Photo by Brandon Miller

Find a Bed and Breakfast in Middlebury from CA $106

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Browse Select Middlebury B&B

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 $106
CA $122 total
includes taxes & fees
Jan 8 - Jan 9, 2025
Jay's Ranch
Homestead Inn
Dining

Homestead Inn

3.5 star property
9.2 out of 10, Wonderful, (171)
"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 $246
CA $283 total
includes taxes & fees
Jan 12 - Jan 13, 2025
Homestead Inn
Sunny Peace Homestay
Living room

Sunny Peace Homestay

3.0 star property
10.0 out of 10, Exceptional, (1)
"Stayed there for business. Cute bed and breakfast! She made me tea when I got there late. Angie was a sweetheart Will def stay every time I have a shift at the hospital! "
The price is CA $181
CA $208 total
includes taxes & fees
Dec 30 - Dec 31
Sunny Peace Homestay
2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space
Property grounds

2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space

The price is CA $431
CA $694 total
includes taxes & fees
Dec 30 - Dec 31
2500 SF Loft: You Own Full 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.
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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, (1985)
"One of our favorites"
The price is CA $141
CA $162 total
includes taxes & fees
Dec 29 - Dec 30
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, (78)
"Thank you for allowing us to reside at your beautiful property. We appreciate your expedited communication & commitment to quality. We thank Jehovah for a safe enjoyable trip & as we return back to Atlanta, GA. "
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Beach nearby, beach towels

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (87)
"The parking situation was a bit tricky because there was no good way to back in. Other than that, location was great - cute area! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
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.Jay’s Ranch: 3 rooms. 14.7 mi (23.7 km) from the downtown core. 2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space: Situated 16.1 mi (25.9 km) from the heart of Middlebury. Sunny Peace Homestay: 2 rooms. 16 mi (25.7 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. Pilgrim Mall Shopping Center 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.