Beach house holiday rentals in Old Saybrook

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

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Beachfront Paradise

Beautiful beachfront home available weekly in season (6/21/25-9/6/25) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, movie theatre, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Stunning Waterfront Cottage with Big Yard & Dock!

Escape to the tranquil beauty of "A Summer Place," a charming 1,500 sq ft waterfront cottage nestled just steps from RI's stunning coastline and pristine beaches. Whether you're planning a family getaway or a retreat with friends, this idyllic home offers the perfect blend of rural charm and modern amenities, all in a prime location near local shops, bakeries, cafes, and top-rated restaurants. The expansive yard and private dock provide an unbeatable setting while you sit back and relax!

“The Lighthouse” A Beach Cottage by the Sea!

Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

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

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

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.