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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

B&B in Middlebury

Jay's Ranch
Exterior

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (44)
"This was an amazing stay. Renee is a great host. She is clean, personable, and professional. The home is very cozy, and while still a work in progress, the outdoor area is beautiful and teeming with potential. This is not a hotel or a motel, understanding this, do not expect the starchy atmosphere of those places, but instead appreciate the friendly, homely vibe. If you’re looking for somewhere reasonably priced, clean, and cozy, this is a great spot."
$109 nightly
The price is $125
Aug 24 - Aug 25
Total includes taxes and fees
Jay's Ranch
Homestead Inn
Dining

Homestead Inn

3.5 star property
9.2 out of 10, Wonderful, (183)
"I wish it was more apparent on Expedia's site that breakfast wasnt included in the annex rooms. I didnt realize until after I booked. Other than that the stay was fine."
$206 nightly
The price is $237
Aug 20 - Aug 21
Total includes taxes and fees
Homestead Inn
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Property grounds

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

$846 nightly
The price is $959
Aug 20 - Aug 21
Total includes taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
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.
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Top Middlebury Hotel Reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Very near to Yale. Clean rooms"
Bharathi 3-night trip
Posted 14 hours ago
Omni New Haven Hotel at Yale

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Middlebury?
Prices for B&Bs in Middlebury often vary, but you can find a great deal from $125 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Middlebury B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Middlebury?
The best time to book a B&B in Middlebury is during the vibrant fall season, particularly from September to October. This period captivates travelers with its stunning autumn foliage, making it ideal for scenic drives, hiking, and leisurely strolls through the charming town. As the leaves transform into a kaleidoscope of colors, visitors can immerse themselves in the natural beauty of the surrounding landscapes.

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?
Every Middlebury B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Middlebury B&Bs.