Beachfront holiday rentals in Madison

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

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!

The Rising Tide Cottage

The Rising Tide Cottage is recently updated and located in a quiet neighborhood on the Connecticut shoreline. Downtown Madison is less than a mile away and home to award-winning restaurants, a movie theater, and many shops. We are 5 houses down from our neighborhood Pent Road Beach and supply complimentary beach chairs, towels and umbrella. Enjoy your morning coffee on the private patio watching the tide rise and fall, overlooking a protected wildlife sanctuary at Hammonassett Beach State Park

A Beach House Gem

Beautiful beach cottage with a private beach. Sleeps up to 6 comfortably with two full beds and 1 queen in the master. with a beautiful balcony Full bath upstairs,1/2 off the kitchen entrance outside key on the key chain The main living area has a TV, air conditioning, and sliding doors to a deck. The updated kitchen has a dishwasher, microwave, cooktop, oven, and coffee maker. There are 2 parking spots in front of the garage The house is not winterized there are no bookings from Nov1

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.

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

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.