
Beachfront holiday rental in Old Saybrook
Find and book unique beachfront homes on Airbnb
Top-rated beachfront accommodation in Old Saybrook
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

Niantic River Beach Cottage | Waterviews
Kick back and relax in this quiet, stylish New England beach cottage with water views, a private neighborhood beach, an outdoor shower, and a sunny patio for coffee or evening wine. Just minutes from downtown Niantic, you’ll find beaches, cafés, bakeries, ice-cream stands, seafood, boutiques, boat launches, trails, outdoor concerts, and more—all within a short drive or bike ride. Perfect for a romantic getaway, a family weekend, or some quiet coastal downtime. See why guests love staying here!

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!

Beachside Waterview 2Br Condo w/ Pool in Greenport
Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

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!

Beachfront Paradise
Beautiful beachfront home available weekly in season (6/20/26-9/5/26) 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.

Savor Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

“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!

Updated cottage "Beriozka" on Cedar Lake
Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Waterfront Joshua Cove Cottage with private beach.
Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

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,

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.

Brand New Direct Lakefront - Panoramic Sunsets
Completely remodeled lakefront apartment with stunning views of Pattagansett Lake. Guests love the peaceful setting, spacious layout, and large deck overlooking the water—perfect for relaxing or gathering with family and friends. Spotlessly clean with comfortable queen memory-foam beds, fresh linens, UHD smart TVs, fast Wi-Fi, and in-unit laundry. Quiet, private, and scenic, yet minutes to beaches, restaurants, casinos, and area attractions.
Popular amenities for Old Saybrook beachfront rentals
Pet-friendly beachfront home rentals

Beachfront house on Long Island Sound

Private beach, fully updated house, on 2 acres.

Eastern Point 4 Season Ranch

Charming Fairfield Beach Cottage

Waterfront Bungalow w/Private Beach on Peconic Bay

Coastal getaway with water views in every room

Hang by the (Chel)SEA

The North Star: Greenport Waterview Beach Getaway
Beachfront home rentals with a pool

NoFo Getaway: Pool, Farm Views, Beach Sunsets

Beautiful Waterview Condo on the North Fork of LI

Coastal Escape w/ Pool - Near Niantic & Beaches

Condo on the ocean in Montauk

North Fork Sound Front Home with Pool

3BR Adirondack Guest House on 36 Acre waterfront

Charming East Hampton Home, Private Heated Pool

Pine Creek Beach House
Private beachfront home rentals

MAGNIFICENT PRIVATE RIVERFRONT HOME, 10% off

Scenic Mulberry Point Connecticut Beach House

Waterfront Beach Cottage in Connecticut

Large Waterfront Cottage on Historic Estate

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

Beach Home with View

Incredible 2 Bedroom Waterfront Cottage!

Cheerful 3 Bedroom Cottage with Fire Place
Quick stats about beachfront rentals in Old Saybrook

Total holiday rentals
Explore 20 holiday rentals in Old Saybrook

Nightly prices starting at
Old Saybrook holiday rentals start at $343 NZD per night before taxes and fees

Verified guest reviews
Over 570 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
20 of Old Saybrook holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Old Saybrook rentals

4.9 Average rating
Old Saybrook stays are highly rated by guests—averaging 4.9 out of 5!
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- House rentals Old Saybrook
- Rentals with beach access Old Saybrook
- Rentals with a patio Old Saybrook
- Rentals with outdoor seating Old Saybrook
- Cottage rentals Old Saybrook
- Waterfront rentals Old Saybrook
- Family-friendly rentals Old Saybrook
- Beachfront rentals Connecticut
- Beachfront rentals United States
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Ocean Beach Park
- East Matunuck State Beach
- Mohegan Sun
- Hammonasset Beach State Park
- Long Island Aquarium
- Mystic Seaport Museum
- Powder Ridge Mountain Park & Resort
- Mount Southington Ski Area
- Yale University Art Gallery
- Sleeping Giant State Park
- Point Judith Lighthouse
- Burlingame State Park
- Ski Sundown
- Orient Beach State Park
- Ocean Beach
- East Hampton Main Beach
- Mystic Aquarium
- Meschutt Beach




