Photo by Brandon Miller

Find a Bed and Breakfast in Middlebury from CA $125

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Middlebury B&B

Homestead Inn
Dining

Homestead Inn

3.5 star property
9.2 out of 10, Wonderful, (172)
"Super cute place. The onsite staff member was amazing. My only complaint is that our room smelled heavily of cigarettes. Not fresh. Like it was an old smoking room. We bought air freshener while we were out and had to spray repeatedly. Everything else was amazing "
The price is CA $247
CA $284 total
includes taxes & fees
Feb 2 - Feb 3
Homestead Inn
Sunny Peace Homestay
Living room

Sunny Peace Homestay

3.0 star property
9.0 out of 10, Wonderful, (2)
"A beautiful home in the woods of Northwest Connecticut. Quiet. Responsive and pleasant customer service. "
The price is CA $181
CA $209 total
includes taxes & fees
Feb 5 - Feb 6
Sunny Peace Homestay
Jay's Ranch
Private kitchen

Jay's Ranch

3.5 star property
7.8 out of 10, Good, (36)
"Best stay ever !!! Felt like I was family , she cooked us breakfast in the morning and also offered lunch and dinner , and also addressed that every Wednesday was laundry day and it was included with our stay, and told us if we pay for two days that we have the option to stay the third day free of charge "
The price is CA $125
CA $144 total
includes taxes & fees
Feb 3 - Feb 4
Jay's Ranch
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

The price is CA $1,008
CA $1,536 total
includes taxes & fees
Feb 3 - Feb 4
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Captain Josiah Cowles Place
Exterior

Captain Josiah Cowles Place

3.0 star property
10.0 out of 10, Exceptional, (19)
"This is a beautiful old home (c 1730), that is now used as an Inn-B&B establishment. It is very beautiful, clean and the owners provided a great breakfast and great hospitality ....which included the owners hand made Maple syrup made from the owners' Sugar Maples on the property. It was quite an experience, a real treat to be vacationing for a night in a home/Inn that was built before the Revolutionary War was even thought of and on the National Registry of Historic Homes/Buildings......It...
Captain Josiah Cowles Place
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.
Don't see what you're looking for?
See all available properties in Middlebury
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middlebury

New Haven Village Suites
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2000)
"Love this place "
The price is CA $127
CA $146 total
includes taxes & fees
Feb 5 - Feb 6
New Haven Village Suites
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun loungers

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

9.6 out of 10, Exceptional, (83)
"No complaints. Stayed during the winter so ne er got the full experience with the lake but it was a great home."
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Luxury Furnished Apartments by Hyatus Downtown at Yale
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (38)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale
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.

Frequently asked questions

Searching for B&Bs in Middlebury?
If you’re looking for something a little quirkier than the traditional hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some attractions in town, Quassy Amusement Park and Lake Quassapaug are worth a stop.
Why choose a B&B over a traditional hotel room?
With attentive service, opportunities to meet guests from other places, and breakfast served on site, B&Bs offer a unique environment.
What are the top B&Bs in Middlebury?
Below are some well-liked B&Bs in the area: Homestead Inn: 16 rooms. 15.1 mi (24.3 km) from the heart of Middlebury.Sunny Peace Homestay: 2 rooms. 16 mi (25.7 km) from the downtown core. Jay’s Ranch: 3 rooms. Situated 14.7 mi (23.7 km) from the heart of Middlebury. Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space: 16.1 mi (25.9 km) from the heart of downtown. Captain Josiah Cowles Place: 2 rooms. Located 12.3 mi (19.8 km) from the core of Middlebury. Enjoy the free full breakfast and library.
When should I book my B&B in Middlebury?
When you’re dreaming of a escape to Middlebury, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 32°F. Average annual precipitation for Middlebury is 56 inches.
What is there to do in Middlebury?
When you want to check out some attractions in town, you might consider a visit to Quassy Amusement Park and Lake Quassapaug. Hop Brook Lake and Hollow Park are also some sites to visit if you want to see more of the area.
How can I get to and around Middlebury?
Mapping out your trip in and around Middlebury is easy with these transportation options. Fly into Oxford, CT (OXC-Waterbury - Oxford), which is located 3.5 mi (5.6 km) from the heart of the city. You can also search for flights into Danbury, CT (DXR-Danbury Municipal), which is 21.4 mi (34.5 km) away. If you’d like to venture out around the area, you may want a rental car for your journey.