Holiday rentals in Saybrook Point

Sunny Daze

This dreamy houseboat rests gently at a family-owned marina, where time seems to slow and nature leans in close. Surrounded by peaceful river views, tall grasses, and birdsong, it’s a floating haven for those seeking calm and creativity. Whether you’re sipping coffee on the deck at sunrise or watching the moon ripple across the water, this riverside retreat invites you to drift, dream, and just be. Enjoy a fire or jump on a paddle board or kayak f or an adventure down the river it has it all!

Osprey Cozy Cottage | Near Downtown & Beaches

Welcome to Osprey Cozy Cottage, a charming coastal retreat with beautiful views of South Cove in the heart of Old Saybrook. Just minutes from downtown, Saybrook Point, beaches, marinas, waterfront dining, and local shops, this inviting getaway is ideal for couples, solo travelers, business travelers, and weekend escapes. Enjoy picturesque South Cove views, explore Connecticut’s scenic shoreline, and discover the relaxed coastal charm that makes Old Saybrook a favorite destination year round.

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

The Saybrook Point Bungalow, Stroll to Downtown

Charming 2-bedroom cottage in Old Saybrook Point neighborhood, just a 1-mile sidewalk stroll to Main Street shops and restaurants. The primary bedroom features a king bed that can convert to two XL twins upon request, plus a second bedroom with a twin. A large couch can sleep a fourth guest. Enjoy warm, modern touches throughout, a Smart TV in the living room, a sunny back porch, and a quiet yard perfect for morning coffee or relaxing after a day exploring this beautiful beach town.

Beautiful View Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

Red Bird Waterfront Home. Dock available extra!

Looking for a stylish and spacious place to stay for your next group trip? Look no further than this waterfront home, perfect for families looking to relax and create lasting memories by the ocean. Interested in hosting an event? Ask us! This beautiful home offers stunning views of the water and plenty of space for your family to enjoy. Whether you're looking to spend your days lounging on the beach, exploring the nearby attractions, or simply relaxing with your loved ones.

Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace

Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

The Cottage

Step into a piece of history with this charming, fully converted 1930s changing house. Ideally located, it’s just a short stroll to downtown or a scenic bike ride to the beach, putting the best of the area right at your doorstep. Inside, you’ll discover a thoughtfully designed studio layout, offering the perfect setting for a peaceful getaway. The Cottage seamlessly blends comfort, convenience, and character, creating a truly inviting retreat.

The Connecticut Cottage | Historic Modern Charm

Welcome to The Connecticut Cottage — a beautifully restored 1790s stone cottage blending historic New England charm with modern comfort. Thoughtfully renovated from top to bottom, this one-of-a-kind home offers the perfect mix of cozy escape and central convenience along the Connecticut shoreline. Whether you're planning a laid-back coastal getaway or exploring some of New England’s most iconic destinations, you’re perfectly positioned!!

Luxury Driftwood Cottage @ Saybrook Point

The Driftwood Cottage is your next seaside getaway, with two King beds and a full and just steps away from the Saybrook Point Marina nestled between the Long Island Sound and Connecticut River. Whether you are docking for the weekend, attending a wedding, or need a romantic getaway. Enjoy the warmth and history of Historic Old Saybrook with our cozy cottage as home base. We love Connecticut and making ever-lasting memories for our guests!

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!