Holiday rentals with outdoor seating in Deer Isle

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.

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.

Cozy Cottage on the Penobscot — Panoramic Luxury!

Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 12 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

Cozy & peaceful AFrame in Maine woods “Maple”

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? “Birch” A Frame is just next door. See separate listing for availability OR to book both

Sunny Waterfront Home Overlooking Blueberry Field

5 acres of lawns, gardens, and meadows and a gentle rocky beach on Blue Hill's Salt Pond, a protected inlet of the Atlantic Ocean. The house faces south towards the water and overlooks a gorgeous blueberry field that turns a majestic shade of deep red in the fall. Please feel free to reach out with us for more information or to inquire about a longer term booking. The house has two bedrooms and baths on the main level and an two additional bedrooms, bathroom, and living space downstairs.

Exquisitely Modern Maine 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 and 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

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.

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.

NEW Whitetail Cottage, Acadia National Park 7m

NEW Whitetail Cottage East only 6.9 mi to Acadia National Park Maine - a hikers paradise! Centrally located for a perfect Acadia Adventure! Book for the convenient location - stay for the style. Tiny home has WIFI & SMART TV. Off the main(e) drag but nestled in a wooded property 1/2 mile from Bar Harbor Rd/Route 3 down the road from Mount Desert Island and a stones throw from multiple authentic Maine lobster pounds. Perfect for 2 . A short drive to MDI, Acadia, Bar Harbor,Southwest Harbor

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 400 Mbs cable 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. Pet friendly!

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.

Artsy Tiny House & Cedar Sauna

Our family is excited to share our tiny house with you! Located on our artist collective farm, this is our favorite place on earth. It’s off grid, cottage core, and has a beautiful & fragrant cedar sauna. We are 27 minutes from Acadia National Park and surrounded by truly gorgeous local beaches. We offer super comfy beds, an outdoor shower, twinkle lights, summer nights filled with fireflies, bright maples in the fall, and cozy winter movie nights in a bed alcove like on a boat.