Family-friendly holiday rentals in Stonington

Mystic Bungalow - 6min Walk Downtown!

Thoughtfully designed with coastal living in mind! Located in the heart of Mystic, 5 min walk to historical Mystic Bridge, 10 min walk to Mystic Seaport, 10 min walk to train station and short drive to Olde Mistick Village, prime location makes it easy to explore! Free parking and beautiful back deck. Located in a duplex, you will have the top unit, my family friend lives on the bottom. I live a few streets over and am happy to give local recommendations! Will be decorated for Valentines Day!

"Mystic Country" Farm Stay at 100 Acre Wood

Let us welcome you to 100 Acre Wood, a historic farm and working cattle ranch. Owl's House is a private and stylish guest house nestled within the trees and garden and offers 180° views. Our farm store is stocked with our own TX Longhorn beef and pasture-raised chicken and eggs, plus curated with local products. Enjoy pastoral farm life and our private forest trails, or get out and play in the area's abundance of fine dining, wineries, seasonal attractions, outdoor activities, and entertainment.

Scenic Island Summer Home

A beautiful home on scenic Mason's Island. The house is located a few minutes drive to historic downtown Mystic. Spend your days exploring town, before coming home to your oasis at the end of a quiet cul de sac. The 3 bedroom 3 bath home has plenty of space for you, your family and friends, and has a great backyard with patio, grill, outdoor sectional and dining table, perfect for summer days and nights. Our home is the ideal home base after days at the beach, on the water, or exploring Mystic.

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!

Mystical Ocean View in Historic Stonington Borough

Enjoy stunning ocean views of Stonington Harbor and Fishers Island Sound from multiple floors of this spacious, comfortable apartment for 6. Located in historic Stonington Borough, Connecticut's oldest village, you can relax in the private library, then explore this picturesque area with acclaimed restaurants, shops, and museums all within walking distance. And with Downtown Mystic, I-95, and RI's beaches just a short drive away, you can have it all, located half way between Boston and NYC!

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

Harper House Heart of DT Mystic Luxury Getaway

Historic Downtown Mystic. This immaculate designed retreat is professionally managed and offers an enjoyable winter stay. Just steps to Deep Water Marinas, Fine Restaurants including Captain Daniel Packer Inn, SIFT Bakery, Train Station, and Unique Shops. This modern apartment features a fully equipped high-end kitchen with a microwave, blender, toaster, cooking essentials, and a Keurig machine. 1 on-site parking space and a shared common backyard space if available for your enjoyment.

Morgan Suite - spacious | hot tub | water views!

The Morgan Suite is a private Airbnb located in a quiet neighborhood along the Pawcatuck River. Just minutes to downtown Westerly, downtown Mystic, beaches, breweries, wineries, shops, restaurants and much more. This Airbnb a perfect for a romantic getaway or a relaxing memorable vacation with a friend. If you are looking to explore a new area and relax, the Morgan Suite is for you! The home is spacious, newly renovated with excellent amenities. Newly added - hot tub and massage chair!

Eco Friendly 1700s home! 0.3 miles to Westerly RI!

Welcome to Farley Ave! Our 1700’s home was originally a barn to the farm house next door, hence the close proximity and lower original ceilings/beams. Both were converted to a homes in 1905 and then we restored this house in 2021 to give it the character it once had, and bring it back to life. Our home is walking distance to bars and restaurants in downtown Westerly, as well as 10 minutes from Westerly beaches and 10 minutes to Mystic CT! Equipped with bikes, beach essentials and more!

Waterfront Retreat on the Mystic River

This kayakers paradise is a waterfront home secluded on 2.5 wooded acres along the Mystic River. Views of the water, tidal marsh, woods, and wildlife are constantly changing. Owned by two designers, this home’s modern aesthetic has interesting art, objects, furniture, lighting & textiles. Dine & relax on the porch, paddle kayaks on the river, walk on the scenic road into downtown Mystic, or visit nearby beaches and family destinations.

Home Away From Home - 3bdr 1 ba

Welcome to our Home Away From Home, where you will be closely located to Westerly downtown, the beach, shopping, dining, Mystic, the Casinos, and Watch Hill (which is where the beautiful Ocean House and Taylor Swifts home is located). Our home is family friendly and offers all must-have items for your littles. But even without littles, our home offers a spacious and comfortable atmosphere for all guests.

Heart of Stonington Borough! Ocean View Loft

Beautifully renovated 3rd floor loft with ocean views in the center of town. Our home is walking distance to restaurants, shops, and water access (town beach DuBois Beach). Centrally located between charming CT shoreline towns - Mystic & Westerly. Get the full bed and breakfast experience and order from our neighbors, the famous Noah's Restaurant!