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Check prices for these dates

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

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, (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 AED 629
AED 724 total
includes taxes & fees
2 Feb - 3 Feb
Homestead Inn
Sunny Peace Homestay
Exterior

Sunny Peace Homestay

3.0 star property
9.0 out of 10, Wonderful, (2)
"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 AED 463
AED 532 total
includes taxes & fees
3 Feb - 4 Feb
Sunny Peace Homestay
Jay's Ranch
Terrace/patio

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 AED 319
AED 367 total
includes taxes & fees
3 Feb - 4 Feb
Jay's Ranch
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Interior

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

The price is AED 2,571
AED 3,918 total
includes taxes & fees
2 Feb - 3 Feb
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.
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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, (2000)
"Love this place "
The price is AED 324
AED 373 total
includes taxes & fees
5 Feb - 6 Feb
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, (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
Room

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.