Holiday rentals with outdoor seating in Madison

Modern Carriage House Near Beach - Deck + Fire Pit

Come stay on the closest property to Hammonasset Beach State Park in all of Madison! Just 1 mile and your feet are on 2 miles of white sandy beach to explore and enjoy. This fully renovated carriage house is nestled on a grassy 1.5-acre property near town. Enjoy your own private entrance, full kitchen, sunny deck, fire pit, and outdoor dining space. Located across from the Greenway Trail and close to shops, restaurants. Ideal for couples or small families looking for a relaxing coastal getaway!

Get Back to Nature at a Modern Wood Clad Getaway

SUMMER IS HERE--Glorious birds. Come and enjoy a wonderful time in our guest house. You can Hike on the trails, and swim in 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. 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.

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”.

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, please message us. Our lovely, well designed place is in an ideal location. A sunshine filled living room w/high ceilings, a private bedroom in back, and large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique. We're neighbor to some of the BEST restaurants, art and shopping in CT! We know you'll enjoy your stay!

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.

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.

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

“The Answer” Your Unique, Tidal, Riverfront Escape

“The Answer” is listed in “Only In Your State” 2024 - titled “This Riverfront Retreat Will Be Your New Favorite Destination” and Travellers Worldwide 2022 and 2023 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil tidal water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

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.