Beach house holiday rentals in Madison

4.95 out of 5 average rating, 237 reviews

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

5 out of 5 average rating, 9 reviews

Home in Milford

Salty Kisses Cottage Relax

Salty kisses beach cottage is simply adorable. The perfect getaway. Your happy place, always fresh linens, tasteful coastal decor. Direct water views Beach access across street Amazing sunrise and sunsets. At the end of the road is Silver Sands State Park with showers and food. Walk on the boardwalk to Walnut Beach. Live music, milford creamery, bees knees, pizza, lazy lobster and specialty stores. We have a lovely backyard for grilling and chillin. Downtown & Lisman landing only 1-2 mile walk.

Home in New London

New place to stay

Charming New London Beach House

*NEW* Coastal Charm Near Ocean Beach Charming 3-bedroom beach retreat just 3 minutes from the waves at Ocean Beach! Unwind in a bright, inviting space with plenty of room to relax. The spacious back deck is perfect for sunny breakfasts, evening BBQs, or stargazing under the coastal sky. Ideal for families, couples, or friends looking for a laid-back getaway. Fast Wi-Fi, TV, and 2 Roku’s included, your perfect beach escape starts here! Harkness Memorial State Park is also a close drive away!

5 out of 5 average rating, 22 reviews

Family Friendly Designer 3bd Centrally Located

Enjoy Montauk for all its pleasures and call this immaculate golf course house your home. Nestled on quiet Fairlawn Drive, you will enjoy a short walk to town, the train station, or the beach. The Manor is just down the street. Take a stroll up to the Fort Hill Cemetery for spectacular sunset views over Fort Pond Bay. If you plan to bring a bike, everything is within biking distance, and plenty is within walking distance. The golf course is just across the street. Rental Registry # 22-953

New place to stay

Designer’s home in Sag Harbor

Nestled in Sag Harbor, this elegant 5-bedroom home offers a saltwater heated pool just 2 miles away from the town. A mere five-minute stroll takes you to the Serene Green local farm stand and Long Beach Bay, where you can indulge in swimming, paddleboarding, and witnessing breathtaking sunsets. The chef's kitchen is perfect for culinary adventures, and you can savor your meals either poolside under the charming string lights at the 8-person farm table or indoors at the 8-person table

4.91 out of 5 average rating, 33 reviews

Home in Niantic

Bella’s Beach Cottage

NEW! Great amenities and beach location. Family friendly rustic 1950’s beach cottage in a private beach community, in Niantic, CT. Beach parking pass included, walk and/or park steps away from our private beach & walk into Rocky Neck State Park. A short drive to great restaurants, The Niantic Boardwalk, Foxwoods and Mohegan Casinos, shopping (Niantic, Westbrook Outlets, Clinton Crossing), Mystic Aquarium and Seaport, Garde Arts Center, The Kate & Niantic Children's Museum.

Newly Renovated Sag Harbor House

Welcome to this newly renovated, charming Sag Harbor house, just a short stroll from the beach and a delightful farm stand. This beautifully decorated home features a cozy yet stylish interior, perfect for relaxation and entertaining. The incredible backyard is a true oasis, adorned with designer landscape and luxurious and comfortable outdoor furniture. Enjoy sunny afternoons by the salt water pool or the fire pit in the evening. This idyllic retreat is the ultimate getaway!

4.91 out of 5 average rating, 11 reviews

Home in West Haven

Spacious 2BR Near Beach & Yale – Prime Location!

Unwind in this spacious and tranquil retreat, just steps from the beach in West Haven. This inviting 2BR home offers the perfect escape, blending comfort and convenience for a relaxing stay. Enjoy a bright, cozy atmosphere with modern amenities, ideal for families, couples, or business travelers. Whether you're exploring Yale, strolling the shoreline, or simply unwinding, this home-away-from-home ensures a stress-free getaway. Book now for a refreshing stay!

4.95 out of 5 average rating, 20 reviews

Beach Cottage | Steps to Water| Fireplace|Firepit

Kick back and relax in this calm, stylish beach cottage in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, firepit/BBQ area, and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in August/September/October stays).

5 out of 5 average rating, 29 reviews

Home in Guilford

Charming 2BR Beach House, Overlooking the Water

Relax and enjoy your time at this unique and tranquil getaway. Steps to the beach and a short drive to town. Wake up on the water with beautiful sunrise views. Recently renovated with new bathroom, new floors and freshly painted throughout. 5 minutes to local shops and restaurants in Guilford's charming town center, and easy access to several shoreline attractions nearby... Wineries, museums, craft breweries, kayaking and hiking.