Holiday rentals with outdoor seating in Westbrook

The Millhouse Downtown Chester

An upscale destination with accommodations for foodies & friends in the heart of historic Chester CT. Stay at this beautifully renovated historic Millhouse in charming downtown Chester. Enjoy strolling the streets loaded with shops, award winning restaurants, a microbrewery, art galleries, and more. All within a 1 minute walk. Our prime location is just 20 minutes to the CT shoreline and located in the heart of the CT River Valley. The Millhouse is next door to the Chester Historical Museum.

Charming Chester Retreat - Cottage

Come soak up the last of summer! This 2 bed, 1 bath unit has been redesigned to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Beach Access 10 min away at Cedar Lake. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! New England getaway / Hidden Gem / Retreat/ Beach Access

Amazing 2BR Riverfront Gem

Unwind at this happy getaway on the river. Comfy cozy with amazing views of River. Convenient to beaches, and includes free pass to the Clinton Town Beach! The well-equipped, intimate kitchen overlooking the river is a pleasure for any cook. You will love our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to groceries, coffee shops and amazing CT scenery! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants with music, and lots more.

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.

Beautiful View Cottage

Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.

“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.

Guest House at the Marina

Traveling nurses, academic rentals happily considered! A beautiful, modern one bedroom apartment on the second floor with a gorgeous view of the Indian River and tidal marsh. It is 600 sq feet, completely renovated, with a queen size bed, a well-appointed kitchen & bathroom. Walking distance to the Clinton train station. Stays in-season include use of 2 kayaks or SUPs per day (2 hours) provided by Indian River Kayak from Memorial Day to Labor Day.

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.