Beach house holiday rentals in Old Saybrook

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Top-rated beach house rentals in Old Saybrook

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Guest favourite

Home in Groton

4.95 out of 5 average rating, 208 reviews

True Ocean Front Vacationing - Groton/Mystic

Bright and airy contemporary beach house with breathtaking views of Long Island Sound. Conveniently located just 15 mins to Mystic/Stonington; 23 to Foxwoods/Mohegan Sun . Relax on the lower deck and drop a fishing line in the ocean as it greets the seawall at high tide. Or retreat to a private roof deck to enjoy your favorite beverage as you take in the most romantic time of the day, the golden hour featuring beautiful sunsets. Parking for 3-4 cars. We hope you enjoy this escape by the sea!

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Home in East Haven

4.89 out of 5 average rating, 236 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

Top guest favourite

Home in New Haven

4.95 out of 5 average rating, 122 reviews

Beach Haven - waterfront, near Yale, sunsets

Everything you need for an amazing vacation, year-round, in our comfortable home right on the beach! Walk out the back door and dip your toes in the sand and in Long Island Sound. Enjoy spectacular views from the back patio, sun room, and most rooms in the house. Watch the sunset while soaking in the hot tub. Sit by the gas fireplace with a book. Stroll along the lovely nearby sea wall. 10-minute drive to Yale and all downtown New Haven has to offer. 5-minute drive to Lighthouse Point Park.

Guest favourite

Home in Milford

4.96 out of 5 average rating, 238 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Guest favourite

Home in East Lyme

4.96 out of 5 average rating, 196 reviews

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.

Top guest favourite

Home in Eastford

4.93 out of 5 average rating, 111 reviews

Serenity Ashford Lake

Peaceful and charming country lakefront home with a hot tub! Welcome to Serenity Ashford Lake. This lake home is removed from the everyday hustle and bustle of life. Nestled on the shores of beautiful Ashford lake, your stay is bound to create lasting memories. Plush furniture, central air, stainless steel appliances, cozy linens, washer/dryer, kayaks and a canoe, paddleboat, firepit, boutique toiletries and a new kitchen space make up this beautiful lake home. Bring your book and enjoy!

Top guest favourite

Home in Branford

4.98 out of 5 average rating, 179 reviews

“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!

Top guest favourite

Home in Waterford

4.98 out of 5 average rating, 120 reviews

Niantic River Beach Cottage | Waterviews

Kick back and relax in this quiet, peaceful, and stylish space! Enjoy the water views, private beach, outdoor shower, powerful heat/AC, and beautiful patio. Beaches, coffee shops, bakeries, local ice cream stands, seafood, local shops, boat launches, outdoor music venues, top rated restaurants, hiking, and more! This quintessential New England cottage gives easy access to the best of South Eastern Connecticut. Check out the reviews to see why guests love visiting this beach cottage!

Guest favourite

Home in Southampton

4.98 out of 5 average rating, 103 reviews

Breezy Waterfront Home With private Dock

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

Guest favourite

Home in Montville

4.9 out of 5 average rating, 151 reviews

Thames River Cottage · Near Casinos + USCGA

4 MILES from MOHEGAN SUN! FREE EV LVL-2 Charging! Come relax at the cottage on the Thames River w/ direct river view and access, free Kayaks on site for use, spacious patio, firepit, gas grill, privet boat launch/dock. 10 min from CT College & USCGA, 20-25 min drive to Foxwoods, Mystic, Stonington, Vineyards, local breweries, New London Navy Base, Pfizer, GD (EB) & Mitchell. Cottage is located at the end of Point Breeze (Horton Cove side) with direct river access.

Guest favourite

Home in Montauk

4.98 out of 5 average rating, 100 reviews

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts

Guest favourite

Home in East Lyme

4.93 out of 5 average rating, 156 reviews

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC

INSTANT BOOK: Sept '25 - Jan New Year '26 All Open Availability SUMMER '26: End June + July + Aug Now Available for Instant Booking Amazing Views - Waterfront Both Balcony (year round) & Boardwalk Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discount applied to nightly rate only *we can not combine multiple discounts, yet highest % applies *if available, apply 10% non-refundable booking option