Pet-friendly holiday rentals in 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 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!

The Farm-- A Lovely Place and a High-End Space!

TAKE ADVANTAGE OF OUR APRIL2025 DISCOUNT! This upscale and modern home was fully renovated in 2020 with your comfort in mind! Nestled in the woods and just steps from the Seal Cove entrance to the National Park, “The Farm” is also just 1.5 miles to downtown SW Hbr’s bustling village. It features a high-end kitchen, 3 well-appointed bedrooms, 2 full baths, an expansive game room with card and puzzle table, air hockey, and a unique screened-in porch w/cathedral ceiling and wood burning fireplace!

"Schoolhouse," a Boutique Home & Writer's Studio

Formerly a schoolhouse on the "quietside" of MDI, this home was redesigned by a NYC architect (Wake), and sits a block from the harbor in Manset, home of Acadia National Park. An additional exterior dwelling accommodates guests who desire an "away space" for work or solitude between hikes and al fresco dining. Bosch and Cafe appliances, local original art, Ann Sacks tiles, the finest linens & custom woodwork celebrate this home in a Scandinavian modern vibe. Vespa charging. Room for 1-2 cars.

Quiet side ranch home SW Harbor. Prime MDI locale

This comfortable home named the Autumn Lodge located in the lively picturesque village of Southwest Harbor can be enjoyed year round. Classic ranch home with open updated design and decorated with the colors of fall. Fully equipped kitchen with granite counters, dishwasher, and informal kitchen dining on the bar. Gas log fireplace. Private outdoor space. Harbor frontage on opposite side of the street. In town location walkable to restaurants & shops. Check out my other listing.

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.

CLEAN, spacious, each BR has private full bathroom

This 3 bedroom 3.5 bath home (each bedroom with its own full bathroom) is situated in a private, wooded setting on the edge of Southwest Harbor's bustling village. All on one level, it offers sophisticated yet comfortable furnishings in an open floor plan design. Each bedroom has a full bath. It’s close to several Acadia National Park access points (Long Pond and Echo Lake are both within a 5 minute drive). This home offers extra wide doorways accomodating those with mobility issues.

The Seamist Cottage - Converted Historic Barn

Cozy, fully converted historic barn within easy walking distance to the rocky shore of Bass Harbor, a busy lobstering port. An ideal, pet friendly, home base while exploring Acadia National Park. The Seamist is located on "the quietside" of the island. Six minutes from Southwest Harbor and thirty minutes to Bar Harbor, the Seamist also offers guests private hot tub access! Two guests maximum, not a suitable space for children. Please keep allergies in mind when booking. No smoking.

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.

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.

Hulls Cove Cottage

Settled right outside Hulls Cove Village and its entrance to Acadia National Park, this lovely, cozy cottage is minutes from downtown Bar Harbor and its shopping, restaurants, kayaking and other activities. A classic New England shingled cape, you'll feel right at home in the updated living space, with an upstairs queen bedroom, loft with twin beds, and private backyard. Centrally located to take advantage of everything Mt. Desert Island has to offer! Registration #VR1R25-047

Hot Tub Art Sail Loft. Swans Island

Experience the beauty of nature in this art lovers abode. The dynamic brushstrokes and colors create an atmosphere of tranquility, making it an ideal retreat for those seeking inspiration and a connection with nature. Just steps to fisherman’s cooperative with daily catch lobsters. Walk to the lighthouse or lay back in the hot tub after you drink your coffee in the widows walk with harbor views.

"Sweetwater"-- Bright, Airy, Modern

“Sweetwater,” named for the delightful view of an ocean inlet, is newly renovated in a Danish Modern style. It's ideally located in Southwest Harbor, a charming coastal town in Maine, on the “quiet side” of Mount Desert Island, home of Acadia National Park. The house has everything you need, whether you're seeking a family getaway or a place to gather with friends.