Guest house holiday rentals in Stonington

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!

The Hospitable Homestead-Kid Friendly & Pets too!

Our humble Homestead sleeps 7 and is kid & pet friendly! This spacious second floor apartment features an oversized bedroom that can easily fit a pack n play or doggie bed! There is a dedicated work space with a desk & office chair by a window overlooking the backyard. A tucked away twin bed allows for extra sleeping & privacy in a tiny room off the main hallway. With quick access to the highway, just seven minutes to the center of town, numerous shops & dining await. Suitable for Remote work.

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.

Spacious, unique barn with beautiful views.

Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our field and the visiting deer. The eclectic decor is accumulated from years of activism. Our guest room and bathroom are newly renovated. It is a quiet and peaceful area near two state parks. We operate a mail order business in the downstairs area but will not be working while guests are staying with us.

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.

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.