Middlesex County Vacation Rentals, Connecticut: house rentals & more

Find the perfect place for your stay in Middlesex County by choosing from 212 houses, 26 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.

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Find the best place to stay - Middlesex County

Luxury Waterfront Home-August 18-23 still available.

Sleeps 10 · 4 bedrooms · 2+ bathrooms

Beachfront Classic New England Home With Direct Views Of Long Island Sound

Sleeps 12 · 5 bedrooms · 3+ bathrooms

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Sleeps 13 · 4 bedrooms · 2 bathrooms

NEW JULY/AUGUST 2025 DATES JUST ADDED! Stunning Waterfront Home/Private Beach!

Sleeps 5 · 3 bedrooms · 2 bathrooms

Level back yard with private water frontage and access.

Classic Lake House w/ private waterfront, 4 steps to water, FirePit/Kayaks/canoe

Sleeps 10 · 3 bedrooms · 2 bathrooms

Top rated rentals - Middlesex County

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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 (3.9 mi / 6.3 km)
Brownstone Exploration & Discovery Park (10 mi / 16.1 km)
Powder Ridge Mountain Park and Resort (11.2 mi / 18 km)
Château le' Gari' (11.8 mi / 18.9 km)
TPC River Highlands (13.3 mi / 21.4 km)
Dinosaur Place at Nature's Art (16.2 mi / 26 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:

Connecticut River State Wildlife Area (10.6 mi / 17.1 km)
Dinosaur State Park (10.8 mi / 17.5 km)
Lake Beseck Beach (11.2 mi / 18.1 km)
Lake Hayward (11.4 mi / 18.3 km)
Goose Island (12.6 mi / 20.3 km)
Westbrook Town Beach (13 mi / 20.9 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?

Clinton is one of the most popular areas to find a vacation home in Middlesex County. Looking for some awesome places to see here? Take time to visit Clinton Crossing Premium Outlets and Clinton Town Beach.

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

The most popular types of vacation rentals in Middlesex County are cottages. Want something different? Vrbo has plenty of options to match our guests’ unique requirements, so you’ll see vacation homes in lots of sizes and shapes. The ideal home away from home is waiting for you — lock in yours today.

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

A range of things can affect what you’ll pay for your vacation rental in Middlesex County, such as the length of stay, type of property and season. However, all our vacation homes have something in common — unbeatable value. Just add your travel dates to find your perfect match.

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

Prices for beach houses in Middlesex County may differ depending on the size and style of the property and when you’re traveling. Simply enter your travel dates into Vrbo and how many guests to view your options and prices. From there you can use our filter tool to narrow your search results by ratings, nearby activities and more.

Are there pet-friendly vacation rentals in Middlesex County?

Pack up a suitcase for your pup because Middlesex County has 44 properties that welcome pets with open arms. Let your furriest pal enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and travel dates, then check the “Pets allowed” filter box.

Are there large group vacation rentals in Middlesex County?

You can choose from 37 properties in Middlesex County that can accommodate a group of 10 or more people. Whether you’re organizing time away with the family or a special event like a birthday party, there’s plenty of room to get your favorite people together under the same roof.

Are there one-bedroom vacation rentals in Middlesex County?

You’ll find 34 one-bedroom properties in Middlesex County to pick from. A one-bedroom vacation property is a great choice if it’s only the two of you or if you’re traveling on your own. Toss in more convenience, space and privacy than a regular hotel, and you’ve got yourself an unforgettable getaway.

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

Choose from 52 two-bedroom rentals in Middlesex County. Give the kids the second room or fill it with a couple of your best friends. There’s a spot for whoever’s lucky enough to be coming along for the ride.

Are there vacation rentals with WiFi in Middlesex County?

Whether you want to keep up with the headlines, write a few emails or update your social media, there are 132 vacation homes with WiFi in Middlesex County. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.

How can I find vacation rentals with air conditioning in Middlesex County?

Middlesex County has 210 vacation rentals where you can relax in air-conditioned comfort. To book a stay on Vrbo featuring this amenity, enter your travel dates and use the convenient filters to select the “air conditioning” box.

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

The minimum required age is normally 16, 18 or 21. It can vary between properties on Vrbo, so look at the rules of your chosen Middlesex County vacation home before booking your escape.

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

The amount of time you can stay in a Middlesex County vacation home for differs depending on the property. Just enter your dates of travel to see available options that offer long-term stays. They come with all you require to make your extended vacation more convenient and enjoyable, such as air conditioning and kitchens. Some Vrbo vacation homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.

Does Vrbo offer discounts for vacation homes in Middlesex County?

On Vrbo, we’ve got some great discounts and deals for Middlesex County. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re looking for a weekend getaway or an extended escape, Vrbo offers a variety of options for every budget and style.