Title: Bennington Cottages from CA $187 | Expedia.ca [Hotels in Bennington](https://expedia.ca/Bennington-Hotels.d553248635975849202.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.ca/Bennington-Vacation-Rentals.d553248635975849202.Travel-Guide-VacationRentals)[Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Bennington.d553248635975849202.Car-Rental-Guide)[Bennington Vacation Packages](https://expedia.ca/Bennington.d553248635975849202.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) # Search Bennington Cottage Rentals from CA $187 - ![](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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Bennington Cottages ![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98513500/98513412/3f14a7ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98520000/98513500/98513412/edfa868c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/99000000/98520000/98513500/98513412/ee1e7032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98520000/98513500/98513412/72adedd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Blue Door Place Florence 9.6/10 Exceptional (18) "Perfect spot " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damon G. CA $77 CA $187 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Florence-Hotels-The-Blue-Door-Place.h98513412.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/w1039h1041x15y0-0a46dd7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/w1014h1340x13y0-269a5c39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/f3088b94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122760000/122751500/122751483/w1018h1009x34y0-6c638f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison Madison CA $111 CA $223 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Madison-Hotels-Cute-CottagePet-FriendlyCleanTrails-Nature-And-Historic-Madison.h122751483.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=2025-12-19&endDate=2025-12-20®ionId=553248635975849202&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FBennington-Cottages.d553248635975849202-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBennington-Cottages.d553248635975849202-aaCottages.Travel-Guide-Accommodation) ## Top Bennington Hotel Reviews ![The Chandler Hotel](https://images.trvl-media.com/lodging/94000000/93090000/93082900/93082881/8a800e75_y.jpg) ### The Chandler Hotel 10/10 Excellent "The room and facility were amazing. Old world charm in the middle of downtown Madison, IN. Just about everything was within walking distance. We had a fantastic stay and thoroughly enjoyed our time spent here." [](https://expedia.ca/Madison-Hotels-The-Chandler-Hotel.h93082881.Hotel-Information) ![Hillside Inn](https://images.trvl-media.com/lodging/1000000/900000/894200/894180/816c8f88_y.jpg) ### Hillside Inn 10/10 Excellent "We had a wonderful time in Madison. The hotel is quite charming and the history behind it is so fascinating. There are some minor updates that need to be repaired in Room 104, but overall, it's fine. Merry Christmas! " [](https://expedia.ca/Madison-Hotels-Hillside-Inn.h894180.Hotel-Information) ![Fairfield Inn & Suites Madison Historic Eagle Cotton Mill](https://images.trvl-media.com/lodging/62000000/61410000/61401300/61401267/d00884c3_y.jpg) ### Fairfield Inn & Suites Madison Historic Eagle Cotton Mill 10/10 Excellent "Beautiful hotel, rooms were exceptionally clean, service was so friendly. Love this place and will return." [](https://expedia.ca/Madison-Hotels-Fairfield-Inn-Suites-Madison.h61401267.Hotel-Information) ![Riverboat Inn and Suites](https://images.trvl-media.com/lodging/107000000/106550000/106547800/106547778/5db58856_y.jpg) ### Riverboat Inn and Suites 10/10 Excellent "The place was amazing with beautiful views and charming artwork. The staff that we had the pleasure of meeting were incredible, especially Zach. He has to be one of the most pleasant young men I have met in my very long life. He truly brings joy to everyone he interacts with. Cannot wait to meet the owners on our next trip. We will be back when the weather is warm enough to truly enjoy the experience." [](https://expedia.ca/Madison-Hotels-Riverboat-Inn-And-Suites.h106547778.Hotel-Information) ![Holiday Inn Express Hotel & Suites Madison by IHG](https://images.trvl-media.com/lodging/1000000/70000/67500/67428/10924f56_y.jpg) ### Holiday Inn Express Hotel & Suites Madison by IHG 10/10 Excellent "Clean, comfortable, nicely updated room with coffee bar/mini fridge area. Friendly, helpful staff at check in. " [](https://expedia.ca/Madison-Hotels-Holiday-Inn-Express-Hotel-Suites-Madison.h67428.Hotel-Information) ![Rustic cabin just outside of Madison!](https://images.trvl-media.com/lodging/91000000/90910000/90904900/90904820/8faa0b34_y.jpg) ### Rustic cabin just outside of Madison! 10/10 Excellent "Beautiful cabin! " [](https://expedia.ca/Madison-Hotels-Rustic-Cabin-Across-The-Creek.h90904820.Hotel-Information) ![Belterra Casino Resort](https://images.trvl-media.com/lodging/2000000/1160000/1152900/1152807/04047b8f_y.jpg) ### Belterra Casino Resort 10/10 Excellent "Staff was very friendly and helpful. rooms were nice, very clean. Food was good. " [](https://expedia.ca/Madison-Hotels-Belterra-Casino-Resort.h1152807.Hotel-Information) ![Red Roof Inn Carrollton](https://images.trvl-media.com/lodging/1000000/800000/794400/794387/bb1e8c3d_y.jpg) ### Red Roof Inn Carrollton 10/10 Excellent "Clean and comfortable room, close to restaurants " [](https://expedia.ca/Carrollton-Hotels-Red-Roof-Inn-Carrollton.h794387.Hotel-Information) ![Hillcrest Motel By OYO Aurora IN Near Lawrenceburg](https://images.trvl-media.com/lodging/96000000/95330000/95324500/95324415/a4989d95_y.jpg) ### Hillcrest Motel By OYO Aurora IN Near Lawrenceburg 10/10 Excellent "The rooms were very clean indeed staff very friendly and cautious about handing out extra room key I found that to be a great quality they care about their tenants security " [](https://expedia.ca/Aurora-Hotels-Hillcrest-Motel.h95324415.Hotel-Information) ## Find out more about Bennington ## Bennington Cottages information | Number of reviews | 17 | | ----------------- | ---------- | | Accommodation | 9 Cottages | | Lowest Price | CA $187 | | Highest Price | CA $223 | ## Explore a world of travel with Expedia - 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