Title: Bennington Cottages from CA $240 | Expedia.ca [Hotels in Bennington](https://expedia.ca/Bennington-Hotels.d6057349.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.ca/Bennington-Vacation-Rentals.d6057349.Travel-Guide-VacationRentals)[Flights to Bennington](https://expedia.ca/Cheap-Flights-To-Bennington.d6057349.Travel-Guide-Flights)[Things to do in Bennington](https://expedia.ca/Things-To-Do-In-Bennington.d6057349.Travel-Guide-Activities)[Bennington Car Rentals](https://expedia.ca/Car-Rentals-In-Bennington.d6057349.Car-Rental-Guide)[Bennington Vacation Packages](https://expedia.ca/Bennington.d6057349.Destination-Travel-Guides) ![Historic Henry Covered bridge over the Walloomsac River e in Bennington, Vermont](https://images.trvl-media.com/place/6057349/ddd79da6-d04a-4703-8452-12989539524e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6057349/ddd79da6-d04a-4703-8452-12989539524e.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 In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6057349&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Bennington cottages ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/8b8ec1dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4d94624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/0800588d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information) Stephentown CA $269 CA $758 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/758539b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/aed40cd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/defca110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/6958837e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Cottage Retreat [](https://www.expedia.ca/Cambridge-Hotels-Peaceful-Cottage-Retreat.h33734584.Hotel-Information) cambridge 9.8/10 Exceptional (47 reviews) "Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victor L. CA $154 CA $240 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Cambridge-Hotels-Peaceful-Cottage-Retreat.h33734584.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/171ffbfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/aa44f0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/f1003380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/82ebadba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom cottage with AC in charming Cavendish [](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) Cavendish CA $308 CA $833 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/e8e49a00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/620f7707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/070f19a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/109000000/108500000/108495200/108495123/413e13e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK [](https://www.expedia.ca/Jamaica-Hotels-Cozy-Cottage-7min-To-Ski-Stratton-Wood-Stove.h108495123.Hotel-Information) Jamaica 10/10 Exceptional (2 reviews) "The cottage was great and the hosts very communicative and checking in to make sure we were all set. We will be hopefully making this a yearly trip as we loved the seclusion and beautiful area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kyle M. CA $479 CA $723 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Jamaica-Hotels-Cozy-Cottage-7min-To-Ski-Stratton-Wood-Stove.h108495123.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92540000/92538900/92538895/ed5024bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/93000000/92540000/92538900/92538895/w1151h854x19y3-4c9d23b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92540000/92538900/92538895/fab80021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92540000/92538900/92538895/e0488b2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilltop Cottage [](https://www.expedia.ca/Argyle-Hotels-Hilltop-Cottage.h92538895.Hotel-Information) Argyle 10/10 Exceptional (3 reviews) "great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna Z. CA $753 CA $1,197 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Argyle-Hotels-Hilltop-Cottage.h92538895.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=2026-02-09&endDate=2026-02-10®ionId=6057349&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=VILLA) ![](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.d6057349-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBennington-Cottages.d6057349-aaCottages.Travel-Guide-Accommodation) ## Top Bennington Hotel Reviews ![Hampton Inn Bennington](https://images.trvl-media.com/lodging/2000000/1200000/1192000/1191981/aadd5504_y.jpg) ### Hampton Inn Bennington 10/10 Excellent "Room was great - no huge fee for pet" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-Bennington.h1191981.Hotel-Information) ![Knotty Pine](https://images.trvl-media.com/lodging/120000000/119110000/119106200/119106200/439bea3f_y.jpg) ### Knotty Pine 10/10 Excellent "The staff was very responsive, we had to check in late and the process was easy. " [](https://expedia.ca/Bennington-Hotels-Knotty-Pine.h119106200.Hotel-Information) ![Hotel Vervana, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/3000000/2580000/2577700/2577695/b33626c2_y.jpg) ### Hotel Vervana, Trademark Collection by Wyndham 10/10 Excellent "Very satisfied with our stay here. The property is comfortable and quiet, pet friendly and included both a jetted tub and a sauna in the room. The front desk staff was excellent and very friendly. Lots of dining options and shopping close by too. Would definitely stay here again next time we're in town. " [](https://expedia.ca/Bennington-Hotels-Paradise-Inn.h2577695.Hotel-Information) ![The Four Chimneys Inn](https://images.trvl-media.com/lodging/3000000/2400000/2394100/2394036/a1fa9bf1_y.jpg) ### The Four Chimneys Inn 10/10 Excellent "This is a quintessential Vermont inn in beautiful historic Bennington. The inn was lovingly cared for by the owner who was very attentive to his guests. We will stay again." [](https://expedia.ca/Bennington-Hotels-The-Four-Chimneys-Inn.h2394036.Hotel-Information) ![Harwood Hill Motel](https://images.trvl-media.com/lodging/13000000/12360000/12354600/12354542/ffee6d77_y.jpg) ### Harwood Hill Motel 10/10 Excellent "Clean room & courteous staff. " [](https://expedia.ca/Bennington-Hotels-Harwood-Hill-Motel.h12354542.Hotel-Information) ![South Shire](https://images.trvl-media.com/lodging/77000000/76170000/76163200/76163190/0f420ffa_y.jpg) ### South Shire 10/10 Excellent "A+ service, room we stayed in was perfect size with king bed. had an issue with heater first night but Inn Keeper was great to deal with and provided alternative heat source on first evening plus they have working fireplace (bonus++). We stayed 3 nights and just enjoyed ourselves during our visit. would definitely stay here again." [](https://expedia.ca/Bennington-Hotels-South-Shire.h76163190.Hotel-Information) ![Best Western Bennington](https://images.trvl-media.com/lodging/1000000/20000/16400/16323/5ad1b90e_y.jpg) ### Best Western Bennington 10/10 Excellent "Clean room and comfortable " [](https://expedia.ca/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information) ![One of a kind VT Renovated Barn- Cozy All Season and Holiday Retreat](https://images.trvl-media.com/lodging/55000000/54130000/54124000/54123926/8992719c_y.jpg) ### One of a kind VT Renovated Barn- Cozy All Season and Holiday Retreat 10/10 Excellent "Incredible converted barn made such an atmospheric place to stay after hiking the green mountains with our dog. All was clean and worked really well. We really enjoyed sitting by the huge fireplace every evening - we’d return immediately if we could!" [](https://expedia.ca/Bennington-Hotels-Cozy-One-Of-A-Kind-Renovated-Barn-Ultimate-Getaway.h54123926.Hotel-Information) ![Bennington Motor Inn](https://images.trvl-media.com/lodging/2000000/1530000/1523000/1522906/0219b10e_y.jpg) ### Bennington Motor Inn 10/10 Excellent "Great hotel for the price and convenient to downtown area.." [](https://expedia.ca/Bennington-Hotels-Bennington-Motor-Inn.h1522906.Hotel-Information) ## Find out more about Bennington ## Bennington Cottages information | Number of reviews | 48 | | ----------------- | ----------- | | Accommodation | 32 Cottages | | Lowest Price | CA $240 | | Highest Price | CA $1,197 | ## Frequently asked questions ### How much do cottages in Bennington cost? ### Why book your cottage in Bennington with Expedia? ### How can I find cheap cottages in Bennington? ### What is there to do in Bennington near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in West Arlington ](https://www.expedia.ca/4Star-West-Arlington-Hotels.s40-0-d553248635976385881.Travel-Guide-Filter-Hotels) - [B&B in Arlington ](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d74695-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hostels in Arlington ](https://www.expedia.ca/Arlington-Hostels.d74695-aaHostels.Travel-Guide-Accommodation) - 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