A weathered stone structure with steps and a small opening, surrounded by fallen leaves and moss.

Find a Bed and Breakfast in Middlebury from CA $249

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Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Middlebury bed & breakfast

A spacious living room with hardwood floors, a large dining area, and a cozy seating area with a red sofa and matching cushions.

1. Homestead Inn

Homestead Inn
3.5 star property
New Milford
9.2 out of 10, Wonderful, (206 reviews)
"It was an all around great place to stay. "
United States
gerard
Homestead Inn
A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

2. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.6 out of 10, Exceptional, (14 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 CA $181
CA $288 total
includes taxes & fees
Sep 29 - Sep 30
Sunny Peace Homestay
A building with a grey exterior, a front door, and a small porch with steps.

3. Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
8.4 out of 10, Very good, (6 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 CA $192
CA $249 total
includes taxes & fees
Sep 22 - Sep 23
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

Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

10/10 Excellent
"Everything was great here. We only stayed one night but it was clean and in a safe area."
Garnett 1-night trip
Posted 1 hour ago
Hilton Garden Inn Shelton

Find out more about Middlebury

Middlebury B&B information

Number of reviews
220
Accommodation
6 B&B
Lowest Price
CA $249
Highest Price
CA $288

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. Peaceful Modern Private Room with Comfort & Charm: Situated 16 mi (25.7 km) from the heart of Middlebury. 1 King & 1 Queen suit available in Guest House quiet & serene: 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 Beacon Falls Town Recreation Field 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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