Middlebury holiday accommodation, Connecticut: holiday houses & more

Scroll through and select from holiday rentals in Middlebury to find one that's perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a hot tub. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

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Find the best place to stay - Middlebury

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Sleeps 2 · 1 bedroom · 1 bathroom

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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Middlebury getaway

The parks and surrounding scenery provide a peaceful ambience to your holiday home in Middlebury. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Middlebury

Are you looking for attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes Middlebury a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

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 an outdoor enthusiast or just want to appreciate the scenery, Middlebury is a great place to get outside. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

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)

Travelling to and around Middlebury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 3.5 mi (5.6 km) from the city centre. If you're unable to find a flight that fits your schedule, 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 holiday home in Middlebury?

Property type, season and length of stay are among the factors that can determine the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From cosy country cottages to plush villas, all Vrbo holiday homes 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 holiday home in Middlebury?

We recommend checking with the Middlebury holiday 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 holiday home 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.