Middlesex County Vacation Rentals, Connecticut: homes, house rentals & more

Find the perfect place for your stay in Middlesex County by choosing from 197 houses, 29 apartments, and other vacation rentals. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a washer and dryer. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including accessible or non-smoking choices.

Find the best place to stay - Middlesex County

lakefront estate

Sleeps 10 · 5 bedrooms · 2+ bathrooms

The house from the driving shows the jelly shed and the corn crib.

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

Sleeps 14 · 5 bedrooms · 2 bathrooms

Popular Middlesex County destinations on Vrbo

This photo was taken during a nice fall weekend. The water level was low enough to cross to the other side to capture the falls from a different angle than most. Best time however is early morning before most people get there.

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Top rated rentals - Middlesex County

Lovely Weekend

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Book a vacation rental for your Middlesex County getaway

Learn about the unique charm of Middlesex County with a stay in a private vacation home. This city has something for everyone. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Middlesex County

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

Machimoodus State Park (4.8 mi / 7.7 km)
Essex Steam Train (8.4 mi / 13.6 km)
Chamard Vineyards (9.4 mi / 15.1 km)
Brownstone Exploration & Discovery Park (11.5 mi / 18.5 km)
Powder Ridge Mountain Park and Resort (12.1 mi / 19.5 km)
Château le' Gari' (12.9 mi / 20.7 km)

Exploring the natural features in Middlesex County

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Middlesex County. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:

Machimoodus State Park (4.8 mi / 7.7 km)
Gillette Castle State Park (4.9 mi / 7.9 km)
Devil's Hopyard State Park (9.8 mi / 15.8 km)
Wadsworth Falls State Park (10.7 mi / 17.1 km)
Goose Island (11.3 mi / 18.2 km)
Westbrook Town Beach (11.5 mi / 18.5 km)

Transportation options to and around Middlesex County

If you're traveling by train, make your way to Clinton Station or Old Saybrook Station and explore the city from there.

Frequently asked questions

What is the best area to stay in Middlesex County when booking a vacation rental?

Old Saybrook is among the more popular locations to select a vacation property in Middlesex County. Searching for some fun things to do in this destination? Don't miss Essex Steam Train and Hammonasset Beach State Park.

What is the most popular type of vacation rental accommodation in Middlesex County?

The most popular types of vacation rentals in Middlesex County are houses. Prefer something different? Vrbo has many options to match our guests' needs, so you'll see vacation properties in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — snap up yours today.

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

The average price for a vacation home in Middlesex County depends on a number of factors, including time of year, length of stay and property type. Whether you're dreaming about a sprawling villa with lots of space or a quaint cabin perfect for just you and the kids, just add your dates of travel to discover stays with great value.

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

The average price for a vacation home by the beach in Middlesex County will depend on when you'll be there and the type and size of property you're looking for. You can find prices quickly and easily on Vrbo by entering your travel dates and destination. Then make use of the filter tool to choose the number of bedrooms and amenities that you prefer, such as air conditioning, a pool and WiFi.

What are popular rental amenities in Middlesex County?

When it comes to rental amenities that guests are searching for in Middlesex County, a stovetop, a fridge and a microwave oven rank highest. With Vrbo vacation rentals, you'll enjoy choices to match your style and taste, whether you're vacationing with friends, family or even pets.

Are there large group vacation rentals in Middlesex County?

Middlesex County has 29 vacation rentals that can fit 10 or more people. These properties come with the space and privacy you need to share good times with family and friends.

What are the top attractions for families in Middlesex County?

Keep the kids amused at these top family-friendly attractions in Middlesex County:

Clinton Crossing Premium Outlets
TPC River Highlands
Essex Steam Train

Can I find two-bedroom vacation rentals in Middlesex County?

Gather your loved ones and enjoy peace, privacy and comfort in one of the 39 two-bedroom vacation properties Middlesex County has to offer.

Are there vacation rentals with WiFi in Middlesex County?

Whether you want to keep up with world events, send some emails or post a pic to social media, there are 104 vacation homes with WiFi in Middlesex County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

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

The minimum age can differ across properties on Vrbo, so double-check the rules of the vacation home in Middlesex County you want. But in general, it's 16, 18 or 21.

How long can I rent a vacation rental in Middlesex County for?

The amount of time you can stay in a Middlesex County vacation rental for depends on each property. Simply tap in your travel dates to view options that offer long-term stays. They include all the things you need to make your extended break more convenient and comfortable, like air conditioning and laundries. Some Vrbo vacation properties may also offer discounted weekly or monthly prices, so you can stay even longer for less.