Holiday rentals in Madison

Newly Restored Cottage on River

Newly restored cottage, after being off Airbnb for 5 years, with cathedral living/kitchen area. Indoor/outdoor fireplaces & views of the stone sculpted grounds on the West River. The bedroom is on the ground floor with bath & wood stove. There are miles of trails across the river at Bittner Park. Bittner has a beautiful 18 hole disc golf course, pickle ball courts, basketball and a running track. A 1/4 mile away by car or a 5 minutes walk over the "Peter Pan Bridges"-not for the faint of heart.

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

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

Get Back to Nature at a Modern Wood Clad Getaway

HAPPY SPRING… PEEPERS are singing. The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Perfect Cape Beach Cottage in Madison CT!

Come enjoy your perfectly quintessential New England vacation in this beautiful beach cottage in Madison, Conncecticut - modern, luxe, and pull-at-your-heart-strings-endearing, your worries will melt away in this peaceful property. DEEDED BEACH ACCESS TO PRIVATE NEIGHBORHOOD SANDY BEACH - pics of the beach included. Note that bedrooms are located at the top of a (one-story) spiral staircase - if anyone in your party has mobility issues or questions on access, please contact host for inputs.

Riverfront Antique Cabin in the Heart of Madison

Antique, rustic cabin on Neck River just minutes from downtown Madison. Come kayak, birdwatch, and relax. First floor has a full, eat-in kitchen and tranquil living room with TV, pingpong, and games. Walk (1.5 miles) or kayak (during high tide) to Grass Island for a tranquil beach experience, or drive (2 miles) to downtown, with beaches, bookstores, a quaint town cinema and a wide array of restaurants. Relax (or fish) on the stone porch as egrets, osprey, and kingfishers fly above you.

Beach Sanctuary on the Long Island Sound

Kick back and relax in this stylish, retro, newly renovated coastal oasis with beach access & stunning views of the Long Island Sound. You can enjoy bird watching in the backyard garden in the spring, swimming and fishing at the private association beach in the summer, and leaf-peeping in the fall. The Beach Sanctuary is located in charming, historic Guilford CT, minutes from the town green, train station, local restaurants, and shopping as well as 20 minutes from New Haven and Yale.

Stylish Modern Home, 4-Bedroom, Madison CT

Beautiful 4-Bedroom Residential Home in Madison, Connecticut - Contemporary Scandinavian Interior Design - Close to Local/State Beaches (~10 Minute Drive) - Close to Local Parks and Hiking Areas (~3 Minute Drive) - Welcoming Open Floorplan - Quality Furnishings and Finishes - Up-to-Date/Modern Features/Clean and Comfortable - Wonderful Garden and Grass Lawn - Private (House Sits on 2-Acre Parcel) - Enclosed Outdoor Shower - Surrounded by Natural Beauty of the Countryside

The Barn by the Sound

Spend a weekend in The Barn: a modern designed free-standing building with guest studio apartment above, designed to look like a barn; the studio has views at tree level of a quiet, old neighborhood; one block from Long Island Sound; on a section of the historic old Boston Post Road. There is lots of natural light coming from a large window with a lovely view of a privet hedge on our property overlooking a park like property across the street.

Direct Shoreline Long Island Sound Waterfront

A quintessential New England cottage with views of the water from all rooms. Spectacular sunrises and sunsets, enchanting panorama views. A stone's throw from the beautiful Grass Island state park and boat launch, a waterfront natural preserve, perfect for hiking or communing with nature. The interior underwent a full renovation in 2020 with new appliances and bath fixtures. Original structure preserved. A tranquil, quiet place.

2 BR carriage house in Madison Center!

Escape to this sunny cottage just steps from the historic town green. Featuring vaulted ceilings and a light-soaked living area, this two story space offers a quiet backyard with a country feeling. Less than a 15 minute walk to the beach, 10 minutes from the train and a quaint New England downtown area complete with movie theater, restaurants, a world-famous bookstore and library, the location of this property is hard to beat.

Guilford Field House

Enjoy a wonderful guest house with all the amenities on a historic property in Guilford, Connecticut. The main house built in 1779 extends its character to the guest house which has views of an open field. On property there is a working restored horse barn. We are minutes to the spectacular downtown area of Guilford and easy access to Durham, Madison, and other surrounding towns and highways!