Title: Bennington, VT Cottage Rentals from $189 | Expedia.com [Bennington Travel Guide](https://expedia.com/Bennington.dx6057349)[Hotels in Bennington](https://expedia.com/Bennington-Hotels.d6057349.Travel-Guide-Hotels)[Vacation Rentals in Bennington](https://expedia.com/Bennington-Vacation-Rentals.d6057349.Travel-Guide-VacationRentals)[Flights to Bennington](https://expedia.com/Cheap-Flights-To-Bennington.d6057349.Travel-Guide-Flights)[Things to do in Bennington](https://expedia.com/Things-To-Do-In-Bennington.d6057349.Travel-Guide-Activities)[Car Rentals in Bennington](https://expedia.com/Car-Rentals-In-Bennington.d6057349.Car-Rental-Guide)[Bennington Vacation Packages](https://expedia.com/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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6057349&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6057349&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6057349&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6057349&startDate=2026-05-29&endDate=2026-05-31&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) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.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) ### 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck [](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information) Stephentown $499 nightly $554 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/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) ![Interior](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/6958837e.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33740000/33734600/33734584/79c166d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Cottage Retreat [](https://www.expedia.com/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. $170 nightly $189 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/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) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/82ebadba.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) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/120000000/119140000/119130500/119130417/6b5c4803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 3-bedroom cottage with AC in charming Cavendish [](https://www.expedia.com/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.Hotel-Information) Cavendish $543 nightly $608 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Cavendish-Hotels-Terrific-3-Bedroom-Cottage-With-AC-In-Charming-Cavendish.h119130417.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/93000000/92540000/92538900/92538895/17fb66d3.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.com/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. $800 nightly $888 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22®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.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CONDO) Chalets [](https://www.expedia.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CHALET) Apartments [](https://www.expedia.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APART_HOTEL) Villas [](https://www.expedia.com/Hotel-Search?destination=Bennington%2C+Vermont%2C+United+States+of+America®ionId=6057349&latLong=42.883412%2C-73.213441&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FBennington-Cottages.d6057349-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FBennington-Cottages.d6057349-aaCottages.Travel-Guide-Accommodation) ## Top Bennington Hotel Reviews ![Starlight Inn](https://images.trvl-media.com/lodging/2000000/1510000/1507900/1507889/ae52b0fb_y.jpg) ### Starlight Inn 10/10 Excellent "Clean " [](https://expedia.com/Bennington-Hotels-Starlight-Inn.h1507889.Hotel-Information) ![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "." [](https://expedia.com/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![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.com/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 "Room was spotless and very comfortable and spacious. Water pressure and temp were great. We were there on a zero degree night and the room temp was nice and warm. we’ll be back for sure and recommend to others!" [](https://expedia.com/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.com/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.com/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.com/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.com/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.com/Bennington-Hotels-Best-Western-Bennington.h16323.Hotel-Information) ## Find out more about Bennington ## Bennington Cottages information | Number of reviews | 46 | | ----------------- | ----------- | | Accommodation | 32 Cottages | | Lowest Price | $189 | | Highest Price | $888 | ## 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 - Vacation Rentals - [Hotels near Old First Congregational Church ](https://www.expedia.com/Old-First-Congregational-Church-Hotels.0-l6329594-0.Travel-Guide-Filter-Hotels) - 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