Holiday rentals in Saybrook Point

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Value · Location · Accuracy

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!

Family · Location · Air conditioning

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Location · Family · Getting around

Serene Coastal Cottage steps from South Cove

Welcome to your perfect private seaside escape! Nestled in the heart of Old Saybrook, this cozy 1-bedroom cottage blends classic New England charm with modern comfort. Just a short stroll from the beach and historic downtown, this cottage is ideal for a relaxing getaway or a romantic retreat. Wake up to salty sea breezes and enjoy your morning coffee on the deck. Whether you're exploring the nearby attractions, dining at local restaurants, or unwinding with a book, you’ll feel right at home.

Location · Family · Sleep quality

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.

Location · Cleanliness · Quiet

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.

Location · Family · Accuracy

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.

Value · Family · Heating

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.

Location · Family · Indoor spaces

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.

Location · Family · Parking

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!

Family · Location · Parks

Best of both worlds!

Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!

Family · Location · Sleep quality

Your Nest Near The Beach

Welcome to A Shore Thing, a retro modern beach cottage. This bright and cheerful escape is perfectly located for exploring the shoreline. Whether you are visiting in the summer for sun, surf and sand or in the quieter off-season, you will find the shoreline is packed with an incredible array of inviting destinations. The cottage is just 3/4 of a mile from the beautiful private sandy beach.

Family · Value · Condition