Middlebury Vacation Rentals, Connecticut: house rentals & more

Scroll through and select from vacation rentals in Middlebury to find one that's perfect for your trip. Vacation rentals provide the best amenities for your family, friends, or furry companion, like WiFi and parking. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Find the perfect vacation rental for your Middlebury getaway

The parks and surrounding scenery provide a peaceful ambiance to your vacation home in Middlebury. There's no shortage of things to see and do in the area.Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Middlebury

Are you hoping to discover things to do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Middlebury a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

Quassy Amusement Park (1.2 mi / 1.9 km)
Mount Southington Ski Area (11.1 mi / 17.9 km)
Lake Compounce (13 mi / 20.9 km)
Crystal Bees (14.6 mi / 23.5 km)
Yale Golf Course (16.2 mi / 26.1 km)
Hopkins Vineyard (16.9 mi / 27.2 km)

Exploring the natural features in Middlebury

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Middlebury is a great spot to appreciate mother nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

Hop Brook Lake (3.1 mi / 4.9 km)
Holy Land USA (5.2 mi / 8.4 km)
Southford Falls State Park (5.4 mi / 8.6 km)
Lake Lillinonah (11.4 mi / 18.4 km)
Steep Rock Preserve (12.1 mi / 19.5 km)
Bantam Lake (13.1 mi / 21.1 km)

Traveling to and around Middlebury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 3.5 mi (5.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Danbury, CT (DXR-Danbury Municipal), which is 21.4 mi (34.5 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Middlebury?

Property type, season and length of stay are among the factors that can determine the price of a vacation home. Simply enter your dates of travel to find your ideal fit. From cozy country cottages to plush villas, all Vrbo vacation rentals provide unbeatable value.

How much does it cost to rent a beach house in Middlebury?

When you travel and the size and style of the property will determine the cost of your beachside escape. Click on your Middlebury travel dates to view your available options on Vrbo. Can't live without a private pool? Use our filters to select the features and amenities you need.

What are the top attractions for families in Middlebury?

Keep the kids entertained at these fabulous family-friendly attractions in Middlebury:

Quassy Amusement Park
Mattatuck Beach
Old Bethlehem Historical Society Museum

How old do you have to be to rent a vacation rental in Middlebury?

We recommend checking with the Middlebury vacation home you're looking at on Vrbo as the minimum age differs. However, it's typically 16, 18 or 21.

How long can I rent a vacation rental in Middlebury for?

It really depends on the Middlebury property. To look over a list of options offering extended stays, just enter your dates and number of guests into Vrbo's search page. You can enjoy having the entire place to yourself, along with home comforts like a full kitchen, air conditioning and outdoor spaces where the kids can run around and play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.