Title: Bennington Vacation Home Rentals from CA $270: Search Top Private Vacation Homes for Rent | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Bennington Vacation Rentals ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975849202&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Bennington Vacation Homes ![Exterior](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/bc7db0b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/5d20c202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/95993e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95870000/95861300/95861212/baa6ad4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Artist’s A-Frame Madison 10/10 Exceptional (24) "It was an amazingly simple and great experience from booking to leaving. We spent less then 12 hours there but will definitely book again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colleen R. CA $176 CA $342 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Madison-Hotels-5-Minutes-From-Downtown-Madison.h95861212.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/7adbb048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/c7ba1628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/493c29fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105110000/105105600/105105513/720ba05a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glenda’s Overlook..everything you need to make visiting Madison a great getaway! Madison 9.8/10 Exceptional (44) "It is a nice place. We were able to walk to the river and main street fairly easy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul W. CA $146 CA $313 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Madison-Hotels-Glendas-Overlookeverything-You-Need-To-Make-Visiting-Madison-A-Great-Getaway.h105105513.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/w904h683x60y0-d395362b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/w508h683x258y0-d21f6d1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/w905h683x59y0-17d1ca1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970271/w506h683x259y0-fdd3ea23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill Madison 10/10 Exceptional (12) "Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carissa N. CA $212 CA $504 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Madison-Hotels-Madison-Manor-II-By-The-River-Hot-Tub.h101970271.Hotel-Information) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/c63e60d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/141012ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/c2bd2c8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119720000/119711700/119711645/w2096h1179x230y0-662ca136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming new tiny house-Friendship IN Versailles CA $123 CA $270 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Versailles-Hotels-Charming-New-Tiny-House-Friendship-IN.h119711645.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970267/w505h683x259y0-62cc3726.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, table tennis, books](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970267/w905h683x59y0-d0e21009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970267/w905h683x60y0-bd353afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/102000000/101980000/101970300/101970267/w903h683x60y0-6b905508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit Madison 9.6/10 Exceptional (12) "We thoroughly enjoyed our time! Great place! We would definitely stay there again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Howard B. CA $225 CA $512 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Madison-Hotels-Madison-Manor-I-By-The-River-Hot-Tub.h101970267.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/fc516579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/82d5d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/04e57aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109530000/109527800/109527752/43e11a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly Warsaw 9.0/10 Wonderful (7) "We certainly enjoyed the great view. Beautiful‼Fully furnished with lots of options. And our hosts were instantly responsive to our questions. Checkin and out were flawless " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gene M. CA $190 CA $549 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Warsaw-Hotels-Waterfront-Cabin-W-A-View-Large-Family-Retreat-Pet-Friendly.h109527752.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/24acbc04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/1bd992b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/cfa9ec43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100810000/100806000/100805995/30878268.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway Sparta 9.8/10 Exceptional (9) "Wonderful vacation home. Very clean, great host that was very helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley C. CA $305 CA $625 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/Warsaw-Hotels-Lake-House-With-Private-Dock-Ark-Encounter-Creation-Museum-Warsaw-Getaway.h100805995.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/e9ef6b13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/8164c41b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/753344e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/89000000/88260000/88253400/88253382/679a3875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11 Aurora 10/10 Exceptional (50) "We had a great visit— thank you!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy D. CA $267 CA $689 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Aurora-Hotels-Riverview-Retreat-Riverviews-Near-Ski-SlopesCreation-MuseumArkZooCincinnati.h88253382.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/115000000/114230000/114226300/114226295/69df6283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114230000/114226300/114226295/c7504337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114230000/114226300/114226295/99ef377a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/115000000/114230000/114226300/114226295/0ffa3e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private 1 BR Home with Hot Tub,Firepit & 5 min to dwtn Madison 10/10 Exceptional (14) "This cottage was the perfect, private getaway for two! It was clean, cozy, and peaceful both inside and outside! The hot tub was great after a full day of hiking. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mikayla S. CA $280 CA $465 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Madison-Hotels-Hot-Tub-Firepitmassage-Chair-Peaceful-SettingRomantic-Getaway-Perfection.h114226295.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119950000/119941700/119941699/f3316ddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/120000000/119950000/119941700/119941699/37d7c767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/120000000/119950000/119941700/119941699/8f7a9875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/120000000/119950000/119941700/119941699/048677ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Storybook Cottage 1940 Stone Home w/Bar, Kids Area, River Views, Trail Aurora CA $294 CA $626 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Aurora-Hotels-Riverside-Storybook-Cottage.h119941699.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/122000000/121170000/121161600/121161591/d2b8093c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/122000000/121170000/121161600/121161591/939b0173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121170000/121161600/121161591/659b8a97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121170000/121161600/121161591/7aa6c1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown Madison CA $417 CA $1,006 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Madison-Hotels-Madison-Manor-By-The-River-Sleeps-Up-To-15.h121161591.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120340000/120340000/120339916/493ff523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/121000000/120340000/120340000/120339916/60fe92c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120340000/120340000/120339916/1668c1a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120340000/120340000/120339916/9f2e7a59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Madison Retreat – New Furnishings, Walk to Shops & Riverfront Madison 10/10 Exceptional (1) "Our stay at this beautiful old home on Main Street in Madison was fantastic. The property has been beautifully maintained and modernized just enough to be comfortable without losing the gorgeous, authentic feel of an old home that clearly has stories to tell.The rooms were spacious and incredibly comfortable, providing plenty of room to relax. The location simply can't be beat—we loved that we could easily walk to all the local shops and great restaurants.Finally, the hosts were wonderfully... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lee M. CA $439 CA $844 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Madison-Hotels-Historic-Madison-Retreat-New-Furnishings.h120339916.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=2025-11-12&endDate=2025-11-13®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-Private-Vacation-Homes.d553248635975849202-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBennington-Private-Vacation-Homes.d553248635975849202-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Bennington Hotel Reviews ![Belterra Casino Resort](//images.trvl-media.com/lodging/2000000/1160000/1152900/1152807/04047b8f_y.jpg) ### Belterra Casino Resort 10/10 Excellent "The room was clean and bed was comfy. Room maybe a bit outdated, but still nice. " [](https://expedia.ca/Madison-Hotels-Belterra-Casino-Resort.h1152807.Hotel-Information) ![Rising Star Casino Resort](//images.trvl-media.com/lodging/1000000/160000/151200/151163/34b9980a_y.jpg) ### Rising Star Casino Resort 10/10 Excellent "The room and property was very clean. The property is outdated but it was clean. Very quiet atmosphere." [](https://expedia.ca/Lawrenceburg-Hotels-Rising-Star-Casino-Resort.h151163.Hotel-Information) ![Holiday Inn Express Hotel & Suites Madison by IHG](//images.trvl-media.com/lodging/1000000/70000/67500/67428/10924f56_y.jpg) ### Holiday Inn Express Hotel & Suites Madison by IHG 10/10 Excellent "Good stay. No problems." [](https://expedia.ca/Madison-Hotels-Holiday-Inn-Express-Hotel-Suites-Madison.h67428.Hotel-Information) ![Hillside Inn](//images.trvl-media.com/lodging/1000000/900000/894200/894180/816c8f88_y.jpg) ### Hillside Inn 10/10 Excellent "N/a" [](https://expedia.ca/Madison-Hotels-Hillside-Inn.h894180.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/12100/12064/004d2728_y.jpg) ### Quality Inn 10/10 Excellent "Good price." [](https://expedia.ca/Carrollton-Hotels-Quality-Inn.h12064.Hotel-Information) ![Empire House Hotel](//images.trvl-media.com/lodging/5000000/4490000/4486800/4486724/dfef9c62_y.jpg) ### Empire House Hotel 10/10 Excellent "It was perfect for my needs. Low keyed, quiet and in a nice location. Marsha was so friendly! I will definitely stay again" [](https://expedia.ca/Lawrenceburg-Hotels-Empire-House-Hotel.h4486724.Hotel-Information) ![Fairfield Inn & Suites Madison Historic Eagle Cotton Mill](//images.trvl-media.com/lodging/62000000/61410000/61401300/61401267/d00884c3_y.jpg) ### Fairfield Inn & Suites Madison Historic Eagle Cotton Mill 10/10 Excellent "Beautiful facility and a beautiful area the boardwalk along the Mississippi river is awesome. Many eateries nearby traffic was moderate." [](https://expedia.ca/Madison-Hotels-Fairfield-Inn-Suites-Madison.h61401267.Hotel-Information) ![Holiday Inn Express & Suites Carrollton by IHG](//images.trvl-media.com/lodging/2000000/1840000/1838000/1837952/7a9b7ab2_y.jpg) ### Holiday Inn Express & Suites Carrollton by IHG 10/10 Excellent "The property was clean and new. The woman at the front desk was friendly and efficient. Great place to stay and would definitely stay again." [](https://expedia.ca/Carrollton-Hotels-Holiday-Inn-Express-Suites-Carrollton.h1837952.Hotel-Information) ![The Chandler Hotel](//images.trvl-media.com/lodging/94000000/93090000/93082900/93082881/8a800e75_y.jpg) ### The Chandler Hotel 10/10 Excellent "Lovely!" [](https://expedia.ca/Madison-Hotels-The-Chandler-Hotel.h93082881.Hotel-Information) ## Find out more about Bennington ## Bennington Vacation Homes information | Number of reviews | 166 | | --- | --- | | Accommodation | 55 Vacation Homes | | Lowest Price | CA $270 | | Highest Price | CA $1,006 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Milan](https://www.expedia.ca/3Star-Milan-Hotels.s30-0-d55839.Travel-Guide-Filter-Hotels) - [Condo Rentals in Aberdeen](https://www.expedia.ca/Aberdeen-Condos.d553248635975869098-aaCondos.Travel-Guide-Accommodation) - [Cheap Hotels in Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Cheap-Hotels.0-0-d553248635975869098-tCheapHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Aurora](https://www.expedia.ca/Aurora-Hotels-Pet-Friendly-Hotel.0-0-d75612-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Aurora](https://www.expedia.ca/Aurora-Hotels-Wedding-Hotels.0-0-d75612-tWeddingHotels.Travel-Guide-Filter-Hotels) - 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