Vacation rentals in Westport Island

4.91 out of 5 average rating, 169 reviews

A modern A-frame structure is nestled within a wooded setting, featuring a dark exterior with wooden accents. Adjacent, a spacious gazebo is set on a gravel patio, furnished with a dining table and a comfortable seating area, surrounded by trees offering a sense of privacy.

Tiny home in Wiscasset

Tiny A-Frame Romantic Getaway

Camp Lupine is a brand new Luxury 400 sq ft Tiny A-Frame tucked away on a private wooded lot with a small stream just a quarter mile off Coastal Route 1. With Historic Wiscasset, Booth Bay, Bath, Freeport, and Portland all at your fingertips, it’s the perfect romantic getaway. Spend your days exploring coastal Maine and your nights soaking in the hot tub with a glass of Malbec. Stay for a while and explore the growing restaurant scene in Wiscasset and the entire Midcoast region. See you soon!

The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.

4.99 out of 5 average rating, 139 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

4.87 out of 5 average rating, 100 reviews

A spacious home is depicted, featuring a neutral exterior with a sloped roof. Lush green trees surround the property, complementing the stone pathway that leads to the entrance. Large windows provide natural light, and manicured shrubs frame the front yard.

Guesthouse in Wiscasset

Private & Peaceful Guest Suite With AC

Welcome to MJ Castle! Imagine waking up to a beautiful sunrise, bird chirping, quiet and peaceful environment. Whether you're traveling through or visiting family in town, this is a perfect place to Stay. Enjoy our guest suite in this beautiful design home. Our guest suite equipped with brand new composite deck, brand new furniture, along with other amenities. This property located on a quiet road right off Route 1, Closed to a boat launch and Downtown Wiscasset. More pictures coming soon!

4.99 out of 5 average rating, 131 reviews

A waterfront view is captured from a deck, showcasing calm waters surrounded by a lush landscape of colorful trees. The bright blue sky reflects on the surface of the creek, while greenery provides a serene foreground.

Home in Bath

Waterfront Farmhouse with Modern Flair!

On the shores of Winnegance Creek in Bath, Maine—one of America’s best small towns—this 19th-century farmhouse has been completely renovated. Boasting waterfront views and sitting on more than an acre of land, opportunities for recreation and relaxation abound. Enjoy the outdoor deck, fire up the grill, visit the beach or the farmers market, explore the area via kayak, stargaze—so much to do! Not to mention shopping, restaurants, and all that downtown Bath and midcoast Maine have to offer!

A tranquil scene captures a person walking along a wooden dock extending into calm waters. The surface reflects the warm hues of sunset, while trees frame the distant shoreline, creating a serene backdrop to the peaceful landscape.

4.91 out of 5 average rating, 22 reviews

Hall Bay Haven

This brand-new waterfront cottage has it all! Killer views of the water from the large deck, screen porch, or through the wall of windows in the vaulted living area. Well-equipped gourmet kitchen, tiled bathrooms, outdoor shower, ramp and float, canoe and kayak, and much more. Convenient to Bath, Five Islands, Reid State Park. Walking distance to Robinhood/Derecktor Marina, Osprey Restaurant, and Robinhood Free Meeting House. Two queen beds and a very comfortable queen sleeper in LR.

Farm stay in Westport Island

The rustic exterior of the historic retreat features a weathered brown shingle facade and a vibrant red front door. A spacious deck extends towards the water, surrounded by greenery and providing a serene view of the tidal Sheepscot River at sunset.

The Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

4.84 out of 5 average rating, 137 reviews

4.97 out of 5 average rating, 381 reviews

The exterior of the cottage features a large screened-in porch framed by tall trees. A pathway leads to the entrance, while colorful shrubs and a pumpkin add seasonal charm. The serene waters of the Sheepscot River are visible in the background.

Cottage in Edgecomb

Charming Cottage With Spectacular Water View

Find peace and serenity as you gaze at the glistening waters of the Sheepscot River. Our property sitting on Davis Island in Edgecomb, Maine overlooks the quaint town of Wiscasset, providing a calm atmosphere, stunning evening sunsets, and panoramic views. Located within the Sheepscot Harbour Village Resort, you are in a prime location to have access to local shops, antique markets, and restaurants. Take a stroll down to the Pier where you can experience the water up close.

4.95 out of 5 average rating, 112 reviews

A wooden dining table is set by large windows, offering views of the water and surrounding trees. A blue bowl sits at the center, complemented by placemats in soft blue tones. Natural light fills the space, highlighting the warm wooden floor.

Apartment in Wiscasset

Panoramic Water Views on the Sheepscot

From our living room a wall of windows take in the expansive views of Barter's Island upward to the ocean. Relax on the sunny deck, listen to the birds and lobster boats and watch the seals on the ledge at low tide. Take a walk for breathtaking scenic views of the Sheepscott river. Bring your books, bikes and kayaks. Westport Island offers several preserves for hiking, a local brewery and is a central location to visit many nearby midcoast sights and activities.

5.0 out of 5 average rating, 29 reviews

Home in Wiscasset

Cozy Midcoast Island Cottage

Unplug, unwind, and experience the true essence of Midcoast Maine. Nestled in the quiet woods of historic Westport Island, our cozy cottage offers a peaceful sanctuary surrounded by tidal inlets, towering pines, and abundant wildlife. Enjoy complete privacy with easy bridge access to the mainland. The perfect balance of seclusion and coastal convenience. Midcoast Maine harbors, lighthouses, beaches, and local seafood spots are just a short drive away.

The rocky coast is lined with spruce trees, showcasing natural contours along the shoreline. Calm blue waters gently lap against the rocks, while a clear sky enhances the scenic view. A few homes are nestled among the trees, blending harmoniously with the coastal landscape.

5.0 out of 5 average rating, 128 reviews

Perched atop the Coast of the Atlantic Ocean

Enjoy sweeping vistas of the Atlantic Ocean from this 2002 home perched among spruce trees above the rocky coast. Watch for bald eagles and seals. Fall asleep to the sound of crashing waves. Walk down to the edge of the ocean to lounge or picnic. Walk 6 minutes or drive the 0.1 miles to the park entrance. Hike the Little River Trail. The house has vaulted ceilings, panoramic views, fully equipped kitchen, and whirlpool bath.

4.98 out of 5 average rating, 60 reviews

A modern kitchen features light-colored cabinetry and a large wooden island with seating for three. Stainless steel appliances, including a refrigerator and oven, complement the design. Natural light enters through a nearby window, illuminating the granite countertops and open shelving displaying white dishes.

Home in Boothbay

Beautiful modern cabin

Minutes from the Maine Botanical Gardens and Gardens Aglow! Relax with the whole family at this peaceful new cabin on Barters Island near Boothbay Harbor, Maine. Modern amenities meet rustic charm, ensuring a comfortable stay. Expansive windows bathe the interior in natural light, accentuating the hardwood floors and contemporary décor. With easy access to the beautiful Maine coast, this Barters Island cabin is the ideal serene retreat.

4.92 out of 5 average rating, 241 reviews

A two-story home is set on a spacious, grassy lot surrounded by trees. A paved driveway leads to the front, where a walkway is bordered by shrubs and greenery. A serene, wooded backdrop completes the peaceful atmosphere of the property.

Guest suite in Woolwich

Private Guest Apartment with separate entrance.

Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking. sitting room with a dining table that looks out onto the deck, queen bedroom, private bathroom with jetted tub and separate shower, fully equipped kitchenette; NEW FURNACE-quiet and efficient.

Popular amenities for Westport Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Westport Island

4.97 out of 5 average rating, 38 reviews

A quaint white cottage is nestled among lush greenery, surrounded by colorful blooming flowers. A small deck is visible in front, furnished with two chairs, offering a serene spot to enjoy the natural surroundings.

Home in Boothbay

Cozy cottage with dock on river

4.84 out of 5 average rating, 147 reviews

A modern exterior of a green metal-clad house is shown, featuring a sloped roof and a welcoming front porch with steps. Large windows provide natural light, while surrounding trees create a serene environment. A paved driveway is visible in front.

Home in Wiscasset

Perfectly located in the heart of Midcoast Maine!

4.82 out of 5 average rating, 66 reviews

A bright and airy living room features a large sofa paired with a lounge chair, centered around a wooden coffee table. Sunlight streams through multiple windows, enhancing the natural wood paneling and flooring. A TV is positioned on a cabinet, with a propane stove visible in the corner.

Cottage in Edgecomb

River View Casita

4.83 out of 5 average rating, 18 reviews

Home in Boothbay

The Nest on Sawyers Island

4.99 out of 5 average rating, 81 reviews

A sunlit sitting area features large glass doors that open to a scenic outdoor view. A wooden dining table is accompanied by four chairs. Vibrant sunflowers in a vase adorn the table, while a plush sofa with a patterned throw is positioned nearby.

Apartment in Wiscasset

Bright apt on quiet Westport Isle with river view

An outdoor deck is furnished with a patterned tablecloth covering a dining table accompanied by six wooden chairs. Two lounge chairs are positioned nearby, offering views of the calm water, boats, and greenery. A flowering centerpiece adds a touch of color to the table.

5.0 out of 5 average rating, 30 reviews

Five Islands Waterfront Retreat

4.94 out of 5 average rating, 51 reviews

A serene view of a tranquil lake is framed by tall trees, their green leaves softly rustling in the breeze. The still water reflects the surrounding nature, creating a peaceful atmosphere ideal for relaxation. Sunlight filters through the branches, illuminating the scene.

Home in Arrowsic

Waterfront Guest House in Coastal Maine