Book Middlesex County holiday rental accommodation: short-term rental properties & homes

Select from 212 homes, 87 cottages and other holiday rentals in Middlesex County to find one that's perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Popular Middlesex County destinations on Stayz

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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

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

Sleeps 12 · 6 bedrooms · 2 bathrooms

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

Sleeps 5 · 3 bedrooms · 2 bathrooms

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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Book a holiday rental for your Middlesex County getaway

Learn about the unique charm of Middlesex County with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway 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

Do you want to find attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that Middlesex County has to offer. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

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 appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Middlesex County. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

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)

Transport options to and around Middlesex County

If you prefer train travel, 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 holiday home?

Old Saybrook is among the more popular locations to select a holiday 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 holiday home accommodation in Middlesex County?

The most popular types of holiday homes in Middlesex County are houses. Prefer something different? Stayz has many options to match our guests’ needs, so you’ll see holiday 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 holiday home in Middlesex County?

The average price for a holiday 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 holiday 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 Stayz 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 home amenities in Middlesex County?

When it comes to home amenities that guests are searching for in Middlesex County, a stovetop, a fridge and a microwave oven rank highest. With Stayz holiday homes, you’ll enjoy choices to match your style and taste, whether you’re holidaying with friends, family or even pets.

Are there large group holiday homes in Middlesex County?

Middlesex County has 29 holiday homes 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 holiday homes in Middlesex County?

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

Are there holiday homes 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 holiday homes with WiFi in Middlesex County. Check the “WiFi” box when searching on Stayz and stay connected on your holiday.

How old do you have to be to rent a holiday home in Middlesex County?

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

How long can I rent a holiday home in Middlesex County for?

The amount of time you can stay in a Middlesex County holiday home 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 Stayz holiday properties may also offer discounted weekly or monthly prices, so you can stay even longer for less.