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 [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) In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=183065&startDate=2026-05-29&endDate=2026-05-31&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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1050000/1046900/1046891/c1023943.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 (198 reviews) "The Inn was very nice. I had stayed there about 13 years ago and was happy to see that the original warm feel had not changed with their expansion. The ammendities were great with free coffee and water. Great location with the ability to walk to restaurants and shopping. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennette $206 nightly $237 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Homestead-Inn.h1046891.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/127000000/126170000/126162500/126162410/79a3417b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave](https://images.trvl-media.com/lodging/127000000/126170000/126162500/126162410/fa99f5e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/127000000/126170000/126162500/126162410/0540df2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/127000000/126170000/126162500/126162410/7d62500d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Modern B&B with Comfort & Charm [](https://www.expedia.com/Harwinton-Hotels-Peaceful-Modern-BB-With-Comfort-Charm.h126162410.Hotel-Information) Harwinton $144 nightly $163 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Harwinton-Hotels-Peaceful-Modern-BB-With-Comfort-Charm.h126162410.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/102000000/101880000/101878900/101878830/5aa07695.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/ecd1ecf3.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 Apr 1 - Apr 2 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=2026-04-14&endDate=2026-04-15®ionId=183065&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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 ![The Farmington Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 8/10 Good "Loved the property and room cleanliness. Continental breakfast was acceptable, nothing to rave about (as I had read in some reviews): coffee was lukewarm at the very opening of the breakfast room, fresh fruit choice was limited to apples, the waffle machine wasn’t working properly and it took forever to make one waffle. This being said, the staff was kind and I would return to this lovely hotel when I’m in the area." [](https://expedia.com/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Holiday Inn Express Southington by IHG](https://images.trvl-media.com/lodging/1000000/10000/4000/3929/06fc08bd_y.jpg) ### Holiday Inn Express Southington by IHG 10/10 Excellent "breakfast was fine did not use a/c" [](https://expedia.com/Hartford-Hotels-Holiday-Inn-Express-Southington.h3929.Hotel-Information) ![Hyatt Place Milford / New Haven](https://images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/80833193_y.jpg) ### Hyatt Place Milford / New Haven 6/10 Okay "Staff were great, but rooms were pretty run down and need repairs. Lots of guests with terrible manners as far as noise and taking care of their children." [](https://expedia.com/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![Hilton Garden Inn Shelton](https://images.trvl-media.com/lodging/1000000/290000/287700/287687/18ff21f4_y.jpg) ### Hilton Garden Inn Shelton 10/10 Excellent "Slightly expensive but overall good" [](https://expedia.com/New-Haven-Hotels-Hilton-Garden-Inn-Shelton.h287687.Hotel-Information) ![Trumbull Marriott Shelton](https://images.trvl-media.com/lodging/1000000/10000/1200/1166/b3c487eb_y.jpg) ### Trumbull Marriott Shelton 4/10 Poor "When you walk in the front lobby, it smells like sewerage. The front desk people were nice. Restaurant and breakfast were good. Problems were they did not service our room, we had a queen sheet on a king bed and we asked them to change it because it popped off. The worse part was no hot tub and that is the only reason we stayed there. They blamed it on Expedia not changing it on their site. They said they would contact Expedia again. There were screaming young kids with no diapers in the pool. We had to leave it was so loud. " [](https://expedia.com/New-Haven-Hotels-Trumbull-Marriott-Shelton.h1166.Hotel-Information) ![Courtyard by Marriott Waterbury Downtown](https://images.trvl-media.com/lodging/1000000/40000/34300/34227/5fee96a0_y.jpg) ### Courtyard by Marriott Waterbury Downtown 10/10 Excellent "Always great." [](https://expedia.com/New-Haven-Hotels-Courtyard-By-Marriott-Waterbury-Downtown.h34227.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](https://images.trvl-media.com/lodging/1000000/10000/1300/1241/64f053d7_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 8/10 Good "Breakfast was great" [](https://expedia.com/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ![Best Western Executive Hotel Of New Haven - West Haven](https://images.trvl-media.com/lodging/1000000/30000/23300/23217/7d962b8e_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 8/10 Good "Old hotel. Very basic but clean. " [](https://expedia.com/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/b7b5473a_y.jpg) ### Omni New Haven Hotel at Yale 4/10 Poor "The hotel looked great, the staff was very friendly, the breakfast was great but the heat didn\`t work. The maintenance man brought up a portable heater. Therefore the overnight stay was terrible & we woke up in the morning sweating because the heat was working again." [](https://expedia.com/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ## Find out more about Middlebury ## Middlebury B&B information | Number of reviews | 198 | | ----------------- | ----- | | 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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