Title: Middlebury, CT Cottage Rentals from $510 | Expedia.com [Middlebury Travel Guide](https://expedia.com/Middlebury.dx183065)[Hotels in Middlebury](https://expedia.com/Middlebury-Hotels.d183065.Travel-Guide-Hotels)[Vacation Rentals in Middlebury](https://expedia.com/Middlebury-Vacation-Rentals.d183065.Travel-Guide-VacationRentals)[Flights to Middlebury](https://expedia.com/Cheap-Flights-To-Middlebury.d183065.Travel-Guide-Flights)[Car Rentals in Middlebury](https://expedia.com/Car-Rentals-In-Middlebury.d183065.Car-Rental-Guide)[Middlebury Vacation Packages](https://expedia.com/Middlebury.d183065.Destination-Travel-Guides) ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=183065&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 three months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=183065&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 four months [Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=183065&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) ## Our top choices for Middlebury cottages ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/1fc039de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/4172866e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/6e1b5e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/109000000/109000000/108996700/108996700/dc603626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Watertown Home w/ Yard: 1 Mi to Echo Lake Park! [](https://www.expedia.com/Oakville-Hotels-Watertown-Home-W-Yard-1-Mi-To-Echo-Lake-Park.h108996700.Hotel-Information) Oakville $443 nightly $510 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Oakville-Hotels-Watertown-Home-W-Yard-1-Mi-To-Echo-Lake-Park.h108996700.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=2026-03-10&endDate=2026-03-11®ionId=183065&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_183065) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America®ionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America®ionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APARTMENT) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America®ionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APART_HOTEL) Cottages [](https://www.expedia.com/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America®ionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=COTTAGE) Cabins [](https://www.expedia.com/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America®ionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CABIN) Condos [](https://www.expedia.com/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America®ionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CONDO) Villas [](https://www.expedia.com/Hotel-Search?destination=Middlebury%2C+Connecticut%2C+United+States+of+America®ionId=183065&latLong=41.527874%2C-73.127609&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&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%2FMiddlebury-Cottages.d183065-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddlebury-Cottages.d183065-aaCottages.Travel-Guide-Accommodation) ## Top Middlebury Hotel Reviews ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Very inviting lobby with several sitting areas. Front desk staff exceptionally pleasant & professional. Very clean room. Room attendants were really sweet & engaging. Grounds overall were well kept. The only issue we encountered was a toilet which would not flush;snaked it twice and awaiting an engineer to service it later today when he comes on shift. Overall, a pleasant stay, nice hotel and caring staff." [](https://expedia.com/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/40000/35400/35389/d1cdaed7_y.jpg) ### Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection 10/10 Excellent "Everything was amazing great stay !! " [](https://expedia.com/Southbury-Hotels-Heritage-Hotel.h35389.Hotel-Information) ![Homewood Suites by Hilton Orange New Haven](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979983/cf46bed4_y.jpg) ### Homewood Suites by Hilton Orange New Haven 10/10 Excellent "The room was clean, the pool and hot tub are open and maintained. Staff were kind and helpful. The breakfast was what you would expect for a hotel breakfast. We arrived at 4 and our room wasn't ready, but did not take log and getting a late checkout was easy. I would recommend staying here." [](https://expedia.com/New-Haven-Hotels-Homewood-Suites-By-Hilton-Orange-New-Haven.h38979983.Hotel-Information) ![Hyatt House Shelton](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/0d731ede_y.jpg) ### Hyatt House Shelton 10/10 Excellent "Room was very clean and staff were so so nice " [](https://expedia.com/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Great stay" [](https://expedia.com/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Great " [](https://expedia.com/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Cambria Hotel New Haven University Area](https://images.trvl-media.com/lodging/79000000/78620000/78614500/78614483/a6a28eee_y.jpg) ### Cambria Hotel New Haven University Area 10/10 Excellent "Very modern new clean facilities" [](https://expedia.com/New-Haven-Hotels-Cambria-Hotel-New-Haven-University-Area.h78614483.Hotel-Information) ![Trumbull Marriott Shelton](https://images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg) ### Trumbull Marriott Shelton 10/10 Excellent "Yes very clean " [](https://expedia.com/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information) ![Home2 Suites by Hilton East Haven New Haven](https://images.trvl-media.com/lodging/1000000/10000/1500/1461/b5c018f9_y.jpg) ### Home2 Suites by Hilton East Haven New Haven 10/10 Excellent "I had never stayed in a Home2 Suites location, so I had no idea what to expect. The room was spacious and clean. They had a great breakfast buffet area with tasty food options. The beds were super comfortable! I will definitely stay at a Home2 Suites again!" [](https://expedia.com/East-Haven-Hotels-Home2-Suites-By-Hilton-East-Haven-New-Haven.h1461.Hotel-Information) ## Find out more about Middlebury ## Middlebury Cottages information | Number of reviews | | | ----------------- | ----------- | | Accommodation | 53 Cottages | | Lowest Price | $510 | | Highest Price | $510 | ## Frequently asked questions ### How much do cottages in Middlebury cost? ### Why book your cottage in Middlebury with Expedia? ### How can I find cheap cottages in Middlebury? ### What is there to do in Middlebury near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Hotels near Quassy Amusement Park ](https://www.expedia.com/Quassy-Amusement-Park-Hotels.0-l6089847-0.Travel-Guide-Filter-Hotels) - [Hotels near Hop Brook Lake ](https://www.expedia.com/Hop-Brook-Lake-Hotels.0-l553248621561886346-0.Travel-Guide-Filter-Hotels) - [Hotels near Waterbury - Oxford ](https://www.expedia.com/Waterbury-Oxford-Airport-Hotels.0-aOXC-0.Travel-Guide-Filter-Hotels) - 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