Title: Winchester Guest Houses from CA $200 | 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 [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester guest houses ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/a0cdde49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/d7fa40cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/02cc9efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room | Private kitchenette](https://images.trvl-media.com/lodging/73000000/72620000/72611300/72611296/b9a1accb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Burrell House [](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information) Keene 9.6/10 Exceptional (159 reviews) "The building and room were very nice. The location is great, very walkable to the center of town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rochelle [](https://www.expedia.ca/Keene-Hotels-The-Burrell-House.h72611296.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/fdc80b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/7d4b7b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/c8b24996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blooming Inn [](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) Shelburne Falls 9.2/10 Wonderful (133 reviews) "Beautiful comfortable home with many thoughtful touches" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $128 CA $211 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/e8fee166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/2aeb1a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/d878b297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, foosball](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/7864ec9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn At Quail Run [](https://www.expedia.ca/Wilmington-Hotels-The-Inn-At-Quail-Run.h1153540.Hotel-Information) Wilmington 9.0/10 Wonderful (72 reviews) "Property was just as described, it was great staying there, outdoors was beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tami CA $268 CA $294 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Wilmington-Hotels-The-Inn-At-Quail-Run.h1153540.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/321c91e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/adbcecbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/2acfd77f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, streaming services](https://images.trvl-media.com/lodging/34000000/33400000/33395600/33395567/1d55e99a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### In town, newly remodeled studio with private balcony [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) Shelburne Falls 10/10 Exceptional (120 reviews) "set up great! very clean great location, WONDERFUL" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) laurie p. CA $117 CA $200 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Shelburne-Falls-Hotels-In-Town.h33395567.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/73000000/72020000/72018100/72018033/a373094e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace, books](https://images.trvl-media.com/lodging/73000000/72020000/72018100/72018033/f5a078cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72020000/72018100/72018033/02ea91e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72020000/72018100/72018033/c162053c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax in a Unique Treehouse Getaway - in Southwest NH [](https://www.expedia.ca/Nelson-Hotels-Relax-In-A-Unique-Treehouse-Getaway-In-Southwest-NH.h72018033.Hotel-Information) Munsonville 10/10 Exceptional (16 reviews) "Great little place to stay. Minimal living style away from it all." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan W. CA $309 CA $466 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Nelson-Hotels-Relax-In-A-Unique-Treehouse-Getaway-In-Southwest-NH.h72018033.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=2026-04-04&endDate=2026-04-05®ionId=3000447144&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d3000447144-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Guest-Houses.d3000447144-aaGuestHouses.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![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 8/10 Good "Good value." [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/ad889baf_y.jpg) ### The Colonial Hotel 10/10 Excellent "Staying at colonial hotel inbetween our wachusetts runs never disappoints. With great food, cozy atmosphere and decor, gym, pull and arcade, what else can one traveling with kids can ask for!" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca_y.jpg) ### Best Western Plus Keene Hotel 8/10 Good "I'm handicapped. Although they gave me a first-floor room, access from one's car via sliding glass door was problematic owing to a two-foot ridge of ice. They did shovel a path through for me, though. The sink wouldn't drain, but they it fixed quickly. The fridge froze everything inside it, no matter how adjusted. " [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Econo Lodge Brattleboro South](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/de359926_y.jpg) ### Econo Lodge Brattleboro South 2/10 Terrible "I HAVE BED BUG BITES!!!! Room was dirty Smoke alarm was missing. My key cards stopped working before I checked out." [](https://expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.Hotel-Information) ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8_y.jpg) ### Latchis Hotel 8/10 Good "The room was clean ans the bed very confortable " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c_y.jpg) ### The Putney Inn 6/10 Okay "Clean friendly a little worn" [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg) ### Days Inn by Wyndham Keene NH 4/10 Poor "Place has an off smell. People are loud and children are loud all night. Felt like there was some kind of party going on all night from different locations. Calling the front desk was met with attitude. Very dated. I got what I paid for as it was cheap. Location was great though." [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Gardner Inn](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07_y.jpg) ### Gardner Inn 6/10 Okay "Facility was clean. Rome was perfect for a night too beds in a bathroom TV and refrigerator no coffee pot. No vendor machines. " [](https://expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/50bc8764_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "Nice, quiet, clean spot handy to I91." [](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ## Find out more about Winchester ## Winchester Guest Houses information | Number of reviews | 500 | | ----------------- | -------------- | | Accommodation | 7 Guest Houses | | Lowest Price | CA $200 | | Highest Price | CA $466 | ## 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) - 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