Holiday houses in Madison

4.99 out of 5 average rating, 497 reviews

Guesthouse in Guilford

Get Back to Nature at a Modern Wood Clad Getaway

SPRING IS HERE--Glorious spring birds. Come and enjoy a wonderful time in our guest house--warm days, cool nights. You can Hike on the trails, and Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

4.88 out of 5 average rating, 163 reviews

Cottage in Westbrook

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

4.95 out of 5 average rating, 38 reviews

Guesthouse in Clinton

Studio Cottage

Peaceful & centrally located studio cottage on Connecticut shoreline. Close to beaches, restaurants, winery, outlet shopping, and I-95. Approximately 20 minutes outside of New Haven. Ideal for exploring the shoreline & river valley. Bright, clean, efficient, well- equipped cozy studio cottage with queen bed, sitting area, kitchen & full bathroom . Outdoor space with fire pit & grill. Onsite parking. Ideal for two people whether traveling through the area or for a little rest & relaxation

5 out of 5 average rating, 54 reviews

Guesthouse in Madison

Coastal River Barn Retreat

Spend your days in this newly renovated Coastal Barn Retreat, (which is immediately adjacent to our house). With a modern design and large windows, enjoy views of Neck River. Kayak down river to the Sound at high tide or bike to nearby local beaches with bikes (2) and kayaks (4) provided by owner. Close to town beaches, Hammonasset, Vineyards, Hiking trails. Tons of natural light. Living area is under a cathedral ceiling with forced air heat, air conditioning, and wireless wifi.

4.94 out of 5 average rating, 144 reviews

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views of River. Convenient to beaches, and includes free pass to the Clinton Town Beach! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to groceries, coffee shops and amazing CT scenery! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants with music, and lots more.

4.97 out of 5 average rating, 193 reviews

Waterside Beach Retreat

Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

4.8 out of 5 average rating, 15 reviews

Guest suite in Madison

Vintage Cabin Suite near Hammonasset Beach (No.1)

Cozy cabin suite near the beach and greenway trail, just a quick drive to charming downtown area. Cottage (#1) is a suite-style space including one bedroom with 1 queen bed; sitting room; coffee bar with coffee maker, mini fridge, microwave, and toaster; and, a small private bathroom with shower. This space can accommodate up to 2 adults. This building is a duplex and you may have neighbors in the adjacent suite. Each unit has a private entrance on opposite ends of the building.

4.89 out of 5 average rating, 18 reviews

Boulder Lake House Retreat

Experience the beauty of spring at our charming lake house—an ideal retreat for families, friends, or a romantic getaway! Nestled along Boulder Lake and just under 3 miles from Hammonasset State Park, our home offers the perfect mix of comfort and outdoor adventure. Wake up to the sight of the sparkling lake, sip your morning coffee on the deck, and soak in the fresh spring air! Spend your days fishing, exploring nearby trails, or dining outdoors as the season comes to life!

5 out of 5 average rating, 28 reviews

Home in Madison

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

4.93 out of 5 average rating, 61 reviews

Loft in Killingworth

A Peaceful Perch

Rustic, Restful and away from activity but under 10 minutes to the shoreline. You may find this over the garage studio the perfect place to perch for a weekend or a week. A short drive to the charming little town of Madison with many good restaurants and shops and to Hammonasset State park with walking trails and a beautiful beach . 48 River Rd. Is situated on the edge of a glacial rock formation on a scenic country road and is accessible to all the Good Stuff.

4.94 out of 5 average rating, 232 reviews

Guesthouse in Clinton

The Gardener's Cottage Dog friendly/weekly/monthly

The Gardener's Cottage, less then a mile from the Long Island Sound, is a great alternative to the common hotel. Situated a stones throw from Hammonasset State Park and Beach, Clinton Outlets, and the Shore Line East train station. Near by you will find places to kayak, Chamard Wineries, Marinas and many quaint New England towns. The Cottage is fitted with it's own router coupled with an eating nook that can double as a work space. Pets are allowed. Self check-in

4.97 out of 5 average rating, 77 reviews

Guesthouse in Madison

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.

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Popular amenities for Madison holiday rentals

Kitchen

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Pool

Free parking on premises

Air conditioning

Stay near Madison's top sights

Hammonasset Beach State Park83 locals recommend

Chamard Vineyards Bistro28 locals recommend

Chatfield Hollow State Park15 locals recommend

Other great holiday rentals in Madison

4.96 out of 5 average rating, 28 reviews

Apartment in Westbrook

Meadowview & Pondside Retreat

LaurenRating, 5 stars1 week ago

We had a lovely stay at this beautiful home! We actually ended up having pictures taken in the backyard because of how gorgeous the scenery is. Becky was super responsive and friendly. Definitely would love to come back! :)

4.96 out of 5 average rating, 26 reviews

Home in Westbrook

Barnacle Bay Beach House

AshlynRating, 5 stars6 days ago

My husband, dog, and I LOVED our stay here- so much that Danielle accommodated for us to stay an additional day! It was the perfect location. Private enough where we felt secluded, but yet right off of a main road with so many great restaurants to walk to! The beach was about a 5 minute walk, and left us with the perfect spot and feeling like we had the beach completely to ourselves the days we were there. We are already talking about going back, and can’t wait to plan our next trip. Thanks so much!

Superhost

Cottage in Clinton

4.83 out of 5 average rating, 40 reviews

The Beach Nest-Lux Cottage Steps to the Beach

ChrisRating, 5 stars1 month ago

Great, beachy location within easy driving distance of a bunch of great waterfront restaurants. Easy, clean, and very comfortable.

4.93 out of 5 average rating, 15 reviews

Home in Madison

Fabulous pool in beach town!

DovidRating, 5 stars9 months ago

We took the house for a family getaway, and it far beyond surpassed our expectations. From the cleanliness of the home, to the beauty and utility of the pool. There was an abundance of all things you can expect to find in a home, e.g. the bathrooms were stocked with an abundance of name brand shampoos and soaps. We enjoyed the beautiful coastline that was in close proximity to house. And we spent hours at the pool on a daily basis, it was very private. Cindy was responsive to our every need and query. She even came by a couple of times to help us out with some issues, she went beyond her call of duty. All this she did graciously, as if it’s not even a bother. She is a true super host.

5 out of 5 average rating, 6 reviews

Guest suite in Clinton

Private 2-room suite + bath in beach town

TraciRating, 5 stars2 weeks ago

Loved it! What stood out for me was peepers at night and the birds in the morning! The bed is so comfortable, and what a bonus.... snacks! Loved the little touches! Looking forward to staying again!

Guest suite in Madison

4.88 out of 5 average rating, 8 reviews

Vintage Cabin Suite with full kitchen (No.2)

JerryRating, 5 stars6 months ago

There was a problem caused by skunk spray, hardly anything controllable by the innkeeper. Amanda handled our need to leave promptly, politely, and professionally.

5 out of 5 average rating, 24 reviews

Home in Guilford

Marina Chic: Bright Seaside Gem

QionglinRating, 5 stars2 weeks ago

The house is very spacious and clean, and best of all it’s filled with sunshine! Lauren always responds quickly and she is super helpful! Would like to come back in the future!