Holiday rentals in Old Saybrook

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Top-rated holiday rentals in Old Saybrook

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Top guest favourite

Home in Old Saybrook

5 out of 5 average rating, 51 reviews

3BR Updated Cottage w/ Pool in Old Saybrook

Welcome to Osprey Lookout! 3 bedroom, 1 full bath updated cottage located in the quintessential New England beach town of Old Saybrook, CT. With distant views of Long Island Sound from the pool deck, this single-family cottage in a private setting has everything you need to enjoy a relaxing family vacation, including an outdoor shower to rinse off after a day at the beach! Nearby: - Harvey's Beach - Connecticut Wine Trail - Essex Steam Train - Mohegan Sun & Foxwoods - Historic Mystic Seaport

Guest favourite

Guest suite in Old Lyme

4.89 out of 5 average rating, 270 reviews

Luxurious Old Lyme King Bedroom Suite

First floor king bedroom suite in Ludington House, a historic home centrally located in the charming village of Old Lyme. Perfect for couples. Luxuriously appointed with California King bed, spacious kitchenette, bathroom and separate entrance. Private porch with view. Close to restaurants, beaches, art galleries and museum. Located in stunning historic mansion (location of film "Christmas at Pemberley Manor" 2018). Sorry - no pets, it will not work with our own pets. Guests must be 21 plus.

Superhost

Cottage in Westbrook

4.88 out of 5 average rating, 165 reviews

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.

Guest favourite

Cottage in Old Saybrook Center

4.91 out of 5 average rating, 11 reviews

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.

Top guest favourite

Guest house in Portland

5 out of 5 average rating, 221 reviews

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

Top guest favourite

Cottage in Old Saybrook Center

4.98 out of 5 average rating, 125 reviews

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.

Top guest favourite

Home in Lyme

4.98 out of 5 average rating, 276 reviews

“The Answer” Your Unique, Tidal, Riverfront Escape

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil tidal water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

Top guest favourite

Cottage in Old Saybrook Center

4.97 out of 5 average rating, 79 reviews

1920’s charming dollhouse near South Cove

Simple, no frills guest cottage near South Cove in Old Saybrook. Drop your kayak /paddle board in at the end of the street, walk to town for dinner or a show at the Katherine Hepburn Theater, or enjoy a day at town beach only 1.5 miles away. This is a shabby chic escape in a friendly, quiet neighborhood. A few quirks but tons of charm! If you are looking to unplug and sit by the fire pit, read a book, and go to the beach, this is the place for you.

Guest favourite

Home in Old Saybrook Center

4.72 out of 5 average rating, 226 reviews

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.

Guest favourite

Barn in Essex

4.96 out of 5 average rating, 160 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Top guest favourite

Guest suite in Westbrook

4.96 out of 5 average rating, 78 reviews

King Bed, Walk to Beach, Kitchenette, Porch/Patio

Discover why guests are raving about our private guest suite in coastal Westbrook, CT! Thoughtfully designed for comfort and convenience, it’s an ideal retreat for those seeking a seamless, relaxing travel experience. Perfect for solo travelers or couples, the suite combines contemporary design with thoughtful amenities for an unforgettable stay. Guests love the proximity to the beach, fine dining, and local attractions!

Guest favourite

Tiny home in East Lyme

5 out of 5 average rating, 138 reviews

Luxury Tiny Home Near Rocky Neck

Home away from home at our chic hideaway! Create a culinary masterpiece in the fully-appointed kitchen. Pamper yourself with heated floors in the bathroom, outdoor fire pit and heater. An elevated platform perfect for camping or yoga. Nestled just minutes from the picturesque Rocky Neck and McCooks beach, this is the ultimate small family romantic retreat or solo experience!