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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Middlebury

Dining
Homestead Inn

Homestead Inn

3.5 star property
New Milford
9.2 out of 10, Wonderful, (196)
"Everything was as noted with a friendly staff"
United States
Colby
The price is SAR 773
SAR 889 total
includes taxes & fees
6 Jan - 7 January 2026
Homestead Inn
Property grounds
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

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

Hamden
The price is SAR 2,365
SAR 3,664 total
includes taxes & fees
8 Dec - 9 Dec
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Very clean room attentive staff and very accommodating. "
Melody Angela 1-night trip
Posted 8 hours ago
New Haven Hotel

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.Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space: 16.1 mi (25.9 km) from the downtown core. Jay's Ranch: 3 rooms. Situated 14.7 mi (23.7 km) from the heart of Middlebury. Sunny Peace Homestay: 2 rooms. 16 mi (25.7 km) from the heart of downtown.
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. Palace Theatre and Southford Falls State 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.