Photo by Brandon Miller

Search B&B in Middlebury

    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

Compare 5 B&B in Middlebury with updated reviews, rates, and availability.

Homestead Inn
Front of property
Homestead Inn
3.5 star property
9.2 out of 10, Wonderful, (170)
"My daughter and I had a wonderful time in New Milford and at the Homestead Inn. First and foremost, the staff was wonderful and welcoming. We were greeted upon arrival and Antonio offered many helpful suggestions regarding area eateries and things to do - even places to park on our side trip to Yale in New Haven! Catherine was also very accommodating, going to extra lengths to assure that my daughter with food allergies was safe. The property was very clean and the area very charming....
The price is SAR 730
SAR 839 total
includes taxes & fees
18 Nov - 19 Nov
Homestead Inn
Jay's Ranch
Terrace/patio
Jay's Ranch
3.5 star property
7.6 out of 10, Good, (34)
"The host is amazing. Super attentive property is beautiful "
The price is SAR 279
SAR 311 total
includes taxes & fees
24 Nov - 25 Nov
Jay's Ranch
2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space
Interior
2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space
The price is SAR 1,126
SAR 1,810 total
includes taxes & fees
18 Nov - 19 Nov
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
9.8 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
Sunny Peace Homestay
Exterior
Sunny Peace Homestay
3.0 star property
The price is SAR 473
SAR 531 total
includes taxes & fees
18 Nov - 19 Nov
Sunny Peace Homestay
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
Front of property
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1964)
"It is a great Apartment-hotel and the suites have the right amenities. One critic that I have would be that there would sometimes you could smell the cigarette smoke from other neighbours blowing into the furnace. Public transportation is limited and so it's best to have a car. Staff is super helpful and accommodating. "
The price is SAR 314
SAR 350 total
includes taxes & fees
24 Nov - 25 Nov
New Haven Village Suites
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Main deck w/ grill & sweeping lake views. Baby/dog gate at deck stairs.
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (73)
"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."
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!
Private Beach 100 yards from Cottage
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (86)
"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."
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: Jay’s Ranch: 3 rooms. 14.7 mi (23.7 km) from the heart of Middlebury.Homestead Inn: 16 rooms. 15.1 mi (24.3 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. Union Station Clocktower and Waterbury City Hall 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.