Title: Winchester B&B: Find the Best Bed and Breakfast from CA $199 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000447144.Destination-Travel-Guides) ![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.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 [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/f54cc2db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/b858846d.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 $183 CA $199 total includes taxes & fees Feb 1 - Feb 2 [](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) ![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) ![Reception hall](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/7fbb1dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonel Williams Inn [](https://www.expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) Brattleboro 9.8/10 Exceptional (343 reviews) "The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sahand CA $202 CA $223 total includes taxes & fees Feb 15 - Feb 16 [](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) ![Property entrance](https://images.trvl-media.com/lodging/14000000/13580000/13579000/13578971/efe7a33f.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) ### 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 $198 CA $218 total includes taxes & fees Feb 18 - Feb 19 [](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) ![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) ![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/2000000/1780000/1779400/1779393/5baffb47.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 $316 CA $348 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/b4d09cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/a2863eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/29f5823f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/0de4f49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monadnock Inn [](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information) Jaffrey 7.6/10 Good (278 reviews) "The Inn was cozy, the room was clean and comfortable. The owner was engaging and helpful. Would definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) E S [](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/cb90562c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/6f5762a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/54ed3ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 3](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/2641c002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Engel House [](https://www.expedia.ca/Jacksonville-Hotels-The-Engel-House.h67598596.Hotel-Information) Jacksonville 9.2/10 Wonderful (17 reviews) "The perfect Vermont Bed and Breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lee [](https://www.expedia.ca/Jacksonville-Hotels-The-Engel-House.h67598596.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/3e2c5f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/4886f728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sturbridge Queen](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/fb914a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/12886762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centennial House [](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information) Northfield 9.6/10 Exceptional (173 reviews) "great proprietors beautiful vintage home excellent breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JAMES CA $232 CA $246 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/6a4870a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 Queen Bed, Private Bathroom (Wisteria Room)](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/4e79f11c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/56f95948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/01fdfd63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Maguire House Bed & Breakfast [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.Hotel-Information) Ashburnham 10/10 Exceptional (36 reviews) "Wonderful bed and breakfast - and remarkable hosts! Definitely worth booking if you plan to be in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ranjit CA $371 CA $371 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.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 | Garden view](https://images.trvl-media.com/lodging/2000000/1580000/1576100/1576027/ef4a9650.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 $415 CA $450 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Keene-Hotels-Chesterfield-Inn.h1576027.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117420000/117416200/117416128/50737f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117420000/117416200/117416128/196117b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117420000/117416200/117416128/6882b7ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117420000/117416200/117416128/27ac2b0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private bedroom in the Green River Bridge Inn. A full breakfast is included. [](https://www.expedia.ca/Brattleboro-Hotels-Private-Bedroom-In-The-Green-River-Bridge-Inn-A-Full-Breakfast-Is-Included.h117416128.Hotel-Information) Guilford CA $371 CA $473 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Brattleboro-Hotels-Private-Bedroom-In-The-Green-River-Bridge-Inn-A-Full-Breakfast-Is-Included.h117416128.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=2026-02-14&endDate=2026-02-15®ionId=3000447144&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%2FWinchester-Bed-And-Breakfast.d3000447144-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d3000447144-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "Good" [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "What's clean staff was friendly food was good bar was nice the buildings a little bit old " [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![The Inn At Crumpin Fox](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg) ### The Inn At Crumpin Fox 10/10 Excellent "The room was very spacious and exceptionally clean. We enjoyed the sitting area by the large bay window. The gentleman at the counter was very friendly and helpful. He even shoveled the snow from my vehicle." [](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Great room, friendly & helpful staff, plus a great location in the community" [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Reasonably priced and clean." [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "Very clean room and super friendly staff!" [](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Not fancy but a great place to stay. Owners are very nice and accommodating. I’ve been a customer for 25 years" [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Colonel Williams Inn](https://images.trvl-media.com/lodging/17000000/16820000/16817100/16817080/0d3a6bb4_y.jpg) ### Colonel Williams Inn 10/10 Excellent "The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious." [](https://expedia.ca/Brattleboro-Hotels-Colonel-Williams-Inn.h16817080.Hotel-Information) ![Vikings Villages Resort](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "Perfect accommodation. Rare combo of rustic feel and both clean and dry. Beds just how we like it. Kitchen very well equipped. Perfect for 4 people. Nice bathroom. Hot shower. Grounds perfectly described as Viking village. Staff very welcoming. Nice fire at the fire pit and the sheep are sure to be a hit with the little ones. Would love to go back when a little less snow to explore the Hiking trails and spend a little more time outside" [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 1,073 | | ----------------- | ------- | | Accommodation | 13 B&B | | Lowest Price | CA $199 | | Highest Price | CA $473 | ## Frequently asked questions ### What is the nightly rate for a Bed & Breakfast in Winchester? ### What is the difference between a Winchester B&B and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Monadnock Region ](https://www.expedia.ca/3Star-Monadnock-Region-Hotels.s30-0-d553248635975749761.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Keene ](https://www.expedia.ca/4Star-Keene-Hotels.s40-0-d6057413.Travel-Guide-Filter-Hotels) - [Hotels near Asbury United Methodist Church ](https://www.expedia.ca/Asbury-United-Methodist-Church-Hotels.0-l6265749-0.Travel-Guide-Filter-Hotels) - 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