House holiday rentals in Southwest Harbor

A modern living area features a vaulted ceiling with wooden panels and large windows allowing natural light. A cozy seating arrangement with various chairs and a sectional sofa is complemented by a wood stove. A round marble dining table with a fruit bowl is positioned nearby.

5.0 out of 5 average rating, 101 reviews

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.

5.0 out of 5 average rating, 169 reviews

An aerial view captures the coastal cottage set on a granite ledge beside the Penobscot River. Surrounding trees in autumn hues frame the property, and the tranquil water reflects the colorful foliage, creating a serene natural setting.

Home in Hampden

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 10 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

5.0 out of 5 average rating, 10 reviews

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.

4.95 out of 5 average rating, 107 reviews

Tranquility Cottage (Year Round) & Cabin (May-Oct)

Peaceful & pet friendly acre near Acadia in natural, wooded setting. Fast WiFi, view to Ripples Pond (a wildlife sanctuary), & fenced in backyard. Big 1 bed cottage has comfy King mattress + 2 sleeper futons. The Cabin (only open May 1-Oct 31) has kitchenette, bathroom & Queen bed. A backyard path to hammock & chill spot by Ripples (view only, but 1/2 mile away is Long Pond for swimming, canoe/kayak rental). Grill. Firepit. Tranquility! NOTE: Cabin open May-Oct + has ceiling+box fans but no A/C

4.95 out of 5 average rating, 20 reviews

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.

5.0 out of 5 average rating, 13 reviews

Harbor Chalet Acadia-Hot Tub-Fireplace~Beach~Dock

Harborside Chalet 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.

The exterior of a unique home is presented, featuring a combination of grey shingles and blue siding. Colorful buoys are adorned on the facade, complemented by window boxes filled with greenery. A welcoming entrance is flanked by a bright flag, set amidst a wooded backdrop.

4.99 out of 5 average rating, 134 reviews

Southwest Harbor Hideaway in the Woods of Acadia

This eclectic buoy wonderland is the perfect hub for your vacation! Great for families & groups. 2 primary suites w/ king beds, king-bunk room & A/C throughout, nestled in the woods on the Quietside of Mount Desert Island! Amazing backyard entertaining area. Tons of amenities: kayaks, paddleboards, bikes, cornhole, & large firepit w/ firewood! Private yet convenient - close to the ocean, hikes, downtown SW Harbor, 5min to Acadia's Seawall Beach, Bass Harbor Lighthouse, Echo Lake Beach & more.

4.87 out of 5 average rating, 216 reviews

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.

The front porch of the house features rocking chairs and is shaded by large trees. An American flag is displayed prominently, and greenery surrounds the entrance. The porch is accessible from well-maintained steps leading to a lush, grassy yard.

5.0 out of 5 average rating, 78 reviews

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.

A charming cedar cottage is nestled among tall trees, featuring a spacious front porch. A stone pathway leads to the entrance, surrounded by lush greenery and natural landscaping. Solar panels are visibly integrated into the roof, highlighting a commitment to sustainability.

4.98 out of 5 average rating, 231 reviews

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.

The exterior of a renovated cottage is showcased, featuring a light grey facade with white trim. A welcoming front porch is furnished with two chairs, and a spacious lawn surrounds the house, complemented by mature trees and vibrant greenery.

4.92 out of 5 average rating, 130 reviews

Charming Cottage Near Acadia & Village

Freshly renovated home with modern amenities, including new appliances and furniture, and a cozy patio with a lawn for outdoor relaxation. Three bedrooms offer various sleeping arrangements, perfect for families. Situated in the quiet village of Northeast Harbor, it's a short walk to the ocean and downtown amenities like restaurants, bars, a gas station, and the grocery store. Acadia National Park trails are less than 5 minutes away by car, while Bar Harbor is a quick 20-minute drive.

4.95 out of 5 average rating, 327 reviews

A two-story post and beam house is set on a spacious green lawn, surrounded by trees and autumn foliage. The exterior features wooden siding with multiple windows, showcasing a blend of rustic charm and natural beauty.

Home in Swans Island

Hot Tub Time Machine

Step into a vibrant world with this collection of paintings that celebrate color and texture. Enjoy pristine beaches and forest and spread out in this 2600 sq ft house with cathedral ceilings, 2 fireplaces, sauna and well stocked kitchen. Explore the island and it's hikes and fine sand beaches or take a dip in the quarry. Discover a dramatic narrative with this striking home that juxtaposes nature and fantastic mythical creatures Please read “other details”, we are on an island.

Popular amenities for Southwest Harbor house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.71 out of 5 average rating, 51 reviews

An in-ground pool is surrounded by a concrete deck, featuring a roofed area with three bar stools. Lush greenery lines the perimeter, ensuring a private and peaceful environment. The clear blue water is inviting, ideal for summer relaxation and recreation.

Home in Tremont

Large MDI house w/pool perfect for groups+families

5.0 out of 5 average rating, 4 reviews

Bar Harbor, near Acadia with seasonal dock & pool

4.98 out of 5 average rating, 42 reviews

The outdoor area is illuminated by string lights, creating a warm ambiance around a fire pit. A tent shelters a picnic table, while lounge chairs invite relaxation. An above-ground pool is positioned in the background, surrounded by trees, enhancing the private setting.

Home in Trenton

Acadia get away.! With pool and hot tub

4.31 out of 5 average rating, 13 reviews

Home in Hancock

New Spacious Acadia Home with Pool!

An outdoor dining area is positioned on a spacious deck, featuring a long weathered table surrounded by ten wooden chairs. A large umbrella provides shade, while expansive views of the ocean and distant islands are visible in the background.

Home in Blue Hill

1798 - Spacious - Sleeps 10 - On Morgan Bay

The exterior of a modern two-story home is presented, featuring large windows across the upper level. A wooden deck with a railing extends from the front, while a garage door is situated below, showcasing a sleek design against a clear blue sky.

5.0 out of 5 average rating, 76 reviews

The Haven at Hadley's

4.83 out of 5 average rating, 18 reviews

Home in Winterport

Majestic Waterfront River Home Pet Friendly

4.89 out of 5 average rating, 28 reviews

A charming cape-style house is framed by lush greenery, showcasing a front porch with railings. An American flag is displayed prominently. The entrance is welcoming, with a few steps leading up to the porch, inviting guests to enjoy the peaceful country setting.

Home in Waltham

Higgins Retreat Quiet Country Cape

Weekly house rentals

4.88 out of 5 average rating, 78 reviews

Dirigo Haven | Sauna, Harbor, Acadia

A cozy outdoor seating area features five red Adirondack chairs arranged on a stone patio, surrounded by lush greenery. A picnic table sits nearby, providing a space for al fresco dining. The house, with a blend of wood and dark siding, is nestled among tall trees.

4.98 out of 5 average rating, 80 reviews

SW Harbor: Salt in the Pines-Modern, Magical Oasis

4.84 out of 5 average rating, 19 reviews

5 mins to Acadia and 5 min walk to town!

A fire pit surrounded by four white Adirondack chairs is situated on a grassy area. The water reflects the sky in the background, while trees line the shore, creating a serene setting for relaxation and outdoor gatherings.

5.0 out of 5 average rating, 22 reviews

Hard Aground - Ocean View - Pet Friendly! SWH

An aerial view captures the unique vertically built home, surrounded by dense greenery and overlooking Somes Sound. The tranquil waterfront is visible, with neighboring properties marked by patches of trees and shoreline, creating a serene and natural setting.

4.93 out of 5 average rating, 71 reviews

4 BR Waterfront Unique House + Dock! [Osprey Cove]

4.99 out of 5 average rating, 87 reviews

An open kitchen and living area is showcased, featuring large windows that allow natural light. A curved staircase, surrounded by a Maine poplar tree, leads to the upper level. Wooden accents provide a warm touch, with potted plants placed near the staircase.

Home in Tremont

Private, modern, minutes from Acadia.

A quaint cottage exterior is framed by surrounding trees, with a well-maintained grass area leading to the entrance. Large windows invite natural light, while a small deck can be seen on the side. The peaceful ocean view is visible in the background.

4.81 out of 5 average rating, 43 reviews

Charming Cottage with Ocean View

The charming cottage exterior is framed by lush greenery and ferns, creating a natural setting. A welcoming front porch features a decorative door and vibrant flower pot. Large windows allow for natural light, ensuring a bright entrance to the home.

5.0 out of 5 average rating, 4 reviews

The Elegant Somes Sound Bunkhouse

Private house rentals

5.0 out of 5 average rating, 45 reviews

An aerial view captures the waterfront cottage nestled among lush trees along the Bagaduce River. The expansive greenery surrounds the property, leading to serene water along the shore. The distant Blue Hill mountain is visible under a clear sky, providing a tranquil backdrop for this secluded retreat.

Home in Brooksville

Casa on the Bagaduce River

A classic two-story camp from 1915 is framed by lush greenery. The exterior features natural wood shingles and a gable roof. A welcoming porch with two chairs invites relaxation, while a gravel pathway leads through the garden, connecting visitors to the charming entrance.

5.0 out of 5 average rating, 20 reviews

Rustic Retreat on MDI

A dining area features a wooden table surrounded by four black chairs. Large windows are dressed with light curtains, allowing natural light to illuminate the space. An overhead light fixture with multiple bulbs creates a warm ambiance, complementing the modern kitchen in the background.

5.0 out of 5 average rating, 39 reviews

Sea Glass Cottage in Acadia

4.88 out of 5 average rating, 58 reviews

Renovated 3BR Home in Downtown SWH [Mariners Rest]

5.0 out of 5 average rating, 15 reviews

Captain Whitmore Cottage

4.98 out of 5 average rating, 62 reviews

BarHarbor Cedar Chalet - Ocean view- 10 min Acadia

5.0 out of 5 average rating, 10 reviews

Home in Winter Harbor

Silver Mist Cottage

The exterior of the house features a welcoming front porch with white railings, surrounded by well-maintained landscaping. Shrubs and small trees line the path, leading to the entrance framed by blue shutters. A sunny sky and a peaceful neighborhood ambiance are evident.