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Bailey Island vacation rentals

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Top-rated vacation rentals in Bailey Island

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

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Home in Harpswell

4.94 out of 5 average rating, 120 reviews

Brand new Scandinavian cottage: dock & kayaks!

Brand new architectural cottage and detached 'boathouse' with sweeping elevated ocean views both east and west, private waterfront lawns and deep water dock with kayaks. This property was built in 2020 so expect a fresh and clean experience on one of Harpswell's most private peninsulas. Watch the sunrise from the cantilevered 2nd floor deck, sit by the campfire on your private lawn oceanside, or walk down to the dock for a paddle in the west facing protected cove. The best of coastal Maine!

Cottage in Brunswick

5 out of 5 average rating, 150 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering property right on historic Route 24, a busy thoroughfare between Brunswick & the islands of Harpswell. All rooms have ocean views. There is a beach & the dock (May-Dec) is ideal for seasonal fishing, lounging & swimming. Check out our Insta @gurnetvillage for photos & calendar release dates

Cottage in Harpswell

4.97 out of 5 average rating, 108 reviews

Sea View Bungalow

Located in the center of beautiful Orrs Island, with unique ocean views a few steps in any direction. This ocean community is in the center of the Maine lobster fishing culture. Perfect location for ocean kayaking, canoeing or sailing. Just walking and enjoying the seacoast is the goal of many visitors. Internet may occasionally be spotty. Seafood abounds for eating out or bringing back to your cottage. One bed is a futon in the living area. Unfortunately, we can not accommodate pets.

Barn in Freeport

5 out of 5 average rating, 159 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Welcome to our spacious 1000 sq. ft. Maine barn apartment! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the private bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 374 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Tiny home in Bowdoinham

4.91 out of 5 average rating, 107 reviews

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

Home in Bath

4.9 out of 5 average rating, 319 reviews

Gorgeous Winter Studio on the Kennebec

Gorgeous riverside studio, the smaller of two AirBnB houses on the same property on the outskirts of beautiful and historic Bath, Maine. (The other, “Beautiful Summer River Retreat,” is a separate Airbnb rental.) Kitchenette, bathroom/shower, living room, and bedroom. Simple, modern decor. Close to great shops, restaurants, and beaches, and just a 20-minute drive from Bowdoin College. Adjacent to a boat launch, and a short walk from the Bath Marine Museum and a scenic dog park.

Treehouse in Georgetown

4.98 out of 5 average rating, 422 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Guesthouse in Brunswick

4.94 out of 5 average rating, 126 reviews

Modern Brunswick Cottage near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head and stocked with Aesop products for your use! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.

Guest suite in Freeport

4.97 out of 5 average rating, 147 reviews

Solar Suite surrounded by Nature

Solar suite on conservation property offers peaceful getaway. Large sitting room furnished with contemporary sofa, reading area, bedroom nook with natural latex Queen mattress on Japanese platform, kitchen island/toaster oven, mini fridge, dishes, silverware, linen napkins (please note this is not a full kitchen for preparing meals) private bath/shower. On the lower level of our home with private entrance. Cedar hot tub available.

Home in Harpswell

4.98 out of 5 average rating, 196 reviews

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

Guesthouse in Harpswell

4.95 out of 5 average rating, 453 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, spacious, colorful, comfy, bright! New king bed! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Popham Beach and Reid State Park with expansive beaches are 35 minutes or less away.

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Popular amenities for Bailey Island vacation rentals

Laptop-friendly workspace

Air conditioning

Bailey Island cottage rentals

Cottage in Scarborough

4.97 out of 5 average rating, 211 reviews

Bright, clean, private cottage near Higgins Beach!

Cottage in Saco

4.94 out of 5 average rating, 120 reviews

Bright & Cozy Beachside Cottage in Camp Ellis

Cottage in Naples

4.85 out of 5 average rating, 109 reviews

Winter Wonderland at Turtle Lane Cottage

Cottage in Saco

4.93 out of 5 average rating, 375 reviews

Deja Blue~Guest Beach House

Cottage in Portland

4.96 out of 5 average rating, 198 reviews

4br2ba House+parking@PeacefulOasis on Munjoy Hill

Cottage in Saint George

4.95 out of 5 average rating, 220 reviews

Hidden Haven A Rustic Retreat In St. George, Maine

Cottage in Topsham

4.94 out of 5 average rating, 245 reviews

Cozy waterfront home on Merrymeeting Bay.

Cottage in Friendship

4.91 out of 5 average rating, 256 reviews

Our charming,oceanfront, Bradford point cottage

Other great vacation rentals in Bailey Island

Cottage in Harpswell

4.96 out of 5 average rating, 45 reviews

Old fashion neighborhood near the water.

Guest suite in Portland

4.99 out of 5 average rating, 307 reviews

Sunny West End Guest Suite w/Harbor Views and Pool

Cabin in Harpswell

5 out of 5 average rating, 21 reviews

Waterledge Cottage - Orrs Island, Maine

Guesthouse in Freeport

5 out of 5 average rating, 55 reviews

Mast Landing Cottage

Home in Harpswell

5 out of 5 average rating, 13 reviews

Family Tides-Ocean Views, Spacious, Lovely Home

Guesthouse in Windham

4.99 out of 5 average rating, 251 reviews

Cottage on Black Brook Preserve

Cabin in Oxford

4.94 out of 5 average rating, 125 reviews

Thompson Lake, Maine. discount winter rate Cottage

Guesthouse in Boothbay Harbor

5 out of 5 average rating, 249 reviews

The Sparrow’s Nest Charming Country Cottage

Destinations to explore