Vacation rentals in Westport Island

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Quick stats about vacation rentals in Westport Island

  • Total vacation rentals

    Explore 100 vacation rentals in Westport Island

  • Nightly prices starting at

    Westport Island vacation rentals start at G$16,732 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    70 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 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!

Top-rated vacation rentals in Westport Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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, 169 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!

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Top guest favorite
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
4.99 out of 5 average rating, 131 reviews

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!

FamilyLocationHospitality

Guest favorite
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.
Home in Georgetown
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.

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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, 137 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.

LocationFamilyTV

Guest favorite
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
4.97 out of 5 average rating, 381 reviews

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.

ValueFamilyComfort

Guest favorite
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
4.95 out of 5 average rating, 112 reviews

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.

LocationValueNearby

Guest favorite
The living area features a soft teal sofa positioned across from a wooden coffee table. A rug covers the floor, and natural light enters through large windows adorned with white curtains. A small lamp and a potted plant add to the welcoming ambiance.
Home in Bath
4.95 out of 5 average rating, 128 reviews

The Cottage

Welcome to The Cottage—your cozy getaway in the heart of Bath, Maine! Perfectly situated near charming coastal towns, beautiful beaches, and scenic hiking trails, this retreat offers a comfy living area, fully equipped kitchen, and four inviting bedrooms. Sip your morning coffee from the sunny dining room window seat, or wind down by the fire pit out front. Note: The Cottage is attached to the owner’s home, but you’ll have full privacy throughout your stay.

ValueFamilyGetting around

Top guest favorite
Home in Wiscasset
5.0 out of 5 average rating, 29 reviews

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.

LocationFamilyComfort

Top guest favorite
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.
Home in Georgetown
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.

LocationFamilyAccuracy

Top guest favorite
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
4.98 out of 5 average rating, 60 reviews

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.

LocationFamilyTV

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, 240 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.

LocationFamilyCheckout

Top guest favorite
The exterior of a rustic mid-century cabin is framed by lush greenery, featuring a screened-in porch and wooden deck. Stairs lead up to the entrance, and natural stone accents create a seamless blend with the surrounding landscape.
Cabin in Boothbay Harbor
4.98 out of 5 average rating, 284 reviews

Lakeside 3 BR Cabin in Boothbay Harbor

This swanky mid-60's cabin sits on a hill overlooking West Harbor pond in the town of Boothbay Harbor. It offers privacy yet is close to everything downtown Boothbay Harbor has to offer. It is great for couples, solo adventurers, business travelers and families (with kids), and large enough to accommodate bigger groups. If you would like to bring along your canine pal feel free, they are welcome (sorry no cats).

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Popular amenities for Westport Island vacation rentals

When is the best time to visit Westport Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,646 GYDG$41,620 GYDG$40,784 GYDG$33,254 GYDG$53,332 GYDG$50,404 GYDG$47,058 GYDG$52,287 GYDG$52,287 GYDG$51,241 GYDG$53,332 GYDG$51,241 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 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Westport Island with our hotel rentals, starting at about $270 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 40 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 50 house rentals with a kitchen in Westport Island. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Westport Island have wifi?

    Absolutely! We offer over 10 hotel 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 50 house rentals with free parking in Westport Island. Enjoy a tailored experience with all the comforts you desire.