Beach house holiday rentals in Madison

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Top-rated beach house rentals in Madison

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Guest favourite

A spacious lawn leads to a charming beachfront cottage, surrounded by lush greenery and large boulders. The structure features multiple windows and a sunroom, blending with the natural setting. A deck area is visible, inviting outdoor relaxation and enjoyment of the peaceful surroundings.

Home in Guilford

4.95 out of 5 average rating, 79 reviews

Scenic Mulberry Point Connecticut Beach House

Waterfront beach cottage in a peaceful setting with spectacular unobstructed views of Indian Cove, Faulkners Lighthouse, Osprey Nests and beyond! You won’t find a more wonderful place for your vacation. This lovely two bedroom home with sunroom and deck is perched above the ocean and directly fronts the beach to provide the ideal relaxing retreat. No matter which time of year you visit, you will appreciate the tranquility of the ocean and feel completely relaxed and at home during your stay.

Top Guest favourite

An expansive wooden deck features a circular picnic table with attached benches, overlooking coastal views. The area is bordered by a railing, and additional seating options are visible. A clear sky and soft clouds provide a serene backdrop.

Home in Milford

4.94 out of 5 average rating, 143 reviews

#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!

Top Guest favourite

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in Springs

4.95 out of 5 average rating, 252 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.

Top Guest favourite

A charming cottage is depicted with a shingle exterior, a welcoming front porch, and a chimney. The grassy landscape is flanked by flowering shrubs, and a path leads to the entrance. A red barn is visible in the background, enhancing the rural setting.

Home in Waterford

4.99 out of 5 average rating, 142 reviews

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!

Guest favourite

A wide view of Long Island Sound is captured from a private deck, featuring tranquil water and distant boats on the horizon. A white railing frames the scene, while greenery and a flagpole are visible in the foreground, indicating a peaceful outdoor setting.

Home in Guilford

4.88 out of 5 average rating, 17 reviews

Picturesque Waterfront Villa

Spectacular location! Bring your whole family to a dream spot right on the water! Enjoy the best view from the open kitchen + living room. Don’t forget about the deck. Stocked kitchen with everything you could need. Entertain yourself with large flat screen TVs and Roku streaming devices. The king bedroom faces the water with an extra wide window. A yard for the kiddos. Take the steps down to the bay. We have beach towels for you. Plenty of parking. Serious wifi. You may not want to leave.

Guest favourite

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.97 out of 5 average rating, 260 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!

Top Guest favourite

A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.

Home in Niantic

4.97 out of 5 average rating, 217 reviews

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.

Guest favourite

A bright living area features large windows offering views of the ocean. A comfortable sofa draped with a soft blanket faces the water. Decorative accents include a small woven table, colorful rugs, and light-colored furniture, creating an inviting space filled with natural light.

Home in Old Lyme

5 out of 5 average rating, 51 reviews

Beachfront Oasis

Named in "thrillist.com" (7/6/22) "Best Beach Houses to Escape to Near NYC". This beachfront oasis is just steps from the beach with SUPs, kayaks, grill and more. Every comfort of home plus many luxury details including a Sub Zero chef kitchen and jet massage shower. Located in family friendly Hawks Nest Beach, Old Lyme, close to restaurants, shopping, casinos and the historic sights along the CT shoreline. Convenient, by car or train, to NYC and by ferry to Long Island and Block Island.

Top Guest favourite

An open-concept kitchen and living space features modern appliances and a wood-topped island with seating for three. Light cabinets and blue walls create a bright environment, while a hallway visible in the background leads to the entrance of the cottage.

Home in Branford

4.98 out of 5 average rating, 231 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

A bright living area features large windows that overlook the ocean, allowing natural light to fill the space. The room is furnished with a blue sofa, two armchairs, and a coffee table. A small plant adds a touch of greenery, and a dining area is visible in the background.

Home in Clinton

5 out of 5 average rating, 37 reviews

Soundscape Beachfront House!

Need an escape by the sea with gorgeous sunrises and stunning sunsets? Come stay at this beautiful beachfront retreat. Wake up with the best views of the Long Island Sound, smell the ocean and enjoy your coffee or wine while watching sailboats and admiring seagulls take flight. Sunbathe on the extended sand deck or step down into the lower sandy beach to swim, kayak, or paddle board. Come relax with friends and family, seize the day, escape the daily grind and get re-energized!

Top Guest favourite

A dining set featuring a large wooden table with eight matching chairs is positioned under a spacious umbrella, offering shade. Lush greenery and a serene waterfront view are visible nearby, providing a peaceful outdoor setting.

Home in Southampton

4.98 out of 5 average rating, 105 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

The living area features a large sectional sofa with a throw pillow, a dark coffee table, and a dining area with a wood table. Sliding glass doors open to a scenic view of the Thames River and the outdoor deck.

Home in Montville

4.89 out of 5 average rating, 188 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.