Holiday houses in Madison

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Top-rated holiday rentals in Madison

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Top Guest favourite

Guesthouse in Guilford

4.99 out of 5 average rating, 501 reviews

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.

Top Guest favourite

Guest suite in Clinton

5 out of 5 average rating, 15 reviews

Private 2-room suite + bath in beach town

Enjoy 2 rooms + bath. The second floor of my home will be your own private oasis. Large dog (+ cat) on premises (no access to suite). Please be dog-friendly! Spacious bedroom, cozy sitting area, queen bed, TV w/ premium channels. Separate dining/kitchenette with Keurig, microwave & fridge. Brand new private bath with tub/shower. 3 wooded acres by Menunketesuck River. 2-level deck with fire table, patio, propane grill and hot tub. Near premium outlets, beaches, state park, Chamard Vineyard.

Top Guest favourite

Apartment in Guilford

4.99 out of 5 average rating, 280 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Superhost

Home in Madison

5 out of 5 average rating, 4 reviews

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.

Top Guest favourite

Guesthouse in Madison

5 out of 5 average rating, 56 reviews

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.

Top Guest favourite

Guesthouse in Guilford

4.95 out of 5 average rating, 105 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

Kick back and relax in this calm, stylish home, yards from private lakes for kayaking, swimming, fishing or skating in season. For the adventurer, enjoy year round access to extensive forest trail systems for hiking, mountain biking, cross country skiing, and snowshoeing, only a 2 minute walk from our door. Nicknamed " Guilford's Little Augusta," the 9 hole, par 27 executive Guilford Lakes Golf Course is only 1/4 mile away. Five miles south lies one of the 5 most beautiful town greens.

Superhost

Guest suite in Madison

4.72 out of 5 average rating, 18 reviews

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.

Top Guest favourite

Home in Madison

5 out of 5 average rating, 32 reviews

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

Guest favourite

Apartment in Clinton

4.87 out of 5 average rating, 38 reviews

Bright & Cozy Loft Near Beach

Enjoy a peaceful and bright retreat in Clinton! This spacious studio offers plenty of natural light from skylights, creating a cozy atmosphere. Located 10 minutes from Clinton Beach, Hammonasset State Park, and Clinton Premium Outlets. The entrance is up 15 steps to your private, separate space on a shared property. With a private bathroom and all the essentials for a comfortable stay, you’ll enjoy a relaxing experience in a quiet neighborhood, near dining and shops.

Top Guest favourite

Guesthouse in Madison

4.97 out of 5 average rating, 78 reviews

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.

Top Guest favourite

Guesthouse in Madison

5 out of 5 average rating, 12 reviews

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.

Guest favourite

Guesthouse in Madison

4.97 out of 5 average rating, 116 reviews

Beachy & Bright Coastal Escape - 5 Mins to Beach

Charming coastal guesthouse in Madison’s historic district—just a 5-min walk to a private beach, 5-min drive to town, and 20 mins to New Haven. Bright, beachy, and newly renovated with a king bedroom, full kitchen, private deck, and huge backyard. Set on nearly an acre in the heart of New England, it’s perfect for couples, families, and girls’ getaways. Walk to cafes, shops, and the iconic RJ Julia bookstore.