Vacation rentals in Westport Island

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Top-rated vacation rentals in Westport Island

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Guest favorite
The serene view showcases a sunrise over the calm waters of the Sasanoa River, reflecting golden hues. Lush greenery frames the scene, while the distant treeline adds depth to the landscape. Soft clouds linger above, enhancing the tranquil atmosphere of the setting.
Cottage in Woolwich
4.91 out of 5 average rating, 206 reviews

Pet Friendly Audubon Bring Your Fishing Gear!

Enjoy the view from this wonderful 1940's waterfront cottage on the Sasanoa River in Woolwich. From here access Reid or Popham Beach State Parks with ease. Visit Maine Maritime museum in Bath, the "City of Ships." Head to Portland for a night out. Just relax and watch the seals, osprey and eagles. Rent a boat to enjoy all this extremely special waterway has to offer. Around the corner is the Kennebec River and Merrymeeting Bay, to the south you'll discover Phippsburg and historical Fort Popham.

Guest favorite
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
4.91 out of 5 average rating, 157 reviews

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!

Top guest favorite
A bright eat-in kitchen area features a small wooden table with two chairs. Natural light streams through large windows, providing a view of the lush garden. A washer and dryer are positioned nearby, enhancing the functionality of the space.
Apartment in Bath
4.97 out of 5 average rating, 187 reviews

1820s Maine Cottage with Garden

Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

Top guest favorite
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.
Home in Georgetown
4.99 out of 5 average rating, 122 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.

Top guest favorite
A view of the Sheepscot River is framed by trees, showcasing a wooden dock extending into the water. The scene includes a chain-link fence and a mix of greenery, offering a serene setting under partially cloudy skies.
Apartment in Edgecomb
5 out of 5 average rating, 22 reviews

Guesthouse on Sheepscot River

Newly renovated one bedroom guest house in mid coast Maine located on a quiet street just off route #1 in Edgecomb, Maine. Sit on the patio and enjoy gorgeous sunsets overlooking the Sheepscot river. This is an extremely quiet area that is 15 minutes to Boothbay Harbor, an hour to Camden to the north and an hour to Portland to the south. The immediate area offers fabulous local seafood, fantastic botanical gardens, and quant little villages like Damariscotta, Wiscassett and Boothbay.

Guest favorite
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.
Farm stay in Westport Island
4.84 out of 5 average rating, 134 reviews

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.

Guest favorite
The front entrance showcases a vibrant red door framed by two sconces, inviting guests inside. Steps lead up to a spacious deck, which is flanked by decorative flower pots. The house features a classic shingle exterior, accented by charming dormer windows.
Home in Boothbay Harbor
4.92 out of 5 average rating, 159 reviews

Renovated home with amazing waterfront views

Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

Top guest favorite
A charming house with a light blue exterior is surrounded by a lush garden. Colorful flowers, including purple irises, bloom in front of the stone wall. Mature trees provide greenery in the background, creating a serene and inviting outdoor space.
Guest suite in Wiscasset
5 out of 5 average rating, 36 reviews

Birch Point at Cushman Cove- Private/Entire Suite

Mid-Coast, Maine! Kick back and relax in this calm, comfortable & stylish space. We're just a short drive into town... 'Prettiest Village in Maine' they say!. Located just off Route 1, an ideal location to explore all that Mid-Coast has to offer; charming towns and villages, spectacular beaches and vistas, galleries & museums, restaurants, farmers markets.....all within reasonable driving times. And don't miss Boothbay Botanical Gardens.... sure to delight your senses!

Top guest favorite
Cabin in Georgetown
5 out of 5 average rating, 191 reviews

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

Top guest favorite
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
4.92 out of 5 average rating, 227 reviews

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.

Guest favorite
A three-story home is set amidst lush greenery, featuring a combination of light gray siding and a unique stone chimney. A spacious deck with a screened-in area is visible, along with a series of wooden steps leading to the front entryway.
Home in Edgecomb
5 out of 5 average rating, 6 reviews

Peaceful Rural Riverfront | 4BR | Wildlife |Dock

Welcome to your secluded riverfront retreat in Mid coast Maine, managed by Rocky Coast Rentals—a peaceful escape designed for families and creatives alike. This 4BR/3BA home features stunning water views, a private dock with deep water access, and spacious, comfortable living areas surrounded by nature. Perfect for gathering, unwinding, and finding inspiration, with easy access to nearby coastal towns and attractions.

Top guest favorite
The cottage exterior features light-colored siding and a distinctive steeply pitched roof with a prominent window above the entrance. Double doors framed by a large glass panel invite visitors inside, surrounded by lush greenery and flowering shrubs.
Guesthouse in Boothbay Harbor
5 out of 5 average rating, 266 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.

Popular amenities for Westport Island vacation rentals

When is the best time to visit Westport Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,666 GYDG$41,642 GYDG$40,805 GYDG$55,871 GYDG$42,479 GYDG$46,664 GYDG$47,082 GYDG$52,313 GYDG$52,313 GYDG$51,267 GYDG$53,360 GYDG$51,267 GYD
Avg. temp-6°C-5°C0°C6°C12°C17°C21°C20°C16°C9°C3°C-2°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Westport Island?

    Westport Island has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Westport Island?

    Experience the best of Westport Island with our cottage rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Westport Island?

    Four-legged friends are welcome in Westport Island. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Westport Island?

    Yes! Work meets play with ease at over 30 vacation rentals in Westport Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do hotel rentals in Westport Island have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Westport Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westport Island have a kitchen?

    Absolutely! We offer over 40 house rentals with a kitchen in Westport Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westport Island have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Westport Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westport Island have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Westport Island. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Westport Island

  • Total vacation rentals

    Explore 90 vacation rentals in Westport Island

  • Nightly prices starting at

    Westport Island vacation rentals start at G$14,648 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,580 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Westport Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Westport Island rentals

  • 4.9 Average rating

    Westport Island stays are highly rated by guests—averaging 4.9 out of 5!

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