Old Saybrook Vacations
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Find the Best Old Saybrook Vacation Packages
Old Saybrook Beach Vacation
Shake off the stresses of daily life and let your body, mind and soul unwind on your Old Saybrook vacation. There's nothing more refreshing than the salty sea air and the sound of waves lapping at the shore. Plan your trip to Old Saybrook the easy way by choosing one of our Old Saybrook vacation deals. Many visitors choose to stay near Chalker Beach, a local highlight only 3 kilometers from the downtown area.
Things You Should Know About Old Saybrook
- Choose one of our Old Saybrook beach hotels to enjoy the very best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises right on your front door.
- Our private vacation homes, like Saybrook Point Resort & Marina and Super 8 by Wyndham Old Saybrook, are popular with travelers of all sorts. Check out the facilities and get set for your stay in Old Saybrook!
- Head to our Old Saybrook things to do page for some trip planning inspiration. With a population of roughly 10,600 inches Old Saybrook, we're sure there'll be a few locals who'll be pleased to give you some extra advice!
- If you're searching for things to do while you're in town, add Hammonasset Beach State Park, Hammonasset Beach State Park and Clinton Crossing Premium Outlets to your travel itinerary. Also, take a look at our Old Saybrook vacation deals to get great deals on your hotels and experiences.
Old Saybrook Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
NT$2,595
NT$2,984 total
Sep 23 - Sep 24
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Staff was helpful and professional. Room was clean, basic, nice. The TV was a little sketchy-some stations were static. The bathroom shower was great: good flow, hot and soothing. Overall, very good for the price."
Reviewed on 2026/9/17
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Fully refundableReserve now, pay when you stay
NT$11,100
NT$13,879 total
Oct 4 - Oct 5
includes taxes & fees
Two Trees Inn
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
NT$2,954
NT$3,397 total
Sep 21 - Sep 22
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Old Saybrook attractions
Harvey's Beach
8.8/10 (93 reviews)
Harvey's Beach offers pristine white sand and calm, shallow waters perfect for families with young children. Explore the expansive sandbars at low tide to discover fascinating tide pools and marine treasures.
Chalker Beach
8.8/10 (26 reviews)
This private Connecticut shoreline offers a tranquil escape with soft sands and gentle waves. Generations of families have created a close-knit beach community here since 1931, complete with summer concerts and bonfires.
Katharine Hepburn Cultural Arts Center
8.8/10 (53 reviews)
The Kate honors Katharine Hepburn's legacy through intimate performances in Old Saybrook. Enjoy theater productions, then explore the museum's collection of the iconic actress's costumes and memorabilia.
Essex Saybrook Antique Village Shopping Center
9.0/10 (66 reviews)
Discover treasures spanning decades at this 6,000-square-foot antique haven with over 50 dealers. Browse art glass, nautical artifacts, and vintage furniture while knowledgeable staff share the stories behind each piece.
Crystal Lake Town Park
8.4/10 (16 reviews)
This 180-acre recreational haven features trails, sports fields, and Crystal Lake for fishing. Hike through scenic woodlands or gather with family at the pavilion overlooking tranquil waters.
Saybrook Country Barn
9.0/10 (27 reviews)
Housed in a historic 1799 building, Saybrook Home offers 42,000 square feet of premium furniture and designer apparel. Browse multiple showrooms of quality home décor before dining at the on-site Aspen Restaurant.
General William Hart House
9.0/10 (17 reviews)
Step into the 1767 Georgian residence of Revolutionary War General William Hart, with its distinctive eight corner fireplaces. Guided tours reveal colonial life through period furnishings and family stories.
Fort Saybrook Monument Park
10.0/10 (1 review)
Explore Connecticut's first military fortification from 1635 at this historic waterfront park. Follow the elevated boardwalk for panoramic river views and discover colonial history through informative storyboards.
