Holiday houses in Southwest Harbor

Harborside~Seaglass Beach~Dock~5 min to Acadia

Harborside on Main is a lovingly restored, traditional coastal New Englander cottage located on the hillside above beautiful Southwest Harbor, just 1 mile from Quietside Acadia’s best oceanfront hiking trails. Steps outside the maritime village of SW Harbor with semi-private ocean access, seaglass beach, dock, firepit, and a short walk to all village amenities: the town pier, local bars, restaurants with live outdoor music overlooking the marina, & a private charter on a wooden Friendship sloop.

New! Centrally located on MDI, near Lakes/Acadia

This beautiful newly built loft has three bedrooms and two full bathrooms. Inside, you’ll find a clean and cozy retreat that sleeps up to six. Step outside to the patio and unwind by the fire pit, or relax on the inviting front porch—perfect for morning coffee and birdwatching. We are centrally located on MDI - close to ponds, lakes and the Atlantic, hiking in Acadia as well as near coffee shops, restaurants and shopping. This home is the perfect spot for soaking up all our island has to offer.

Pilot House

Named for a boat shipwrecked on its shore nearly a century ago, Pilot House boasts gorgeous views of the working harbor and outlying islands. The oceanfront house on spacious grounds is comfortable and up-to-date, with water views from the large high-end kitchen, open-plan living and dining areas, master bedroom, lower-level guest room, and upper deck. Outside spaces include front and back gardens and a small waterside platform for watching the boat traffic. Town center is a short walk away.

Captain Whitmore Cottage

Located on a dead-end street within walking distance of village restaurants & small shops, the Captain Whitmore Cottage is just 20 yards from the shoreline, accessible via a right-of-way path. Enjoy breakfast or evening cocktails on the deck to the cacophony of calling gulls and chugging lobster boats. Only 10 minutes from Acadia National Park, this spacious 5 bedroom/2 bath cottage is the perfect summer escape featuring 2 living & 2 dining areas, a well-equipped kitchen and a cheery sunporch.

Tilia Retreat-Relax & Explore @ Acadia

We are excited to share our 3 bedroom, two story residential home on the “Quietside” of Mount Desert Island. A 15 minute walk to the nearby shore and town pier. You will be 5-10 minute drive from some of Acadia National Park attractions and hiking trails; i.e. Bass Harbor Headlight, Ship Harbor, Wonderland, Flying Mountain and Seawall Picnic Area. (a great spot to see the Sunrise). Long Pond and Echo Lake are close by locations for kayaking and swimming. Bar Harbor is a 20 minute drive.

Evergreen Hill in Acadia National Park

Evergreen Hill is a cheery cedar cape set up on a private half acre of fir and native blueberry. Just a mile from Acadia trails and beaches, this humble cottage has a peaceful island vibe, relaxing family spaces, a fenced yard, and great front porch, with no dog or cleaning fee. Eat lobster year round, visit Bar Harbor, take the family on a boat ride to see Mount Desert Island's 26 peaks from the water. Come in winter to work and play, hike the snow covered mountains, ice skate and XC ski.

Spoonhandle Cottage

Newly renovated oceanfront cottage on Southwest Harbors working waterfront with a minutes walk to downtowns many restaurants and shops. The first floor offers a modern kitchen with all amenities, double sofa bed, full bath and laundry. From the wrap around deck watch the sunrise overlooking the Marina and beach. A full bath, two bedrooms with balcony access on the second floor will complete your vacation retreat. Free parking off Main Street with a landscaped path down to the cottage.

"Yellow Door”

The Yellow Door | A Quietside Retreat Skip the Bar Harbor traffic and settle into the "Quietside" of the island. Yellow Door is a high-end, 2-bedroom apartment in Southwest Harbor, designed and built by one of the area's most respected local builders. It’s got that clean, custom craftsmanship that feels less like a rental and more like a home. The Layout: Bedroom 1: 1 King Bed Bedroom 2: 1 Queen Bed Bath: 1 Full Bath The Vibe: Exquisitely decorated with a focus on local design.

On the water. Walk to Southwest Harbor

If you want to be near the action of an active and interesting harbor, this is the place for you. You will have a front row seat to spectacular morning sunrises over the harbor, the comings and goings of the fishermen and the many boats docked at the marina and anchored in the harbor. This spacious four bedroom, two and a half bath home is located at the Great Harbor Marina just half a mile from downtown Southwest Harbor. Walk to restaurants, art galleries, specialty shops and more.

Seaside Cottage, Southwest Harbor & Acadia

Our cozy family cottage on the "Quiet Side" of Mount Desert Island has panoramic views of Southwest Harbor and the Cranberry Islands. Watch the tide and boats come and go from your bed! High tide splashes below the cantilevered deck. Quaint downtown shopping & dining is just 3/10 mile along a sidewalk. Several access points to Acadia National Park less than 5 miles away; downtown Bar Harbor is a 25 minute drive. The cottage is ideal for couples or families with supervised children.

Sea Breeze

This is a two bedroom and one and a half bath upstairs apartment. It is located in the center of downtown Southwest Harbor. Surrounded by restaurants, boutiques and art galleries. Walk downstairs to enjoy all Southwest Harbor has to offer. The apartment is walking distance to a working waterfront harbor where you can watch the fishing boats come and go. Mount Desert Island is surrounded by Acadia National Park all within a short drive from the apartment. No Cleaning Fee!!!

Oceanview in Southwest Harbor

Enjoy a harbor ocean view right from the comfort of home. Admire the ships as they come and go and take in the beautiful sunsets right from your patio. An oceanfront property located in a peaceful neighborhood. Has beach access right from your front door. Within walking distance to downtown Southwest Harbor shops and restaurant's. Less than a 5 minute drive to Acadia National Park walking/hiking trails and beaches. A great place to relax after a day in the park.