Pet-friendly holiday rentals in Madison

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

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.

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

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”.

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.

Shabby Chic Retreat

Greenfield Cottage has been described by our guests as a cozy place with all the amenities for a comfortable stay. GC is located just minutes from town beaches, Hammonasset State Park as well as the village center. Madison and nearby towns of Essex and Chester offer a variety of casual and fine dining plus many boutiques. At GC you can enjoy al fresco dining on the back deck where there is a grill and fire pit. GC IS AVAILABLE AS AN ACADEMIC RENTAL FROM OCT 6 2025 - May 31 2026 -- $3200/MO*

Fall Sale! Cozy Bungalow/Pet-friendly/Walk2Beach

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.

Cozy Home In Short Beach Community

A cozy home in a beach community that has a central location with easy access to outdoor activities & local restaurants. The home is also 5 minutes from the Branford Train Station, Stony Creek Brewery, & Branford's town center. We are also a 10 minute drive from New Haven, home to Yale University, Yale Hospital and other colleges/universities. Our guests also gain access to Johnsons' Beach, a private residents only beach, located just around the corner from the home(4min walk/900ft)

Seagrass Bungalow

🌾Seagrass Bungalow is a sun filled, romantic, peaceful, back to nature, mini-home, that is exactly where you are meant to be! Private & surrounded by seagrass blowing in the breeze & cheerful birds waking you with the sunrise. Seagrass Bungalow is the perfect getaway for two & their small pup. Do yoga on the private deck, shower outdoors in the sunlight, grill local corn, have a cocktail by the firepit, or get out & walk to the cutest town green, shops, restaurants, & beach! ☀️

Storybook 2 Bedroom Cottage

Enjoy a relaxing stay at this charming storybook home which has just been refreshed professionally and redesigned with unique and gorgeous antique furnishings and decor. Built in 1895, the home was re-envisioned by designer Charles Spada in the 90’s. A lovely private back yard with beautiful stone work and plantings. The proximity to shopping, galleries, restaurants and Old Saybrook, Town Beach and Katherine Hepburn theater makes this location ideal.

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.