Holiday houses in Stonington

Modern Coastal Tiny House Retreat + Private Sauna

Welcome to your modern coastal escape in the heart of Stonington — one of Maine’s most charming, artistic, and unspoiled working waterfront towns. This beautifully crafted tiny home blends luxury materials with timeless cabin warmth, offering a unique stay just a short walk from downtown shops, galleries, and restaurants. Relax in your private wood-fired sauna, unwind by the firepit, or watch the harbor glow at sunrise through the loft skylights. Perfect for couples, small families, or friends.

Value · Family · Long stay

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

Value · Family · Indoor spaces

Homestead Cabin

New rustic cabin in the woods near the water. Quiet and peaceful. Family friendly. Great reviews. Walk in the woods, sit on the deck, follow the winding path down to our private rocky beach and if you are brave, swim in Maine's chilly waters! It is a great spot for children to live with nature. The cabin has beds for four, and a futon in the living room for afternoon naps. The fishing village of Stonington is about 3 miles away where you can enjoy lobster just fresh from the sea. Peaceful.

Location · Value · Getting around

Puppa’s View

The perfect vacation property. Private and comfortable 2 bedroom ocean front home with sweeping views of Allen Cove and Penobscot Bay. Just 1 mile from the bustling Stonington Village and a quick drive to anywhere on Deer Isle. The home has dedicated workspaces in each bedroom, a gigantic, fully-equipped kitchen and is spacious and peaceful. Wake to breathtaking sunrise views and find yourself stopping to appreciate the sunset over this quiet cove. I will happily help customize your itineary.

Location · Value · Check-in

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.

Location · Family · Bathroom

Spacious Apt with View of the Harbor

Watch the lobsterman haul in their catch from your scenic bay windows overlooking the charming Stonington Harbor and surrounding islands. Pop downstairs for breakfast at the Harbor Cafe, then stroll to all that Stonington has to offer - Opera House, Isle Au Haut Ferry, 44 North Coffee, art galleries and vintage shops all within walking distance. Stonington Farmers Market and Island Community Center playground. Explore numerous beaches and trails on island. Short drive to off island eateries.

Value · Location · Kitchen

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!

Location · Family · Hospitality

Just Within Reach!

Welcome to the perfect spot to get away from everything. Nestled at the edge of the forest, you'll forget your worries in this simple, spacious and serene space. Open the French doors and enjoy coffee on the deck while you plan your daily adventure. Located about a mile from Main Street, lobsters, restaurants, shops, entertainment and the beach, everything is truly, Just Within Reach. Come and go as you please, then wind for the night listening to the faint horn from Mark Island Light.

Location · Cleanliness · Getting around

Bayview House 1br 2ba Stunning Harbor Views

Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpler time? Or long for days spent on the water or experiencing village life with friendly locals in charming pubs tasting local eats? Experience the simple joys of life with rustic yet modern amenities offered at this coastal 2-story home. Whether daily strolls by the water or taking in the sunset on your deck, you'll fall in love with this lovely New England destination.

Family · Value · Comfort

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.

Location · Value · Beach

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 small propane grill. Two-night minimum with parking for one car only (no trucks/trailers). Ask about extra parking. One well-behaved dog is allowed, note $35 pet fee. No other pets or children. No TV, good wifi. 10pm quiet zone.

Location · Value · Long stay

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

The Ferrykeeper’s Cottage is a light filled oasis, surrounded by water, meadows & views of the famous Eggemoggin Reach. Our cottage offers handcrafted counters, stone sinks, & oceanic tile to create a unique setting. 3 houses to the beach. Borrow a kayak & explore our shore. Property borders Scott’s Landing - a treasure trove of birds, sand dollars, porpoises, seals & a family of foxes. *Queen bed + flip down sofa (latter suitable for 1 adult OR 2 small kids)

Value · Location · Accuracy