Discover a selection of 290 vacation rentals in Old Saybrook, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $144 per night, and houses and cottages are popular options for a stay in Old Saybrook. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Old Saybrook
Destination guide

Seaside escapes in Old Saybrook

The charming town of Old Saybrook draws travelers to its historic streets, where days are filled with shopping at antique stores, hanging out on sandy beaches and playing rounds of mini-golf with the kids. There are lots of ways to enjoy the waters of the Connecticut River and Long Island Sound that meet here, whether you prefer to take a fishing trip on the ocean or enjoy the gorgeous sunset at the end of the day. When the time comes to select your Old Saybrook vacation rental, you'll find an array of options await, from picturesque cottages to homes within walking distance of the sea.

Things to do

Step back in time in Old Saybrook

Old Saybrook is a historic town and wandering the streets you'll run into dozens of buildings that date back 100 years or more. Just up the Connecticut River, you can visit an interesting historic structure built in the early 1900s at Gillette Castle State Park. You can join seasonal tours of the stone mansion, which has the look of a medieval castle on the outside, or walk around the grounds to check out some of the exhibits on the art trail, designed to recreate 19th-century pieces. There are also hiking paths around the site, and spots to stop for a picnic.


Waterfront fun in Old Saybrook

Surrounded on 2 sides by water, Old Saybrook is an ideal spot to enjoy some fun on the waves, whether paddling up the Connecticut River on a kayak, or floating off into the Long Island Sound and Atlantic Ocean beyond. Local marinas offer opportunities to head out to sea on charters, including fishing trips to reefs and islands and boat rides across the Sound to Long Island, where all sorts of amusements await. Nothing beats a sunset excursion, where you can watch the sky displaying dazzling shades of pink and orange from the deck as you glide over the waves.


Warm summers in Old Saybrook

Old Saybrook gets a taste of all 4 seasons, with warm summers in the 80s, winters that dip below freezing and pleasant springs and falls that bring fresh greens and colorful foliage to the surrounding landscape. Summer is a popular time to visit, since the waterfront destination boasts a sandy beach and opportunities to take boat trips on Long Island Sound, but the shoulder seasons can be ideal, too, if you plan to do some hiking along the river or shopping in town. If you visit during the warmer times of year, why not look for an Old Saybrook vacation rental with access to the water?

Natural features

Discover Old Saybrook's waterfront delights

Your Old Saybrook vacation rental is the perfect hub for all sorts of outdoor adventures, with a river running alongside, the ocean beyond and plenty of waterfront parks nearby. Head to Rocky Neck State Park, where the landscape covers everything from salt marshes to sandy shores. The swimming beach here has a gorgeous swath of white sand, perfect for building castles with the kids or napping under the sun, while hiking trails around the park lead to viewing platforms where you might see some of the osprey or herons that live here.

How to get there

Traveling to and around Old Saybrook

The nearest airport is in New London, CT (GON-Groton - New London), located 17.3 mi (27.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Fishers Island, NY (FID-Elizabeth Field), which is 18.3 mi (29.4 km) away.

If you prefer train travel, you can make your way to Old Saybrook Station.

How many vacation rentals are available around Old Saybrook, CT?

Our 2021 property listings offer a large selection of 290 vacation rentals around Old Saybrook. From 264 house rentals to 77 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Old Saybrook?

Vrbo offers a large selection of vacation rentals near lovely places in Old Saybrook. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Saybrook Country Barn: 748 vacation rentals
  • Old Saybrook Station: 750 vacation rentals
  • Essex Saybrook Antique Village Shopping Center: 714 vacation rentals
  • General William Hart House: 777 vacation rentals
  • Stay and Play LLC: 754 vacation rentals

But there are many other points of interest around Old Saybrook listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Old Saybrook?

Yes, of course. Vrbo has 264 Houses in Old Saybrook. Our other popular types of vacation rentals in Old Saybrook include:

  • Cottages: 77 rentals available
  • Cabins: 77 rentals available
  • Bungalows: 77 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Old Saybrook?

Yes, you can select your preferred vacation rental with pool among our 25 vacation rentals with pool available in Old Saybrook. Please use our search bar to access the selection of vacation rentals available.