Old Saybrook Vacation Rentals, Connecticut: house rentals & more

Select from 55 homes, 23 cottages, and other vacation rentals in Old Saybrook to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Old Saybrook

Showing deals for:Jul 25 - Aug 1

Exceptional

(20 reviews)

1 bedroom apartment on the water

Old Lyme, CT

5% off

Raised deck dining and lounging set; additional dining chairs not pictured

Exceptional

(42 reviews)

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

Guilford, CT

10% off

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Old Saybrook

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

Sleeps 12 · 5 bedrooms · 3+ bathrooms

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

Sleeps 8 · 5 bedrooms · 2 bathrooms

Top rated rentals - Old Saybrook

Premier Host

Excellent!

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Enjoy full kitchens, laundry, pools, yards and more
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A place for everyone
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Travel to beautiful Old Saybrook

Enjoy the history and other features of Old Saybrook. This city is scenic and relaxing, recognized for its beaches, golfing and shopping. 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.

Activities and attractions in Old Saybrook

Are you hoping to find top things to see and do in the area? Venture out of your cozy vacation rental and experience everything that makes Old Saybrook a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Dinosaur Place at Nature's Art (12.3 mi / 19.9 km)
Kontokosta Winery (12.6 mi / 20.2 km)
Gardiner's Bay Country Club (14.4 mi / 23.1 km)
Machimoodus State Park (14.7 mi / 23.7 km)
Sparkling Pointe (16.6 mi / 26.8 km)
Saybrook Country Barn (0.1 mi / 0.1 km)

Exploring the beaches and other natural features in Old Saybrook

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Old Saybrook is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city center:

Harvey's Beach (1.9 mi / 3 km)
Goose Island (3.1 mi / 4.9 km)
Westbrook Town Beach (4.3 mi / 7 km)
Clinton Town Beach (7.7 mi / 12.3 km)
McCook Point Beach (9.3 mi / 15 km)
Hammonasset Beach (9.4 mi / 15.1 km)

Seasonal weather averages in Old Saybrook

If you're planning a vacation around warm-weather activities, July, August, June and September are the hottest months to visit, when temperatures average 70°F.

How to get 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's convenient for your trip, you could book a flight to Fishers Island, NY (FID-Elizabeth Field), which is 18.3 mi (29.4 km) away.

If you'd prefer to travel by train, the main station serving the city is Old Saybrook Station.

Frequently asked questions

What is the best area to stay in Old Saybrook when booking a vacation rental?

One of the most desired areas to get a vacation home in Old Saybrook is Saybrook Manor. Find an ideal stay with Vrbo and explore this area like a local.

What is the most popular type of vacation rental accommodation in Old Saybrook?

Cottages are the most popular type of vacation rental in Old Saybrook, according to our data. Even if you’ve got a different vision in mind, Vrbo has vacation homes in all shapes and sizes. Take a look at our options to find your ideal fit.

How much does it cost to rent a vacation rental in Old Saybrook?

Different things can affect what you’ll pay for your vacation rental in Old Saybrook, including the length of stay, season and type of property. But, all Vrbo homes have one thing in common — excellent value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Old Saybrook?

When you travel and the size and style of the property will determine the cost of your beachside vacation rental. Click on your Old Saybrook travel dates to view your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to select the features and amenities you want.

Are there pet-friendly vacation rentals in Old Saybrook?

Pack a travel bag for your beloved pooch because Old Saybrook has 40 stays that roll out the welcome mat to pets. Let your furriest pal join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check our “Pets allowed” filter box.

Can I rent a house with a pool in Old Saybrook?

Pack your swimwear and inflatable swan, because there are five houses with a private pool in Old Saybrook. Make a booking at one of these popular vacation rentals and let every day be a pool day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the perfect place to make a splash!

Are there vacation rentals in Old Saybrook that welcome kids?

Bring the whole group together for an unforgettable adventure in Old Saybrook at one of our 40 family-friendly vacation homes. Lots of these stays provide conveniences that are perfect for trips with children, including laundries, living rooms and swimming pools. Just check the “Properties good for families” filter and pick out your favorite.

What are the top attractions for families in Old Saybrook?

Keep the kids busy at these fun family-friendly attractions in Old Saybrook:

Harvey’s Beach
Katharine Hepburn Cultural Arts Center
Chalker Beach

Are there vacation rentals with WiFi in Old Saybrook?

Whether you’d like to keep up to date with the news, reply to emails or surf social networks, there are 26 vacation homes with WiFi in Old Saybrook. Check the “WiFi” box when searching on Vrbo and stay connected on your getaway.

How can I find vacation rentals with air conditioning in Old Saybrook?

You’ll have a choice of 33 Vrbo vacation rentals with air conditioning in Old Saybrook offering that cool, cool breeze and extra bit of comfort. Enter your travel dates and then use our handy filter tool to look for properties with air conditioning.

How old do you have to be to rent a vacation rental in Old Saybrook?

The minimum required age is normally 16, 18 or 21. It can vary from one property to another on Vrbo, so look at the rules of your preferred Old Saybrook vacation home before booking.

How long can I rent a vacation rental in Old Saybrook for?

The length of time you can book a vacation rental in Old Saybrook varies according to the property. Just enter your selected travel dates to display a list of options offering extended stays. With lots of features such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to discover the perfect place to call your home away from home in Old Saybrook.

Does Vrbo offer discounts for vacation homes in Old Saybrook?

Weekend break or extended escape, Vrbo has some fantastic deals and discounts in Old Saybrook that’ll match your style and budget. Browse our weekly and monthly discounts on vacation rentals, or see what’s just been added with one of our newly listed homes. Whatever you’re after, you’ll find the perfect place to stay — without draining your wallet.