Title: 20 Best B&B in Middlebury, CT - Bed and Breakfast from $237 | 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 Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Middlebury bed & breakfast ![Dining](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/b1d5aed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/c1023943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Monroe Room | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/1b68d1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/85ffb075.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestead Inn [](https://www.expedia.com/Danbury-Hotels-Homestead-Inn.h1046891.Hotel-Information) New Milford 9.2/10 Wonderful (196 reviews) "Everything was as noted with a friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colby $206 nightly $237 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Homestead-Inn.h1046891.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/cb2d285a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/0729361e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/5aa07695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/056c3b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space [](https://www.expedia.com/Hamden-Hotels-2500-SF-Loft-You-Own-Full-Floor-Luxury-Oasis-In-A-Commercial-Space.h101878830.Hotel-Information) Hamden $858 nightly $971 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Hamden-Hotels-2500-SF-Loft-You-Own-Full-Floor-Luxury-Oasis-In-A-Commercial-Space.h101878830.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=2026-02-25&endDate=2026-02-26®ionId=183065&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&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) ![](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-Bed-And-Breakfast.d183065-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddlebury-Bed-And-Breakfast.d183065-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Middlebury Hotel Reviews ![Hampton Inn & Suites Hartford/Farmington](https://images.trvl-media.com/lodging/3000000/2980000/2970600/2970540/393f3b68_y.jpg) ### Hampton Inn & Suites Hartford/Farmington 10/10 Excellent "Excellent customer service " [](https://expedia.com/Hartford-Hotels-Hampton-Inn-And-Suites-HartfordFarmington.h2970540.Hotel-Information) ![Trumbull Marriott Shelton](https://images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg) ### Trumbull Marriott Shelton 10/10 Excellent "The room was clean, and the staff was kind." [](https://expedia.com/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information) ![Hyatt House Shelton](https://images.trvl-media.com/lodging/4000000/3490000/3482200/3482162/0d731ede_y.jpg) ### Hyatt House Shelton 10/10 Excellent "Absolutely amazing " [](https://expedia.com/New-Haven-Hotels-HYATT-House-Shelton.h3482162.Hotel-Information) ![Hamden Hotel and Suites – Hamden New Haven](https://images.trvl-media.com/lodging/1000000/20000/18000/17931/c3c836db_y.jpg) ### Hamden Hotel and Suites – Hamden New Haven 10/10 Excellent "Clean " [](https://expedia.com/New-Haven-Hotels-Clarion-Hotel-Suites-Hamden-New-Haven.h17931.Hotel-Information) ![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/c0e669e8_y.jpg) ### Courtyard by Marriott Waterbury Downtown 10/10 Excellent "It was clean and the staff was very kind" [](https://expedia.com/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.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 "Love the staff very nice and attentive. Very clean nice bar!!! Close to everything, I’ll definitely will stay there again!! " [](https://expedia.com/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![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 "What a great find and value for the money! Our room was so spacious with a sitting area and small kitchenette included, and the bountiful breakfast sealed the deal. We will definitely be back when we’re in the area." [](https://expedia.com/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/120068a2_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "Overall great stay. Staff was friendly and helpful, room was clean, breakfast was nice, and the gym was well taken care of. We had loud neighbors one night, but we called the desk and the helped us out instantly. Overall, we felt very comfortable here. " [](https://expedia.com/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Excellent desk staff. Clean and quite room. Good location." [](https://expedia.com/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ## Find out more about Middlebury ## Middlebury B&B information | Number of reviews | 196 | | ----------------- | ----- | | Accommodation | 4 B&B | | Lowest Price | $237 | | Highest Price | $971 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Middlebury? ### When is the best time to book a Bed & Breakfast in Middlebury? > September typically brings mild temperatures ranging from the low 50s to mid-70s Fahrenheit, creating a comfortable environment for outdoor activities. The pleasant climate allows for enjoyable exploration of Middlebury's historic sites, including the picturesque Middlebury College campus and the renowned Henry Sheldon Museum, which showcases the area's rich heritage. > > > If you're looking for a more budget-friendly option, consider visiting in early November. While this month marks the transition into winter, it offers a peaceful atmosphere superb for those seeking a quieter getaway. You can still enjoy hikes through the crisp autumn air, along with the chance to experience the local community's charm without the larger crowds. ### What is the difference between a Middlebury Bed and Breakfast and a hotel? ## 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) - [Flights to Connecticut ](https://www.expedia.com/Destinations-In-Connecticut.d208.Flight-Destinations) - [Flights from Waterbury - Oxford ](https://www.expedia.com/lp/airports/oxc/flights-from-waterbury-oxford-airport) - [Flights from Raleigh (RDU) to Oxford (OXC) ](https://www.expedia.com/lp/flights/rdu/oxc/raleigh-to-oxford) - 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[Flights from Daytona Beach (DAB) to Oxford (OXC) ](https://www.expedia.com/lp/flights/dab/oxc/daytona-beach-to-oxford) - [Flights from Oaxaca Intl. (OAX) to Oxford (OXC) ](https://www.expedia.com/lp/flights/oax/oxc/oaxaca-intl-to-oxford) - [Flights from Doha (DOH) to Oxford (OXC) ](https://www.expedia.com/lp/flights/doh/oxc/doha-to-oxford) - [Flights from Chicago (CHI) to Oxford (OXC) ](https://www.expedia.com/lp/flights/chi/oxc/chicago-to-oxford) - [Flights from San Juan (SJU) to Oxford (OXC) ](https://www.expedia.com/lp/flights/sju/oxc/san-juan-to-oxford) - [Flights from Norwood (OWD) to Oxford (OXC) ](https://www.expedia.com/lp/flights/owd/oxc/norwood-to-oxford) - [Flights from Roanoke (ROA) to Oxford (OXC) ](https://www.expedia.com/lp/flights/roa/oxc/roanoke-to-oxford) - [Flights from Las Vegas (LAS) to Oxford (OXC) ](https://www.expedia.com/lp/flights/las/oxc/las-vegas-to-oxford) - [Flights from Blantyre (BLZ) to Oxford (OXC) ](https://www.expedia.com/lp/flights/blz/oxc/blantyre-to-oxford) - [Quassy Amusement Park ](https://www.expedia.com/Quassy-Amusement-Park-Middlebury.d6089847.Vacation-Attraction) - [Hop Brook Lake ](https://www.expedia.com/Hop-Brook-Lake-Waterbury.d553248621561886346.Vacation-Attraction) - [Car rental Oxford Airport (OXC) ](https://www.expedia.com/Car-Rentals-In-Waterbury-Oxford.d6030940.Car-Rental-Guide)