Holiday rentals in Old Saybrook

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.

Her tiny Parisian boat house

Solo vacation? Reconnect with nature at this unforgettable escape. Or a Perfect work space while lounging by the pool…(in SEASON) this tiny house (on land) has access to an outdoor shower and outdoor soaking tub. Wanna relax? Come Meditate under the giant willow, swing in the hammock or practice yoga. Bathroom (NOT IN THE TINY HOUSE!) is shared and just steps inside the main house with shower and toilet. Great WiFi, front porch to enjoy meals. Bed is a comfytwin with lots of pillows.

Cornfield Point Beach House View

Nestled amidst marsh & water views, this beach house offers a relaxing coastal experience. Just a 10 min walk to the private family friendly Cornfield Point Beach. Enjoy beautiful sunsets from the house or during a leisurely beachside stroll, these panoramic views are sure to leave a lasting impression. The beach house is setup for relaxation-a fully equipped kitchen, cozy living areas & inviting bedrooms with new comfy mattresses and fluffy towels. Quick drive or bike to Main st.

Romantic Couples Retreat with Private Sandy Beach

Get ready to relax and unwind! Old Sea Lane Cottage is located in a peaceful quiet setting in Old Saybrook’s premier Indian Town Association. Tucked away on a dead end street, this cottage is home to your own private beach. Catch the sunrise and sunsets. During low tide, swim or paddle board across the water to Harveys Beach. You will never get tired of watching the birds and hearing the sounds of nature! This is a truly special location. INQUIRE ABOUT OUR EVENT FEE. No pets

“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.

Coastal Cottage Private Studio

Beautiful coastal studio cottage located on the shoreline of CT. Your cottage is spacious and private with keyless entry and private dedicated parking. Originally an art studio, this recently renovated cottage is one mile to the beaches and local attractions. Our cottage is popular among Connecticut College, Coast Guard Alumni/parents and for anniversary celebrations! Enjoy...Now you can kick back and relax... you've found your home away from home! 🤩🏡 😊

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.

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!

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.