Holiday rentals with outdoor seating in Madison

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Spacious Oceanfront Getaway with Spectacular Views

Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

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.

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”.

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.

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.

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

HGTV reno! Fall Foliage, near New Haven, Firepit!

*Inquire now monthly discount Jan* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speeds

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! ☀️

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!