Family-friendly vacation rentals in Stonington

4.98 out of 5 average rating, 88 reviews

The exterior of the two-story cottage is shown, featuring gray shingle siding and teal accents. A small porch is visible with a few steps leading up, surrounded by a landscaped area with rocks and shrubs. Warm light glows from the windows, hinting at a cozy interior.

Cottage in Stonington

Raven's Cottage-A two story Gem for Two!

Raven’s Cottage is a two story dwelling nestled in the quiet Greenhead neighborhood overlooking a working harbor & downtown Stonington. You are afforded magnificent views of a working harbor and are located a few minutes walk from the post office, restaurants, art galleries, a museum, coffee shop, Opera House and the Isle au Haut ferry. Architect & Artist owners Restored and designed a compact, contemporary living space from a lobster mans workshop. 7 day minimum stay from Saturday to Saturday

A calm cove surrounded by dense green trees reflects serene water. A sailboat gently floats on the bay, complemented by soft rock formations emerging from the water's surface. Sunlight brightens the landscape, casting a tranquil atmosphere over the scene.

4.95 out of 5 average rating, 175 reviews

Blue Arches: waterfront vacation home on 18+ acres

A lovely custom-designed home nestled in a pristine oceanfront cove, Blue Arches offers 18 acres of privacy and relaxation on beautiful Deer Isle, Maine. Charming Stonington Village is just five minutes away & features harbor-front restaurants, shops, kayaking adventures, galleries and the acclaimed Opera House Arts center. Day trips to nearby Bar Harbor, Mt. Desert Island and Acadia National Park expand your possibilities and let you create a truly memorable vacation for your friends & family.

4.98 out of 5 average rating, 57 reviews

A view of Stonington Harbor showcases a charming waterfront scene. Several boats are anchored in the water, with the shoreline lined by lush greenery and a variety of houses. A blue sky and bright sunlight enhance the tranquil maritime atmosphere.

Cottage in Stonington

Short walking distance to the Town of Stonington

Are you looking for the complete Maine experience? If so, this is the place for you. Walk within minutes to downtown Stonington where all the restaurants and shops are located, or just across the road to the Stonington Lobster Co-Op where you can buy your lobsters straight off the lobster boat. Also within short walking distance is famous “Ames Lily Pond”, the Isle Au Haut boat company, Island approach’s where you can rent kayaks, book boat tours and so much more. While enjoying the best views!

4.88 out of 5 average rating, 214 reviews

A wooden pathway leads towards a serene water view, bordered by lush greenery. A picnic table and several chairs are positioned on a gravel area adjacent to the water, offering a perfect spot for relaxation and enjoying the scenery under a clear blue sky.

Cottage in Deer Isle

Private Waterfront Home with Kayaks and Firepit

Retreat to your own coastal oceanfront paradise, where each day begins with breathtaking views. A private boardwalk leads to your secluded beach — perfect for morning strolls, exploring tidal pools, or launching kayaks into sparkling waters. Evenings bring fireside marshmallows under the stars with waves as your soundtrack. Whether you seek adventure with scenic drives to Acadia National Park or quiet mornings with coffee, sea breezes, and seabirds, this is where comfort meets Maine’s coast.

Superhost

A spacious house is nestled among lush greenery, featuring multiple balconies and large windows. The structure is painted in light hues, blending harmoniously with the surrounding trees. A natural ground cover of ferns provides a serene atmosphere, inviting guests to explore the outdoor space.

Home in Deer Isle

Private Oceanfront Maine Living!

Relax with the whole family at this peaceful house on a private cove! Located on stunning Deer Isle, just minutes from both Deer Isle Village and Stonington Harbor, yet set down a wooded road with direct ocean access. This home has everything you need for a family vacation - stocked kitchen, cribs, pull out couch, grill, toys, books & board games, smart tvs, beach towels, and plenty of outdoor space. This was previously our family home and we’d love to share the best of the island with you!

4.72 out of 5 average rating, 32 reviews

Four wooden Adirondack chairs are arranged in a semi-circle around a fire pit, positioned in front of a gray two-story house nestled among trees. The house features multiple windows and a deck overlooking the serene natural surroundings.

4.95 out of 5 average rating, 40 reviews

Cute cottage on a tidal cove

Enjoy the best Deer Isle has to offer in this clean and compact four season house in Oceanville. Only 2.7 miles from Stonington, the house is secluded yet convenient. Cool in the summer and warm in winter with central heating and a wood stove when it's chilly. Built in 2015, it has everything you need for a wonderful island vacation. A recent basement renovation created a third bedroom/recreation room. Elevated bog walk for tidal kayak put-in and NEW level 2 electric car charger for guests.

4.95 out of 5 average rating, 123 reviews

Apartment in Stonington

The American Eagle - Inn on the Harbor

The American Eagle is a gorgeous unit with 2 bedrooms: one with twin beds and a master bedroom room furnished with one queen, full bath, hairdryer, tv with cable, and free wifi. The fully furnished kitchen is equipped with pots and pans along with plates and cutlery. Enjoy the dining room set for four or relax in the cozy sitting area with a large window facing the harbor and an electric fireplace. Access to a private deck and stunning harbor water views of Stonington's historic waterfront.

5.0 out of 5 average rating, 116 reviews

The cabin is nestled among lush greenery, featuring a modern wooden exterior with multiple windows. Elevated on stilts, it harmonizes with the natural surroundings of ferns and trees, allowing for a serene atmosphere in a tranquil forest setting.

Cabin in Sedgwick

The Cabins at Currier Landing Cabin 2: Meadow

Tranquil cabin; open plan. Bedroom w/queen bed & privacy doors. Alcove w/bunkbeds. The Cabins at Currier Landing, featured in Dwell as “Three Magical Tiny Cabins Take Root in a Maine Forest,” are located on the Thos. Currier Saltwater Farm. Glimpses of water & access to 300’ of the Benjamin River Harbor shore. 2 seasonal cabins; 1 studio cabin. Centrally located on the Blue Hill Peninsula near Deer Isle, the cabins offer access to outdoor activities, cultural events, restaurants & shops.

A charming light-colored condo is displayed, featuring a mix of shingle and clapboard siding. Vibrant flowers and greenery surround the entrance, which is framed by a white picket fence. A bright blue door stands out, and an American flag gently flutters in the breeze.

4.95 out of 5 average rating, 65 reviews

Stonington Dream House

Welcome to Schooner! Schooner is a light filled, first floor condo that lives like a single family home. LOCATION * LOCATION * LOCATION the home overlooks Main Street, Stonington Harbor and the gorgeous archipelago beyond. Enjoy all of this charming coastal town. Walk everywhere! Coffee house, library, restaurants, museum, opera house, charming shops, plein air painters, photographers, cool art around town and more. This is what coastal Maine dreams are made of. We love to share this town!

4.94 out of 5 average rating, 101 reviews

Blue Heron

Blue Heron, recently renovated with modern amenities, is conveniently located near local art, culture, restaurants, and fine dining. Its beautiful Burnt Cove sunsets, peaceful private settings, and natural ambiance make it a favorite among couples, solo adventurers, and families. The spacious front lawn offers ample space for relaxation. Just a short walk away, you can enjoy a lobster bake on the shore, launch your kayak in the backyard, or explore the local shops within a mile’s reach.

4.99 out of 5 average rating, 133 reviews

The exterior of a charming tiny house showcases a light gray wooden façade and a green roof. The building features several large windows, allowing natural light to enter. Surrounding trees and rocky terrain add to the serene landscape.

Cottage in Stonington

Stonington Harbor Cottage

SPECIAL: 10% discount for a 28+ day stay. This bright and cozy two-room TINY HOUSE was built in 2018 as a honeymoon suite. A full kitchen with cookware, dinnerware, coffee pot, microwave. A heat pump provides heating and cooling. Shaded picnic table and propane grill. Parking for one car only (no trucks/trailers). Ask about extra parking. One well-behaved dog is allowed only, with a 45 lb weight limit, $40 pet fee. No other pets or children. No TV, good wifi. 10pm quiet zone.