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 2020 property listings offer a large selection of 323 vacation rentals around Old Saybrook. From 193 house rentals to 96 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a beachfront property in Old Saybrook?

Clear waters, white sands and spectacular sunsets as your canvas. If this sounds like your own personal heaven, now's your opportunity to truly bliss out. Vrbo has 101 beachside rental properties. Alternatively, you may be searching for a different vibe. Vrbo has heaps of options to choose from, including:

  • 93 seaside vacation rentals.
  • 86 beach-view vacation rentals.
  • 84 beach vacation rentals.

Can I rent a house in Old Saybrook?

You can forget about standardized, cookie cutter hotel-chain rooms. Our house vacation rentals each have their own unique personalities — and all the space you could possibly need! There are 191 options currently listed on Vrbo. Prices start from $32 a night. Or maybe you'd rather one of the area's other sought-after lodging options, such as:

  • Cottage: 96 vacation homes. Prices start from $99 per night.
  • Apartment: 14 vacation homes. Prices start from $106 per night.
  • Hotel: 10 vacation homes. Prices start from $60 per night.

Can I stay in Old Saybrook in a large group?

The recipe for a memorable trip is catching up with close friends and family in a totally new place. If you'll be hitting the road with a big group, Vrbo can help out. 47 house vacation homes are ready to be booked. Presently, they're the most popular choice here for big groups. The rental property options that are perfect for large numbers around here include:

  • If yours is a group of 6, we have 98 vacation homes suitable for that size. Spend a night from just $101.
  • Looking for a place for 8 guests? We have 69 that will suit. The starting price is $150 per night.
  • Seeking properties for rent catering to 10 people? You'll be thrilled to learn we have 35 that will fit the bill. You can book one from just $190 per night.

So don't fear! When you travel with us you can bring your aunt, your sister and all your pals to Old Saybrook.

Where are the cheapest rentals in Old Saybrook?

There are friends, there is family and then there are friends that become family. Renew the connections with those who truly matter and plan a budget-friendly escape with Vrbo. Essex Village is a fantastic area to consider if you want to keep an eye on your budget. Vrbo has 3 rentals, and the average price is a modest $193 per night. Old Saybrook Center is another good option. We've got 29 rentals here, and the average price is around $271 a night.

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