Title: Rupert, VT Cottage Rentals from $189 | Expedia.com [Rupert Travel Guide](https://expedia.com/Rupert.dx3000459728)[Hotels in Rupert](https://expedia.com/Rupert-Hotels.d3000459728.Travel-Guide-Hotels)[Vacation Rentals in Rupert](https://expedia.com/Rupert-Vacation-Rentals.d3000459728.Travel-Guide-VacationRentals)[Flights to Rupert](https://expedia.com/Cheap-Flights-To-Rupert.d3000459728.Travel-Guide-Flights)[Car Rentals in Rupert](https://expedia.com/Car-Rentals-In-Rupert.d3000459728.Car-Rental-Guide)[Rupert Vacation Packages](https://expedia.com/Rupert.d3000459728.Destination-Travel-Guides) ![Vermont Foliage](https://images.trvl-media.com/place/3000459728/0596c53e-acf8-4425-a7ad-1840b2dc5352.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/3000459728/0596c53e-acf8-4425-a7ad-1840b2dc5352.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 [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=3000459728&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) In three months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=3000459728&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Rupert cottages ![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.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 Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Cambridge-Hotels-Peaceful-Cottage-Retreat.h33734584.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/c01ec95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/0a9e241b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/8b542543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82950000/82945200/82945159/1e1c1bc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome! [](https://www.expedia.com/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.Hotel-Information) Fort Ann 10/10 Exceptional (24 reviews) "Wonderful stay at a GREAT property!Couldn't ask for more!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert H. $323 nightly $359 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Fort-Ann-Hotels-Waterfront-Cottage-With-Fireplace-20-Min-From-Lake-George.h82945159.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=2026-04-08&endDate=2026-04-09®ionId=3000459728&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=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CABIN) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=VILLA) Chalets [](https://www.expedia.com/Hotel-Search?destination=Rupert%2C+Vermont%2C+United+States+of+America®ionId=3000459728&latLong=43.259796%2C-73.222885&adults=2&startDate=2026-06-23&d1=2026-06-23&endDate=2026-06-26&d2=2026-06-26&lodging=CHALET) ![](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%2FRupert-Cottages.d3000459728-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FRupert-Cottages.d3000459728-aaCottages.Travel-Guide-Accommodation) ## Top Rupert Hotel Reviews ![Weathervane Motel](https://images.trvl-media.com/lodging/11000000/10430000/10429400/10429394/17ddc189_y.jpg) ### Weathervane Motel 6/10 Okay "So this is a motel. That means all the windows look out at the parking lot. In order for this to work as designed, you need to have 2 layers of functional curtains; A heavy one and a sheer one. These curtains didn't work, so we couldn't see the lovely view. The HVAC did the job. The sheets were clean. A" [](https://expedia.com/Bennington-Hotels-Weathervane-Motel.h10429394.Hotel-Information) ![Hampton Inn and Suites Manchester](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Every employee was incredibly friendly, even if only passing us in the foyer or hallways. Stacy, the operations manager, was especially engaging, knowledgeable and helpful as we were deciding what to do for dinner and what events and venues were worth visiting. We took all of her suggestions and were thrilled when she was spot-on across the board, from Ye Olde Tavern to the syrup-making tour at Dutton’s to the Vermont Country Store. She’s an asset to your operations." [](https://expedia.com/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Toll Road Inn](https://images.trvl-media.com/lodging/8000000/7660000/7652200/7652200/94368990_y.jpg) ### Toll Road Inn 10/10 Excellent "Creek view from our room was beautiful. Bobs diner across the street for awesome breakfast before heading to Stratton 30 min away. Really cute lounge area and coffee and hot tub" [](https://expedia.com/Bennington-Hotels-Toll-Road-Inn.h7652200.Hotel-Information) ![Sun Lodge](https://images.trvl-media.com/lodging/2000000/1160000/1157400/1157354/6b0e0901_y.jpg) ### Sun Lodge 8/10 Good "Rooms are clean and staff helpful. Parking on site. Easy access to slopes." [](https://expedia.com/Bennington-Hotels-The-Lodge-At-Bromley.h1157354.Hotel-Information) ![The Palmer House Resort, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/4412313e_y.jpg) ### The Palmer House Resort, an Ascend Collection Hotel 4/10 Poor "Room was dusty ans did not appear to have been cleaned properly, had an allergy flair up. Found hairs in the bathroom. No other rooms available had to leave. Had to leave to another place. However staff was understanding, polite and tried to accommodate. It just didn’t work for us. " [](https://expedia.com/Bennington-Hotels-The-Palmer-House-Resort.h6028480.Hotel-Information) ![Four Winds Country Motel](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640832/c7e6e735_y.jpg) ### Four Winds Country Motel 10/10 Excellent "The mountains are gorgeous " [](https://expedia.com/Bennington-Hotels-Four-Winds-Country-Motel.h7640832.Hotel-Information) ![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg) ### Aspen At Manchester 6/10 Okay "Would not go back" [](https://expedia.com/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information) ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg) ### The Manchester View 10/10 Excellent "Beautiful property, clean room, friendly staff. Will definitely be staying here again!" [](https://expedia.com/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information) ![Brittany Motel](https://images.trvl-media.com/lodging/11000000/10540000/10533000/10532948/ef0071b7_y.jpg) ### Brittany Motel 10/10 Excellent "Perfect room for a few nights in Manchester. Room was clean and comfortable. Location was close to town and a short drive to the local ski mountains. The contactless check in/out was perfect for be because I arrived late and left early. Would definitely stay here again. " [](https://expedia.com/Bennington-Hotels-Brittany-Motel.h10532948.Hotel-Information) ## Find out more about Rupert ## Rupert Cottages information | Number of reviews | 71 | | ----------------- | ----------- | | Accommodation | 76 Cottages | | Lowest Price | $189 | | Highest Price | $359 | ## Frequently asked questions ### Why book your cottage in Rupert with Expedia? ### How can I find cheap cottages in Rupert? ### What is there to do in Rupert near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Merck Forest Farmland Center ](https://www.expedia.com/Merck-Forest-Farmland-Center-Hotels.0-l6265783-0.Travel-Guide-Filter-Hotels) - [B&B in Dorset ](https://www.expedia.com/Dorset-Bed-And-Breakfast.d184046-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Dorset ](https://www.expedia.com/Dorset-Cottages.d184046-aaCottages.Travel-Guide-Accommodation) - [Vacation Homes in Dorset ](https://www.expedia.com/Dorset-Private-Vacation-Homes.d184046-aaPrivateVacationHomes.Travel-Guide-Accommodation) - 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