Discover a selection of 347 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 $121 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.
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Top rated rentals — Old Saybrook
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Destination guide

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, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Things to do

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:

  • Essex Steam Train (4 mi / 6.5 km)
  • Dinosaur Place at Nature's Art (12.3 mi / 19.9 km)
  • Kontokosta Winery (12.6 mi / 20.2 km)
  • Greenport Carousel (13.5 mi / 21.8 km)
  • Machimoodus State Park (14.7 mi / 23.7 km)
  • Sparkling Pointe (16.6 mi / 26.8 km)
Weather

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.

Natural features

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 (4.5 mi / 7.2 km)
  • Rocky Neck State Park (7.1 mi / 11.5 km)
  • Hammonasset Beach (9.4 mi / 15.1 km)
  • Gillette Castle State Park (9.4 mi / 15.1 km)
How to get there

How to get to and around Old Saybrook

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 26.8 mi (43.1 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to New London, CT (GON-Groton - New London), which is 17.3 mi (27.9 km) away.

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

What are the top vacation rentals in or near Old Saybrook?

Whether you're searching for a cozy escape for you and your honey or somewhere spacious to fit family and friends, you'll find some top vacation rentals in and around Old Saybrook. Here are a couple to get your inspiration flowing:

  • Around 20 miles from the center of Old Saybrook, it's hard to top "Classic Lake House With Private Waterfront". It has 3 bedrooms and a host of amenities including beach sun loungers and a smart TV.
  • "Beachfront Classic New England Home With Direct Views Of Long Island Sound" also promises a memorable getaway, offering 5 bedrooms, air conditioning, nearby birdwatching activities and more. It's around 2 miles from Old Saybrook.

For even more great options, use the search bar at the top of the page to find the perfect Old Saybrook vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Old Saybrook?

If you've been busier than an ant in a picnic basket, you deserve to get away for a few blissful days. Leave work early on Friday and make your way to one of these weekend getaways in or near Old Saybrook:

  • "Stunning Family Friendly Cottage Downtown Old Saybrook" is perfect for a few days of fun and relaxation. It features convenient amenities, such as an iron and ironing board and a garden, and is located around 0.1 miles to the southeast of Old Saybrook.
  • Alternatively, create memories with your loved ones at "Gorgeous Top Floor, High Ceiling And Brand New Apartment", which is around 0.1 miles to the northeast of Old Saybrook. Take advantage of nearby ecotour services, spa and beauty services and more here.

Can I find studio apartments for rent in and around Old Saybrook?

You certainly can. If you want a small but stylish stay, you can't beat a studio apartment. These compact properties ooze charm and are often conveniently placed in the middle of town. Take a look at the following options in or near Old Saybrook:

  • One of our favorite picks is "Marina Guest House". Lock in a few nights or longer at this popular stay and you'll have access to a stovetop and a hair dryer.
  • Another fantastic property is "Cottage At The Marina". Don't let its modest size fool you — this comfy apartment is packed with useful amenities like free WiFi, a hair dryer and much more.

Can I find short term rentals in or near Old Saybrook?

Whether you're in search of a cottage for you and a friend or a vacation home that'll fit the family, short-term rentals are easy to find in and around Old Saybrook. These properties make the perfect base for a quick trip:

  • Within easy reach of central Old Saybrook, "Downtown, Main Street, Center Of It All Location" welcomes short-term guests. When you're not holed up in your cozy digs, get out and discover all the fun stuff around you.
  • "Exhale At Old Saybrook's Chic Retreat" is also ideally located. Put your feet up here and find out why lots of guests rate this property highly.

What are the best romantic weekend getaways in or near Old Saybrook?

Nothing says "I love you" like a romantic weekend rendezvous. If you're longing to spend a couple of evenings away with your honey, we've got some romantic getaways in and around Old Saybrook that will set your heart aflutter:

  • Around 20 miles from Old Saybrook, "Classic Lake House With Private Waterfront" is the perfect place for starry-eyed couples. Winery tours and a fireplace are among the many amenities here.
  • "Beachfront Classic New England Home With Direct Views Of Long Island Sound" is another terrific option that'll impress. It's approximately 2 miles from Old Saybrook and has a fireplace and beauty services.

Are there mansions for rent in or near Old Saybrook?

Nothing says "best vacation ever" like staying in a mansion. Spoil the family with an unforgettable escape at one of these mansions for rent in or near Old Saybrook:

  • Located around 17 miles to the northwest of Old Saybrook, "Historic Mansion 1841" is the perfect place to relax in total luxury. Nice touches here include a firepit and a porch.
  • With a fireplace, golf and loads of other first-class amenities, "Magnificent Victorian Mansion On Bashan Lake Connecticut Direct Lakefront" will get your guests' tick of approval. This opulent home is roughly 14 miles to the north of Old Saybrook.

What are the best large group vacation rentals in or near Old Saybrook?

Peep these large group vacation rentals in or near Old Saybrook and don't worry about leaving anyone off your guest list:

  • Offering privacy, comfort and space, you'll get everyone's stamp of approval at "Beachfront Classic New England Home With Direct Views Of Long Island Sound". Up to 12 people can stay at this property which has 5 bedrooms, a nearby waterfront and a garden. This top pick is around 2 miles to the south of Old Saybrook.
  • "5 Bedroom Cottage Steps From The Beach @ Great Hammock Beach" is another terrific option. It's around 2 miles to the southwest of Old Saybrook, has 5 bedrooms and welcomes up to 12 guests. A water park and a kitchen are among the things that'll help make your group vacation more comfortable.

What are the best houses for rent with a pool in or near Old Saybrook?

A pool is often a nonnegotiable when choosing where to stay on vacation, particularly if you're traveling with kids. Check out these houses with a pool in or near Old Saybrook and fill your days with frolicking and fun:

  • Pack your swimsuit and book a few days or more at "A Saybrook Manor Vacation Beach House". There are also lots of other convenient amenities here, including childrens activities and a travel crib.
  • Spend lazy vacation days splashing around or just unwinding by the water at "Newly Renovated House - 5 Minute Walk To Private Beach". This vacation rental is another guest favorite and comes with a fridge, free toiletries and more.

Old Saybrook has an oceanic climate, with average summertime temperatures ranging from 65 ºF to 80 ºF. But there's no need to wait until summertime to visit. Check out the search bar at the top of the page and adjust the filters to find the perfect Old Saybrook vacation rental and plan your escape for whenever you like.

What are the best large family vacation rentals in or near Old Saybrook?

Grammy and Pop, Uncle Elijah ... You can add them to your invitation list when you choose a large family vacation rental in or near Old Saybrook. Get your nearest and dearest under the one roof at one of these spacious escapes:

  • Make your rendezvous an unforgettable one at "One Bedroom Apartment With Balcony And Sea View Maslenica". This escape has 3 bedrooms, caters to 10 guests and features lots of handy amenities, including a separate dining area and a living room. You'll find it around 20 miles north of Old Saybrook.
  • Also check out "Beachfront Classic New England Home With Direct Views Of Long Island Sound". It's about 2 miles to the south of Old Saybrook, has 5 bedrooms and accommodates up to 12 guests. Handy amenities here include a garden and a kitchen.

If you'd like to visit some family-friendly attractions close by, Stay and Play LLC promises a great day out for young and old.

Are there one-bedroom vacation rentals in or near Old Saybrook?

There sure are. You'll find a fabulous range of one-bedroom vacation rentals in or near Old Saybrook. If you only require a small space, one of these popular properties is sure to tick your boxes:

  • Book "Brand New Luxurious Cottage - Steps To The Beach" for a weekend. This one-bedroom vacation rental features a firepit and a garden and is close to the action of downtown.
  • Also within easy reach of all the delights of Old Saybrook, "Saybrook Point Cottage - Charming And Private" is another popular one-bedroom option. After a day of exploring, return and enjoy a kitchen and a nearby river.