Holiday rentals with outdoor seating 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.

Cozy & peaceful A-Frame, Maine woods, “Birch”

Come relax in our newly constructed, 4 season modern A frame on the Blue Hill Peninsula. Located in the beautiful town of Brooksville, only 10 mins from Holbrook Island Sanctuary, 15 minute scenic drive to Blue Hill and Deer Isle/Stonington or 1 hour to Bar Harbor/Acadia National Park. Stocked with everything needed to enjoy a relaxing getaway- EV Charger too! Is the property not available when you need it? “Maple” A Frame is just next door. See separate listing for availability OR to book both.

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 800 Mbs fiber internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. We’re very pet friendly!

Poet's Cabin - Year-round Acadia A-Frame Getaway

If you're looking for a beautiful cabin in the woods on the Quietside of Mount Desert Island, you've found it! A perfect spot for couple's getaways, solo travelers, families of 3 & friends. Cute, cozy & charming, Poet's Cabin is newly renovated w/ Brentwood queen bed, sleep sofa, stainless oven, dishwasher & microwave. Serene porch to relax on. Private yet convenient setting - close to ocean, hikes, downtown Southwest Harbor, 5min from Acadia's Seawall, Bass Harbor Light, Echo Lake Beach & more.

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Flower Farm Loft

When you arrive at the Flower Farm Loft you're greeted by our dogs, who will likely jump on you with muddy paws and request fetch and pets. You're immediately surrounded by flowers in our gardens and flower studio. The loft has big east facing windows that look over our farm and surrounding fields. You'll open the curtains in the morning to incredible sunrises over Kilkenny Cove, and end your nights at your private fire pit with immaculate star filled skies that will make it hard to go inside.

Whitetail by the River, Acadia National Park 10m

Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Exquisitely Modern Stargazing Cottage @Diagonair

Romantic and secluded, this 2,000 sf modern luxury cottage nestled on 12 private acres is a favorite of honeymooners and lovers of modern design * 1 hour to Acadia National Park & Bar Harbor; 15 min to shopping, hiking, swimming * Stargazing deck * 2 full baths, one with steam shower * Fully equipped kitchen with under-counter fridge/freezer * Two gas fireplaces, one indoors, one on a covered deck * Queen bed with luxurious linens and pillows * WIFI, streaming TV, grill, bar * EV charger

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.

Stonington Harbor Cottage - Vacation / Remote Work

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.

Tiny house with AC!!

A tiny guest house (450 sq ft) overlooking the Benjamin River. AC!!. Enjoy a cup of coffee on your private porch. Living area has a smart tv (no cable, but internet available to access your streaming account). DVD's also available. Kitchenette comes with Keurig with k-cups included, mini fridge, coffee maker/filters, toaster oven, microwave, 2 burner hot plate (no oven), dishes/pots and pans. There is a loft with an army cot. Not suitable for children under age 5.

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).