Guesthouse holiday rentals in Stonington

Cliffside Guesthouse in Mystic Historic District

Let the Cliffside Guesthouse become your gateway to the fun, excitement and relaxed New England charm of historic southeastern Connecticut. Cast off the burdens of daily life and journey to Mystic, a historically avant-garde seaport community that combines the best of both yesterday and today. Located just steps from the Mystic River, and situated only blocks from the center of our historic hamlet, and close to award-winning restaurants, the Seaport, the Aquarium and Mohegan & Foxwood Casinos.

Super Adorable Cottage + Fire pit + King Bed!

Transport yourself to Mystic's shipbuilding heyday at Smith Cottage. This adorable, open-concept, pet-friendly, two-bedroom retreat in historic Old Mystic captures the essence of a bygone era. Nestled at the head of the Mystic River, it offers a perfect base for exploring the coastline and Mystic Seaport. With Colonial nautical charm and 21st-century comfort, the Smith Cottage invites you to experience genuine New England hospitality. Your journey into Mystic's maritime history begins here!

Ocean Shire Coastal Retreat + Beach Pass

Ocean Shire: Warm modern updated private coastal cottage located 3 miles of stunning beaches (Misquamicut and Watch Hill). Season beach pass included. Kids welcome. 1100 sq. ft, two bedroom, 1.5 bath attached cottage on 1.4 acres. Watch Hill/Ocean House: 5 min. drive Mystic, CT: 10 miles Stonington, CT: 8 miles Newport, RI: 38 miles Wooded yard is a beautiful tranquil outdoor space. Easy access to shops, restaurants, bars, sailing, water sports and beach are all available at your door.

Charming Post and Beam cottage (near Foxwoods)

Our Post and Beam Cottage offer a rustic feel and is tucked away on a country road. The Area offers a lot of sites to visit: Mystic Seaport and Aquarium, Foxwoods & Mohegan Sun Casino, Mashantucket Pequot Indian Museum, Wineries, Submarine Museum, Westerly RI Restaurants, Beautiful Beaches of Rhode Island (Watch Hill & Misquamicut State Beach), the quaint & charming village of Stonington and the beautiful & scenic Billings Lake of North Stonington. Hiking and a lot of Trails close by.

The Offshore - A Walkable Wakefield Carriage House

The Offshore is a newly built, airy and clean one bedroom apartment above a modern carriage house fully stocked with all of the comforts of home. The apartment is centrally located and serves as an ideal landing spot for a southern Rhode Island getaway. You have the option to take the bike path to many beaches and Narragansett Pier or walk two blocks to Main Street Wakefield for a morning coffee at Caf Bar, Phils or South Country Bread Company and post beach ice cream at Brickley's.

House on Little River / Writer Retreat

Rustic cottage on on Little River, a lovely trout stream that swishes around rocks. Great place for kids to play! Lake across the street. Canoe. Woods all around. Very quiet except for hush of river. Nice deck extends almost to the river. Charcoal grill. In all ways cozy and pleasant. Nice for couples, writers, artists, travelers, families, and pets—a place for quiet, peaceful people. About the lake: There's no beach. Access is just a narrow path down to the water.

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Cute Little House in Town

Cute little guesthouse perfect for two people, but could also work for three with advance notice. There is a queen bed upstairs, and a couch downstairs, there are two fold out cots available upon request. The deck overlooks the huge backyard. The television has a Roku boxes so you can watch Netflix, Amazon Videos, etc. I have a friendly dog named Barney who is often outside on the property.

True Artist Loft, 5 minutes to downtown Mystic

A Historic Artist’s Retreat Near Downtown Mystic Lovingly known as The Dacha for nearly 80 years, this one-of-a-kind gem was built in 1945 as a studio for the artist who once called the property home. Fully insulated for cozy winter stays, the unique structure is tucked away on a peaceful piece of land, just five minutes from downtown Mystic.