Title: Winchester B&B: Find the Best Bed and Breakfast from CA $186 | 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) ![](https://mediaim.expedia.com/destination/2/ea42c861000f38e6206ed251ac7da597.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Donny Campos # Find a Bed and Breakfast in Winchester from CA $186 ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester B&B ![Dining](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/7ffddd76.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 9.6/10 Exceptional (8) "Lovely staff, amazing ambiance!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $170 CA $186 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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 (336) "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 $220 CA $242 total includes taxes & fees Nov 3 - Nov 4 [](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) ![Garden](https://images.trvl-media.com/lodging/39000000/38510000/38505500/38505466/ca21030b.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) ### The Carriage Barn Inn Keene 9.6/10 Exceptional (162) "Great BB. Very charming and cozy! Will definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $253 CA $274 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Keene-Hotels-The-Elm-City-Carriage-Barn.h38505466.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 $339 CA $373 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Brattleboro-Hotels-The-One-Cat-BB.h13578971.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/771bf86d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/c1aa607e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Courtyard View](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/c0c06736.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117300000/117293700/117293650/8c5e9bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Green River Bridge Inn Guilford 9.0/10 Wonderful (11) "Beautiful Inn and property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JaDean CA $378 CA $412 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Green-River-Bridge-Inn.h117293650.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) ![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 (55) "Outstanding breakfast in a charming home. A 15 minute walk excellent to restaurants and art galleries." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gianfranco CA $373 CA $411 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.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) ![Deerfield Suite](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/855d2e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/9e088ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/900000/894000/893968/231b3a01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centennial House Northfield 9.6/10 Exceptional (171) "The property was wonderful and the hosts exceptional❤️" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $256 CA $271 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Northfield-Hotels-Centennial-House.h893968.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/de4bc344.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) ![Standard Double Room, Ensuite (Duncan Room-206)](https://images.trvl-media.com/lodging/2000000/1960000/1952400/1952388/3951af0a.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 Jaffrey 7.6/10 Good (272) "It is a Beautiful Old Charm Inn. Everything was great. I would definitely come back and stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon-Ann C CA $192 CA $208 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Jaffrey-Hotels-Monadnock-Inn.h1952388.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/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/fdd13f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LED TV, fireplace, Netflix, Hulu](https://images.trvl-media.com/lodging/68000000/67600000/67598600/67598596/97e6f6a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Engel House Jacksonville 9.2/10 Wonderful (15) "The perfect Vermont Bed and Breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lee CA $243 CA $265 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Jacksonville-Hotels-The-Engel-House.h67598596.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/2d1a895c.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) ![In-room dining](https://images.trvl-media.com/lodging/3000000/2210000/2205700/2205666/b15a084f.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) ### The Maguire House Bed & Breakfast Ashburnham 10/10 Exceptional (36) "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 $373 CA $373 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Leominster-Hotels-The-Maguire-House-Bed-Breakfast.h2205666.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) ![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) ![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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne CA $421 CA $457 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Exterior](https://images.trvl-media.com/lodging/118000000/117420000/117416200/117416128/6882b7ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117420000/117416200/117416128/742d79e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117420000/117416200/117416128/0f74e9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private bedroom in the Green River Bridge Inn. A full breakfast is included. Guilford CA $385 CA $490 total includes taxes & fees Oct 31 - Nov 1 [](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=2025-11-07&endDate=2025-11-08®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 ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Is a great historic building with great charm. Hope to stay there again soon." [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Reasonable price for an overnight stay. Ample parking, very quiet and easy access to I 91." [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 10/10 Excellent "The room's view was perfect" [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "Very nice & quiet. Close to downtown. Didn’t eat breakfast. " [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "The on-site restaurant named Tempestas was excellent and a huge plus for our 3-night stay. We ate there every night and were pleased with the food, service, atmosphere and the prices were reasonable. On a broader note, the hotel was nice, staff very helpful and I should mention that the breakfast one of the best I've had on 3 continents, aided by a hostess who was friendly and took lots of pride in serving hot food and keeping the food and coffee fresh." [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Black Mountain Inn](//images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c_y.jpg) ### Black Mountain Inn 10/10 Excellent "Nice for one night" [](https://expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "Viking Villages is incredible. Location is beautiful and they have hit every little thing to add to ambiance. Lodging is cozy and has everything you need for a little getaway. We will be back, highly recommend. " [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Hampton Inn & Suites Greenfield](//images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "Nice, clean room and friendly staff." [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![The Inn At Crumpin Fox](//images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg) ### The Inn At Crumpin Fox 10/10 Excellent "Large and comfortable room, nice staff. Breakfast only on weekends…" [](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 1,043 | | --- | --- | | Accommodation | 12 B&B | | Lowest Price | CA $186 | | Highest Price | CA $490 | ## Frequently asked questions ### What is the nightly rate for a Bed & Breakfast in Winchester? > Prices for B&Bs in Winchester often vary, but you can find a great deal from CA $186 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winchester 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 Winchester B&B and a hotel? > Every Winchester 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 Winchester B&Bs. ## 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) - [Castles in Cheshire County](https://www.expedia.ca/Cheshire-County-Castles.d553248635976430851-aaCastles.Travel-Guide-Accommodation) - [B&B in Chesterfield](https://www.expedia.ca/Chesterfield-Bed-And-Breakfast.d6052872-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chesterfield Hotels](https://www.expedia.ca/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels) - 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