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Check prices for these dates

Next weekend
15 May - 17 May
In two weeks
22 May - 24 May
In one month
5 Jun - 7 Jun
In two months
3 Jul - 5 Jul

Our top choices for Middlebury bed & breakfast

Dining

Homestead Inn

Homestead Inn
3.5 star property
New Milford
9.2 out of 10, Wonderful, (198 reviews)
"The Inn was very nice. I had stayed there about 13 years ago and was happy to see that the original warm feel had not changed with their expansion. The ammendities were great with free coffee and water. Great location with the ability to walk to restaurants and shopping. "
United States
Jennette
The price is AED 756
AED 870 total
includes taxes & fees
10 May - 11 May
Homestead Inn
Fireplace

Peaceful Modern B&B with Comfort & Charm

Peaceful Modern B&B with Comfort & Charm
Harwinton
8.0 out of 10, Very Good, (1 review)
The price is AED 456
AED 598 total
includes taxes & fees
11 May - 12 May
Peaceful Modern B&B with Comfort & Charm
Interior

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 AED 2,314
AED 3,542 total
includes taxes & fees
10 May - 11 May
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Excellent service !! "
Russell 4-night trip
Posted 2 hours ago
Best Western Executive Hotel Of New Haven - West Haven

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?
Here are some well-liked B&Bs in the surrounding area: Homestead Inn: 16 rooms. 15.1 mi (24.3 km) from the heart of Middlebury.Peaceful Modern B&B with Comfort & Charm: 16 mi (25.7 km) from the downtown core. Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space: 16.1 mi (25.9 km) from the heart of downtown. Jay's Ranch: 3 rooms. Located 14.7 mi (23.7 km) from the core of Middlebury.
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 Holy Land USA 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.

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