Vacation rentals in Madison

Rural Homestead Stay in Your a Private Suite

Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard amongst the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

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”.

Fall Sale! Cozy Bungalow/Walk2Beach/Pet-friendly

Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

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.

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

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.

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.

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

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.

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.