9.2/10 Wonderful (5) "So much charm! This place was absolutely outstanding. Already trying to figure out how we can come back for a longer stay." CA $230 CA $251 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.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) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1510000/1503000/1502963/c28fd1d0.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 Bondville 9.2/10 Wonderful (389) "Older ski mountain motel, kind of a homey feeling. Our stay was very quiet and comfortable. Would stay again" CA $130 CA $143 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-Bromley-View-Inn.h1502963.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) ![Property grounds](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/77acac6d.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) ![Interior](https://images.trvl-media.com/lodging/18000000/17290000/17287000/17286987/6a7db77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harvest Barn Inn Bellows Falls 9.8/10 Exceptional (237) "Breakfast was amazing! Hosts were super friendly and we are looking forward to returning there again! " CA $184 CA $201 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bellows-Falls-Hotels-Harvest-Barn-Inn.h17286987.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) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/c09bb59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/ac7a6ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/dd07686d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Gentian Lodge at Magic Mountain Londonderry 9.2/10 Wonderful (110) "Lovely pleasant stay. " CA $240 CA $265 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Londonderry-Hotels-Blue-Gentian-Lodge-At-Magic-Mountain.h14586320.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/38ec3c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/fdd13f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/a963d997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/97e6f6a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Engel House Jacksonville 9.4/10 Exceptional (13) "The perfect Vermont Bed and Breakfast. " CA $242 CA $264 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Jacksonville-Hotels-The-Engel-House.h67598596.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/b590c7bd.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 8.4/10 Very good (36) "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. " CA $253 CA $276 total includes taxes & fees Oct 21 - Oct 22 [](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) ![Suite (Silver Birch)](https://images.trvl-media.com/lodging/2000000/1510000/1505900/1505817/6b885960.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) ![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) ### The Inn at Manchester Manchester 10/10 Exceptional (265) "Friendly staff and very nice breakfast. " CA $207 CA $228 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Interior detail](https://images.trvl-media.com/lodging/7000000/6030000/6025500/6025401/4495d308.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) ![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) ### The Inn at Ormsby Hill Manchester Center 9.8/10 Exceptional (140) "Lovely place to stay Jack and Maryann excellent hosts" CA $250 CA $275 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bennington-Hotels-The-Inn-At-Ormsby-Hill.h6025401.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/dfd331b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/ec7f96e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/4aef8677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/11b23fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wilmington Inn Wilmington 10/10 Exceptional (185) "Breakfast great, staff accommodating, Charlie and crew, made you feel like going to grandmas!" CA $287 CA $326 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Wilmington-Hotels-The-Wilmington-Inn.h3532068.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/5214ab64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/fca3b093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed (Second Floor - Room 8)](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/45f9eb24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/b82005ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Nutmeg Wilmington 9.4/10 Exceptional (403) "Room was clean bathroom was modern large clean staff friendly breakfast was awesome gave you 4 choices cofee and tea all day heated pool in season several rooms to just sit and relax in." CA $216 CA $238 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Wilmington-Hotels-The-Nutmeg.h1482719.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) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/5baffb47.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) ### Inn on Putney Road Brattleboro 9.8/10 Exceptional (55) "Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries." CA $372 CA $409 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.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 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) ![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) ### Deerfield Valley Inn West Dover 9.6/10 Exceptional (69) "We had a lovely time staying here. " CA $146 CA $200 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.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 (181) "So close to Mount snow it’s a great place to stay " CA $233 CA $256 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.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) ![1 bedroom, premium bedding, pillowtop beds, minibar](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/2000000/1580000/1576100/1576027/68993b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Chesterfield Inn West Chesterfield 9.0/10 Wonderful (104) "Great stay" CA $420 CA $456 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information) ![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) ![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) ![Deluxe Room, 1 Queen Bed, Garden View](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/20cd6ab1.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) ### Stone Hearth Inn and Eatery Chester 9.2/10 Wonderful (96) "Sweet place to stay" CA $389 CA $425 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Chester-Hotels-Stone-Hearth-Inn-And-Eatery.h87486236.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) ![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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/114ee15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The One Cat B&B Brattleboro 9.6/10 Exceptional (77) "Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!" CA $338 CA $372 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Brattleboro-Hotels-The-One-Cat-BB.h13578971.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/2544c235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Dorset)](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/4eb135c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage (Farm House) | Private kitchen](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/30a5bc87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502179/6eee3d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hill Farm Inn Arlington 9.6/10 Exceptional (168) "Beautiful location, friendly staff, delicious breakfast and excellent accommodation." CA $325 CA $668 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bennington-Hotels-Hill-Farm-Inn.h1502179.Hotel-Information) ![Standard Room, 1 King Bed, Mountain View | Mountain view](https://images.trvl-media.com/lodging/7000000/6400000/6393200/6393104/318e8076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6400000/6393200/6393104/733025cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6400000/6393200/6393104/fd1f4f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/7000000/6400000/6393200/6393104/21e5c2ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Shire Lodge Manchester Center 9.4/10 Exceptional (153) "Loved our stay at North Shire Lodge.." CA $303 CA $333 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Bennington-Hotels-North-Shire-Lodge-Mountain-View-Pub.h6393104.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) ![Living area](https://images.trvl-media.com/lodging/103000000/102120000/102120000/102119969/2e170eb4.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) ![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) ### 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. " CA $124 CA $225 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chester-Hotels-Historic-Chester-Inn-Circa.h102119969.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=2025-10-21&endDate=2025-10-22®ionId=184052&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%2FJamaica-Bed-And-Breakfast.d184052-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FJamaica-Bed-And-Breakfast.d184052-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Jamaica Hotel Reviews ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Gorgeous suite, staff was so nice and helpful. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.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 "Excellent staff" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.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 "Very courteous staff" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Palmer House Resort, an Ascend Collection Hotel](//images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/b3cf5e7e_y.jpg) ### The Palmer House Resort, an Ascend Collection Hotel 10/10 Excellent "Good time" [](https://expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](//images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "Clean room" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Mountaineer Inn](//images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/7d61f01d_y.jpg) ### Mountaineer Inn 10/10 Excellent "Clean room and spacious. Walkable areas around to explore. Would stay again. " [](https://expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.Hotel-Information) ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Staff was very helpful " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Travelodge by Wyndham Brattleboro VT](//images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/19b6c01d_y.jpg) ### Travelodge by Wyndham Brattleboro VT 6/10 Okay "For the money during peep season it was ok. Otherwise it’s a low quality stay" [](https://expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) ![The Covered Bridge Inn](//images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "We were initially put off by the look of the outside of this “Inn”! But it turns out we were greeted by a smiling and polite person during check in. The room was large, clean, and comfortable. The bathroom had thick towels and well stocked. All and all it was a very pleasant stay at a very reasonable price!" [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ## Find out more about Jamaica ## Jamaica B&B information | Number of reviews | 2,987 | | --- | --- | | Accommodation | 45 B&B | | Lowest Price | CA $143 | | Highest Price | CA $668 | ## Frequently asked questions ### What is the nightly rate for a B&B in Jamaica? > Prices for B&Bs in Jamaica often vary, but you can find a great deal from CA $143 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Jamaica B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high. ### What is the difference between a Jamaica Bed & Breakfast and a hotel? > Every Jamaica B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Jamaica B&Bs. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Londonderry](https://www.expedia.ca/4Star-Londonderry-Hotels.s40-0-d127228.Travel-Guide-Filter-Hotels) - [4 Star Hotels in South Londonderry](https://www.expedia.ca/4Star-South-Londonderry-Hotels.s40-0-d184074.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Stratton](https://www.expedia.ca/5Star-Stratton-Hotels.s50-0-d163002.Travel-Guide-Filter-Hotels) - [B&B in Bondville](https://www.expedia.ca/Bondville-Bed-And-Breakfast.d6049474-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Bondville](https://www.expedia.ca/Bondville-Guest-Houses.d6049474-aaGuestHouses.Travel-Guide-Accommodation) - [Luxury Hotels in Bondville](https://www.expedia.ca/Bondville-Hotels-Luxury-Hotel.0-0-d6049474-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in Bondville](https://www.expedia.ca/Bondville-Hotels-Shopping-Hotel.0-0-d6049474-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Bondville](https://www.expedia.ca/Bondville-Hotels-Spa-Hotel.0-0-d6049474-tSpaHotel.Travel-Guide-Filter-Hotels) - [Bondville Hotels](https://www.expedia.ca/Bondville-Hotels.d6049474.Travel-Guide-Hotels) - [Rv Parks in Bondville](https://www.expedia.ca/Bondville-RV-Parks.d6049474-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Bondville](https://www.expedia.ca/Bondville-Resort-Hotels.d6049474-aaResortHotels.Travel-Guide-Accommodation) - [Vail Resorts in East Jamaica](https://www.expedia.ca/East-Jamaica-Hotels-Vail-Resorts.0-0-d553248635976384572--bVailResorts.Travel-Guide-Filter-Hotels) - [East Jamaica Hotels](https://www.expedia.ca/East-Jamaica-Hotels.d553248635976384572.Travel-Guide-Hotels) - [Resorts in East Jamaica](https://www.expedia.ca/East-Jamaica-Resort-Hotels.d553248635976384572-aaResortHotels.Travel-Guide-Accommodation) - [Adults Only Resorts & in Forest Farms](https://www.expedia.ca/Forest-Farms-Bondville-Hotels-Adults-Only-Resorts.0-n553248635976471678-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Hotels near Jamaica State Park](https://www.expedia.ca/Jamaica-State-Park-Hotels.0-l553248621532666874-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Londonderry](https://www.expedia.ca/Londonderry-Cabins.d127228-aaCabins.Travel-Guide-Accommodation) - [Historic Hotels in Londonderry](https://www.expedia.ca/Londonderry-Hotels-Historic-Hotel.0-0-d127228-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Londonderry](https://www.expedia.ca/Londonderry-Hotels-Hotels-With-Indoor-Pool.0-0-d127228-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Londonderry](https://www.expedia.ca/Londonderry-Hotels-Hotels-With-Kitchenettes.0-0-d127228-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Spa Hotels in Londonderry](https://www.expedia.ca/Londonderry-Hotels-Spa-Hotel.0-0-d127228-tSpaHotel.Travel-Guide-Filter-Hotels) - [Londonderry Hotels](https://www.expedia.ca/Londonderry-Hotels.d127228.Travel-Guide-Hotels) - [Hotels near Magic Mountain Ski Resort](https://www.expedia.ca/Magic-Mountain-Ski-Resort-Hotels.0-l6115886-0.Travel-Guide-Filter-Hotels) - [Hotels near Margie's Muse Handweaving & Gallery](https://www.expedia.ca/Margies-Muse-Handweaving-Gallery-Hotels.0-l553248621532666871-0.Travel-Guide-Filter-Hotels) - [Spa Hotels in Mountain Acres](https://www.expedia.ca/Mountain-Acres-Jamaica-Hotels-Spa-Hotel.0-n553248635976471490-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Mountain Acres](https://www.expedia.ca/Mountain-Acres-Jamaica-Hotels-Wedding-Hotels.0-n553248635976471490-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Mountain Acres Hotels](https://www.expedia.ca/Mountain-Acres-Jamaica-Hotels.0-n553248635976471490-0.Travel-Guide-Filter-Hotels) - [Rawsonville Hotels](https://www.expedia.ca/Rawsonville-Hotels.d553248635976388770.Travel-Guide-Hotels) - [B&B in South Londonderry](https://www.expedia.ca/South-Londonderry-Bed-And-Breakfast.d184074-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hostels in South Londonderry](https://www.expedia.ca/South-Londonderry-Hostels.d184074-aaHostels.Travel-Guide-Accommodation) - [Cheap Hotels in South Londonderry](https://www.expedia.ca/South-Londonderry-Hotels-Cheap-Hotels.0-0-d184074-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in South Londonderry](https://www.expedia.ca/South-Londonderry-Hotels-Luxury-Hotel.0-0-d184074-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [South Londonderry Hotels](https://www.expedia.ca/South-Londonderry-Hotels.d184074.Travel-Guide-Hotels) - [Farmstay in Stratton](https://www.expedia.ca/Stratton-Agritourism.d163002-aaAgritourism.Travel-Guide-Accommodation) - [Apartments in Stratton](https://www.expedia.ca/Stratton-Apartments.d163002-aaApartments.Travel-Guide-Accommodation) - [B&B in Stratton](https://www.expedia.ca/Stratton-Bed-And-Breakfast.d163002-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Stratton](https://www.expedia.ca/Stratton-Cabins.d163002-aaCabins.Travel-Guide-Accommodation) - [Chalets in Stratton](https://www.expedia.ca/Stratton-Chalets.d163002-aaChalets.Travel-Guide-Accommodation) - [Condo Rentals in Stratton](https://www.expedia.ca/Stratton-Condos.d163002-aaCondos.Travel-Guide-Accommodation) - [Country Houses in Stratton](https://www.expedia.ca/Stratton-Country-House.d163002-aaCountryHouse.Travel-Guide-Accommodation) - [Hostels in Stratton](https://www.expedia.ca/Stratton-Hostels.d163002-aaHostels.Travel-Guide-Accommodation) - [All Inclusive Resorts and in Stratton](https://www.expedia.ca/Stratton-Hotels-All-Inclusive-Hotel.0-0-d163002-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Cheap-Hotels.0-0-d163002-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Family-Hotel.0-0-d163002-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Golf-Hotel.0-0-d163002-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Hilton-Hotels.0-0-d163002--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Stratton](https://www.expedia.ca/Stratton-Hotels-Hotel-With-Early-Check-In.0-0-d163002-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Stratton](https://www.expedia.ca/Stratton-Hotels-Hotel-With-Pool.0-0-d163002-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Stratton](https://www.expedia.ca/Stratton-Hotels-Hotels-With-Childcare.0-0-d163002-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Stratton](https://www.expedia.ca/Stratton-Hotels-Hotels-With-Free-Breakfast.0-0-d163002-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Stratton](https://www.expedia.ca/Stratton-Hotels-Hotels-With-Free-Parking.0-0-d163002-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Luxury-Hotel.0-0-d163002-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Mountain-Hotels.0-0-d163002-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Pet-Friendly-Hotel.0-0-d163002-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Relais & Chateaux Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Relais-Chateaux.0-0-d163002--bRelaisChateaux.Travel-Guide-Filter-Hotels) - [Ski Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Ski-Hotel.0-0-d163002-tSkiHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Stratton](https://www.expedia.ca/Stratton-Hotels-Wedding-Hotels.0-0-d163002-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Stratton Hotels](https://www.expedia.ca/Stratton-Hotels.d163002.Travel-Guide-Hotels) - [Inns in Stratton](https://www.expedia.ca/Stratton-Inns.d163002-aaInns.Travel-Guide-Accommodation) - [Motels in Stratton](https://www.expedia.ca/Stratton-Motels.d163002-aaMotels.Travel-Guide-Accommodation) - [Hotels near Stratton Mountain Resort](https://www.expedia.ca/Stratton-Mountain-Resort-Hotels.0-l6115910-0.Travel-Guide-Filter-Hotels) - [Hotels near Stratton Mountain Summit Gondola](https://www.expedia.ca/Stratton-Mountain-Summit-Gondola-Hotels.0-l6328803-0.Travel-Guide-Filter-Hotels) - [Vacation Homes in Stratton](https://www.expedia.ca/Stratton-Private-Vacation-Homes.d163002-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Resorts in Stratton](https://www.expedia.ca/Stratton-Resort-Hotels.d163002-aaResortHotels.Travel-Guide-Accommodation) - [Townshend Hotels](https://www.expedia.ca/Townshend-Hotels.d553248634998697337.Travel-Guide-Hotels) - [Cabin Rentals in Wardsboro](https://www.expedia.ca/Wardsboro-Cabins.d3000459767-aaCabins.Travel-Guide-Accommodation) - [Hostels in Wardsboro](https://www.expedia.ca/Wardsboro-Hostels.d3000459767-aaHostels.Travel-Guide-Accommodation) - [Wardsboro Hotels](https://www.expedia.ca/Wardsboro-Hotels.d3000459767.Travel-Guide-Hotels) - [Motels in Wardsboro](https://www.expedia.ca/Wardsboro-Motels.d3000459767-aaMotels.Travel-Guide-Accommodation) - [B&B in West River Trail](https://www.expedia.ca/West-River-Trail-Bed-And-Breakfast.d826387202485702656-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Farmstay in West Townshend](https://www.expedia.ca/West-Townshend-Agritourism.d184080-aaAgritourism.Travel-Guide-Accommodation) - [Cheap Hotels in West Townshend](https://www.expedia.ca/West-Townshend-Hotels-Cheap-Hotels.0-0-d184080-tCheapHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in West Townshend](https://www.expedia.ca/West-Townshend-Hotels-Romantic-Hotel.0-0-d184080-tRomanticHotel.Travel-Guide-Filter-Hotels) - [West Townshend Hotels](https://www.expedia.ca/West-Townshend-Hotels.d184080.Travel-Guide-Hotels) - [West Townshend Hotels](https://www.expedia.ca/West-Townshend-Hotels.d553248635976474502.Travel-Guide-Hotels) - [Rv Parks in West Townshend](https://www.expedia.ca/West-Townshend-RV-Parks.d553248635976474502-aaRVParks.Travel-Guide-Accommodation) - [West Wardsboro Hotels](https://www.expedia.ca/West-Wardsboro-Hotels.d3000459788.Travel-Guide-Hotels) - [B&B in Windham](https://www.expedia.ca/Windham-Bed-And-Breakfast.d6150553-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Windham](https://www.expedia.ca/Windham-Hotels-Couples-Resorts-Hotels.0-0-d6150553-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Windham Hotels](https://www.expedia.ca/Windham-Hotels.d6150553.Travel-Guide-Hotels) - [Resorts in Windham](https://www.expedia.ca/Windham-Resort-Hotels.d6150553-aaResortHotels.Travel-Guide-Accommodation) - [Chalets in Winhall](https://www.expedia.ca/Winhall-Chalets.d553248635975874057-aaChalets.Travel-Guide-Accommodation) - [Winhall Hotels](https://www.expedia.ca/Winhall-Hotels.d553248635975874057.Travel-Guide-Hotels) - [Lodges in Winhall](https://www.expedia.ca/Winhall-Lodges.d553248635975874057-aaLodges.Travel-Guide-Accommodation) - [Flights to Stratton](https://www.expedia.ca/Cheap-Flights-To-Stratton.d163002.Travel-Guide-Flights) - [American Express Ski Lift](https://www.expedia.ca/American-Express-Ski-Lift-Stratton.d6328793.Vacation-Attraction) - [Visit Bondville](https://www.expedia.ca/Bondville.dx6049474) - [Visit Mountain Acres](https://www.expedia.ca/Jamaica-Mountain-Acres.dx553248635976471490) - [Margie's Muse Handweaving & Gallery](https://www.expedia.ca/Margies-Muse-Handweaving-Gallery-Jamaica.d553248621532666871.Vacation-Attraction) - [Visit South Londonderry](https://www.expedia.ca/South-Londonderry.dx184074) - [Stratton Vacations](https://www.expedia.ca/Stratton.d163002.Destination-Travel-Guides) - [Visit Stratton](https://www.expedia.ca/Stratton.dx163002) - [Tamarack Ski Lift](https://www.expedia.ca/Tamarack-Ski-Lift-Stratton.d6328810.Vacation-Attraction) - [Visit West River Trail](https://www.expedia.ca/West-River-Trail.dx826387202485702656) - [Ace Rental Cars in Stratton](https://www.expedia.ca/Ace-Car-Rentals-In-Stratton.d163002-c2.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Stratton](https://www.expedia.ca/Avis-Car-Rentals-In-Stratton.d163002-c41.Car-Rental-Guide-Suppliers) - [Car rental Windham](https://www.expedia.ca/Car-Rentals-In-Windham.d6150553.Car-Rental-Guide) - [Stratton Vacation Rentals](https://www.expedia.ca/Stratton-Vacation-Rentals.d163002.Travel-Guide-VacationRentals) - [West River Trail Vacation Rentals](https://www.expedia.ca/West-River-Trail-Vacation-Rentals.d826387202485702656.Travel-Guide-VacationRentals) - [Things to do in West Wardsboro](https://www.expedia.ca/Things-To-Do-In-West-Wardsboro.d3000459788.Travel-Guide-Activities) - [Book B&B in Jamaica on Expedia.com](https://www.expedia.com/Jamaica-Bed-And-Breakfast.d184052-aaBedAndBreakfast.Travel-Guide-Accommodation)