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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sep - 7 Sep
In two months
3 Oct - 5 Oct

B&B in Middlebury

Homestead Inn
Dining

Homestead Inn

3.5 star property
9.2 out of 10, Wonderful, (181)
"I didn’t even realize how cute the Inn was. Such a nice addition to my trip and a wonderful surprise "
The price is AED 756
AED 870 total
includes taxes & fees
17 Aug - 18 Aug
Homestead Inn
Jay's Ranch
Exterior

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (44)
"This was an amazing stay. Renee is a great host. She is clean, personable, and professional. The home is very cozy, and while still a work in progress, the outdoor area is beautiful and teeming with potential. This is not a hotel or a motel, understanding this, do not expect the starchy atmosphere of those places, but instead appreciate the friendly, homely vibe. If you’re looking for somewhere reasonably priced, clean, and cozy, this is a great spot."
Jay's Ranch
Sunny Peace Homestay
Exterior

Sunny Peace Homestay

2.0 star property
9.0 out of 10, Wonderful, (6)
"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! "
Sunny Peace Homestay
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Property grounds

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

The price is AED 2,314
AED 3,560 total
includes taxes & fees
10 Aug - 11 Aug
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

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"The staff was very friendly. Beds were so comfortable. "
John 2-night trip
Posted 1 day 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: 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. Sunny Peace Homestay: 2 rooms. Situated 16 mi (25.7 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.
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. Whittemore Glen State Park 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.