Holiday rentals with a kayak in Boothbay Harbor

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Boothbay Harbor

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

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Top guest favourite
The A-Frame cabin is surrounded by tall trees and a snowy landscape, showcasing large windows that reflect warm light. A wraparound deck features outdoor seating, inviting relaxation in a serene wooded setting at dusk.
Cabin in Chesterville
4.99 out of 5 average rating, 171 reviews

Off-Grid Escape. Wood Fired Hot Tub, Snowshoes

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Top guest favourite
A serene waterfront scene captures the sun setting over a calm bay, with reflections in the water. In the foreground, tall grasses and wildflowers frame the image, leading to a dock with two Adirondack chairs arranged for relaxation.
Cottage in South Hiram
4.93 out of 5 average rating, 280 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Top guest favourite
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, 107 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.

Guest favourite
A modern tiny house is nestled among tall trees, showcasing two large glass walls that allow sunlight to stream inside. The cabin is elevated on stilts, with a snowy landscape surrounding it, creating a serene and private retreat in nature.
Tiny home in Jay
4.93 out of 5 average rating, 261 reviews

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $89.

Top guest favourite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 198 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, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favourite
A serene waterfront view captures calm waters reflecting the sky and surrounding landscape. Lush greenery is visible along the shore, while scattered clouds drift across the blue sky. The tranquil scene invites relaxation and appreciation of nature.
Home in Newcastle
4.99 out of 5 average rating, 179 reviews

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

Top guest favourite
A cozy cabin is nestled within a forest, featuring a spacious covered porch and steps leading up to it. Seating is arranged around a fire pit in the foreground, with several black Adirondack chairs placed on a gravel surface, surrounded by lush greenery.
Cabin in Georgetown
4.88 out of 5 average rating, 139 reviews

Cozy log cabin on private pond, near Reid St Park!

Winter or summer, the Little River Retreat will help you step away from the world - but still be minutes from Reid State Park, Five Islands Lobster, the Georgetown General Store, and the rugged beauty of Midcoast Maine. This is our family camp, with our own books, games, and “vibe”. It is not a hotel, and some things may not be “industry standard”. We love the unique charm of this space and place, and many repeat guests do too. We hope you will treasure (and care for it) as we do!

Guest favourite
An airy cabin interior features wood beams and a large sliding glass door, providing access to a deck and surrounding greenery. A small dining area with a table and two chairs is visible alongside a well-equipped kitchen area, complete with modern appliances.
Tiny home in Bowdoinham
4.91 out of 5 average rating, 140 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.

Top guest favourite
The exterior of the cottage features a welcoming wooden deck with seating underneath a blue umbrella, surrounded by green grass and blooming flowers. A fire pit and two Adirondack chairs are positioned on the lawn, providing a cozy outdoor gathering space.
Cottage in Boothbay
5 out of 5 average rating, 130 reviews

Cottage in the woods on Ocean Point

Secluded getaway in the woods close enough to see and hear the ocean and catch amazing sunsets. Charming 1BR + Loft, 1BA cottage situated among an acre of Ocean Point fir trees providing privacy and a quiet get away. Less than 100yd walk to the shore, beach and path at Grimes Cove, Ocean Point Inn Restaurant & Bar, and daily activities at the community "casino" building with playground, tennis, pickle ball, basketball, and Sunday softball. Harbor is 20 mins away for exploring.

Guest favourite
The two elevated structures of the tree dwelling are connected by a rope bridge, surrounded by lush green trees. Natural materials are utilized in the design, which includes a balcony and multiple levels that create a unique, inviting silhouette against the forest backdrop.
Treehouse in Georgetown
4.98 out of 5 average rating, 450 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!).

Guest favourite
A serene landscape captures a vibrant sunset reflected on calm water. The sky displays shades of orange and pink, blending into deep purple hues, while the silhouette of trees lines the horizon. The tranquil scene conveys a peaceful natural setting.
Loft in West Gardiner
4.96 out of 5 average rating, 216 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Top guest favourite
A contemporary yurt is nestled among snow-dusted trees, surrounded by a blanket of white snow. A spacious deck extends from the yurt, providing access to the inviting living space. The serene winter landscape and trees enhance the retreat's secluded charm.
Yurt in Appleton
4.94 out of 5 average rating, 334 reviews

SNOW SWEET, A Yurt for All Seasons

Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Popular amenities for kayak rentals in Boothbay Harbor

Quick stats about holiday rentals with a kayak in Boothbay Harbor

  • Total holiday rentals

    Explore 40 holiday rentals in Boothbay Harbor

  • Nightly prices starting at

    Boothbay Harbor holiday rentals start at $154 SGD per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Boothbay Harbor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Boothbay Harbor rentals

  • 4.9 Average rating

    Boothbay Harbor stays are highly rated by guests – averaging 4.9 out of 5!

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