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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

Our top choices for Middlebury bed & breakfast

Dining

1. Homestead Inn

Homestead Inn
3.5 star property
New Milford
9.2 out of 10, Wonderful, (203 reviews)
"It was an all around great place to stay. "
United States
gerard
The price is AED 756
AED 870 total
includes taxes & fees
10 Aug - 11 Aug
Homestead Inn
Garden

2. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.2 out of 10, Wonderful, (10 reviews)
"When I arrived after dark, it was hard to tell if I was at the right house. The bedroom was clean and quiet. Appears to be a shared bathroom but lucky one of the two bedrooms were vacant. Good for a quick stay."
United States
Dean
The price is AED 479
AED 762 total
includes taxes & fees
10 Aug - 11 Aug
Sunny Peace Homestay
Exterior detail

3. Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay . Communication with our host was easy & prompt. We would stay again “"
United States
Laurel B.
The price is AED 507
AED 656 total
includes taxes & fees
9 Aug - 10 Aug
Peaceful Modern Private Room with Comfort & Charm
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

Wyndham Southbury

Wyndham Southbury

8/10 Good
"It was a great experience the only issues we had was there was no heat in our room it wasn’t working no Netflix all they had was live tv they ran out of steak and for breakfast we were not allowed to bring hot food upstairs. Other then that it was great"
Tom 1-night trip
Posted 5 hours ago
Wyndham Southbury

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. Enjoy the outdoor pool and unique décor. Jay's Ranch: 3 rooms. Situated 14.7 mi (23.7 km) from the heart of Middlebury. Peaceful Modern Private Room with Comfort & Charm: 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. Glebe House Museum and The Gertrude Jekyll Garden and Palace Theatre 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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