Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.
Old Saybrook Information
About Old Saybrook Old Saybrook in Middlesex County, Connecticut is one of the oldest towns in the state. It has a rich history that dates all the way back to 1624. The settlement was once a trading post for Dutch settlers. Then it became an independent colony known as the Saybrook Plantation. A few decades later, Yale University—then called the Collegiate School—was founded in town. Now, Old Saybrook is a community of more than 10,000 residents. The town includes the borough of Fenwick as well as two census-designated places. Conveniently located where the Connecticut River meets the Sound, Old Saybrook has been a consistently sought-after destination of days past and present.
Things to do in Old Saybrook Main Street is the heart of Old Saybrook. It has over 375 years of history to boast of, and is attractive on many fronts. Quaint eateries and storefronts line the boulevards. Specialty shops and independent businesses offer quality goods and unique products. Local merchants are friendly and knowledgeable in their craft. They might even let you in on the yearly “Strolls” that happen on Main Street twice a year. Ask them about the annual Chilifest and Art Show, and the weekly Concerts on the Green held Wednesdays throughout the summer. Old Saybrook also has two public beaches for recreation. Harvey’s Beach and Saybrook Point are popular destinations for swimming and boating. Several companies offer fishing excursions and cruises in the Sound. You might catch a glimpse of Lynde Point Lighthouse or Saybrook Breakwater Lighthouse while at sea. These are noted attractions on the National Register of Historic Places. Other listings from town include Black Horse Tavern, William Tully House and the Connecticut Valley Railroad and Turntable Site.
Day trips from Old Saybrook Old Saybrook isn’t too far from its neighbor states. It’s convenient to take Amtrak into major cities like Boston or New York. From Old Saybrook, it’s about 127 miles, or 2.5 hours to Boston, Massachusetts. Where Old Saybrook is consistently old-town charm, Boston’s a smorgasbord of the old and the new. The Boston Harbor and Paul Revere House are carefully preserved remnants of the past. Then there’s the Museum of Science and Fenway Park, manifestations of progress and achievements. Mesh the best of past and present, and you get attractions like Faneuil Hall and Newbury Street. Modern times meets historic architecture in this marketplace and shopping district. For an entirely different experience from Old Saybrook, take a day trip to the Big Apple. New York City is 110 miles southwest of Old Saybrook. NYC is where you’ll find endless crowds, unparalleled diversity and controlled chaos. If you want to see where Yale University makes its new home, check out the town of New Haven. It’s just 30 miles due west. You’ll find a number of Yale-centric attractions befitting of the third oldest institution of higher education in the United States. The area also has a lively arts and culture scene due to its theaters and performance halls.
Old Saybrook accommodations As with many quaint beachside towns, Old Saybrook has its share of quaint cottages and charming B&Bs. However, those aren’t your only options. The town has guesthouses for rent for those who prefer a homier atmosphere. There are also resorts and spas for a more comfort-centric experience. The motels and inns in town offer great price range in terms of affordability.
Transportation in Old Saybrook Amtrak is a great way to get in and out of Old Saybrook. It runs along the Northeast Corridor with daily service to Boston, New York and areas further south. There’s also regular commuter service to New Haven and Stamford. You can take the Shore Line East, courtesy of the Connecticut Department of Transportation. If you’re trying to get around town, the Estuary Transit District is the main transportation provider to Old Saybrook and surrounding areas. It’s easy to explore the region on foot or by bike once you get into town. If you decide to drive into Old Saybrook, Connecticut Route 154 is one of the main thoroughfares through town.
Vacation Rentals in Old Saybrook Looking for the perfect vacation rental for your Old Saybrook getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Old Saybrook offers 43 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 36 properties with high-speed WiFi Internet, 0 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget. For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $25 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Old Saybrook has 43 gorgeous homes with 8 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com. Search properties from 5 vacation rental sites in Old Saybrook where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 27 HomeAway rentals, 6 Booking.com short term rentals and 4 TripAdvisor vacation rentals.