Holiday rentals in Southwest Harbor

Garage, a Modern Oasis

An architectural gem in Acadia, designed with soaring ceilings, walls of glass, and effortless indoor-outdoor flow. From elaborate landscaping to finest interior finishes, every element was chosen with intention. Interiors are appointed like a boutique hotel: premium furnishings, curated local art, and the finest bedding. Multiple living areas and a shaded deck, an enclosed carport alongside ping-pong, and a basketball half-court. EV charging on-site. As featured in Fine Homebuilding, June 2023.

7 Minutes to Acadia, Steps from Town, Harbor Views

Come discover why the "quiet side" of Mount Desert Island is really where the action is! Located within walking distance of everything downtown has to offer, this cute New Englander style home with harbor views is the perfect base to explore all the treasures of MDI. Just a short drive to some of the best attractions Acadia has to offer and located on the Island Explorer route so you can travel around hassle free. Be among the first to enjoy this all new renovation! This home is a renovated 180

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.

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.

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!!!

Cheerful 3-Bedroom Cottage moments from ocean

Mimi's Cottage is your getaway home located in the heart of Mount Desert Island. Acadia National Park is next door, as well as lighthouses, the ocean, and many outdoor activities for the whole family. We offer a welcoming rental experience for large and small groups. We are within moments of the ocean and our quaint little village of Southwest Harbor. Mimi's Cottage is thoughtfully furnished for young and old, and offers the perfect space for your Downeast Maine adventures.

Harborside Comfortable Cottage! [Mermaid Cottage]

The PERFECT location in Bass Harbor to enjoy all the sights and smells of a real Harbor in Maine! Located right on the edge of the water in downtown Bass Harbor, this unit is a perfect place to relax as you explore Acadia! The windows in the living room open to the water for amazing views! Location Highlights: -6 min Drive to Downtown Southwest Harbor -25 min Drive to Acadia National Park [Cadillac Mountain Entrance] -30 min Drive to Downtown Bar Harbor

Manset Rock Cottage:A Coastal Retreat on Mt Desert

Nestled on Mount Desert Island’s Quietside, Manset Rock Cottage offers breathtaking views of Acadia National Park, Southwest Harbor, and the Western Way. This charming 4 bedroom home features a spacious great room with a fireplace, a full kitchen, and a large deck with woodland and ocean views. Stroll the private nature trail to the pebble beach and relax as sailboats drift by. Perfect on its own or rented with the Main House—your coastal escape awaits!

Sweetwater - Bright, Airy, Modern

Named for its sweet views of the ocean inlet just beyond the front patio, Sweetwater is a serene Scandinavian-modern retreat nestled on the "quiet side" of Mount Desert Island — home to the beloved Acadia National Park. Whether you're gathering family or escaping with friends, this thoughtfully designed cottage offers everything you need for a restorative Maine getaway, just minutes from the Park's most cherished trails, swimming holes, and hidden gems