Holiday rentals with a kayak in Waldoboro

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Waldoboro

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

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Top Guest favourite

Home in Augusta

4.95 out of 5 average rating, 147 reviews

Lakefront: Private Hot Tub, Sauna & Free Massages!

Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

Guest favourite

Cottage in Topsham

4.93 out of 5 average rating, 249 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.

Guest favourite

Guest suite in Orrington

4.97 out of 5 average rating, 110 reviews

Lake front luxury retreat with an Island View

Indulge in lakeside luxury at our modern, waterfront studio retreat! Perched on the water's edge, this pet-friendly haven offers: Private dock and lake access · Spa-inspired indoor and outdoor showers · Cozy fire pit for a relaxing movie night under the stars · Unbeatable views and direct access to the lake for swimming & soaking up the sun · The serene sounds of loons and unforgettable memories to cherish. A short drive from town, experience the best of Maine living in style and tranquility.

Guest favourite

Home in Bucksport

4.92 out of 5 average rating, 100 reviews

Maine Wilderness Oasis: Hike Swim Kayak Fish

Take it easy at this unique getaway. Spend your days hiking the backyard trails (25 acres behind the house!), swimming or paddle boarding on the lake with a private dock (lake is a 2 minute walk down the driveway!), or traveling to near by coastal towns like Bar Harbor (Bucksport was voted #1 small coastal town in USA!). For dinner, stop by one of the lobster shacks just down the road to bring home your fresh Maine lobster! Come and disconnect (or stay connected if you’re working remotely!).

Top Guest favourite

Home in Bath

5 out of 5 average rating, 101 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!

Guest favourite

Home in Litchfield

4.92 out of 5 average rating, 135 reviews

Beautiful lake house on Tacoma Lakes near Coast

Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

Superhost

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!

Top Guest favourite

Home in Newcastle

4.99 out of 5 average rating, 156 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!

Guest favourite

Boat in Damariscotta

4.9 out of 5 average rating, 125 reviews

Nebi—Private Yacht on Scenic Damariscotta River

With warm wood interior, Nebi has the comfort of a home and a 360-degree view of the tidal Damariscotta River. Experience a unique Maine adventure, swim right off the boat, or paddle the inclusive kayaks downriver to view everything from seals to ospreys and oyster farms. The quaint twin villages of Damariscotta - Newcastle are a 2-minute stroll away from the private marina with charming restaurants, galleries and a short drive to gorgeous lighthouses, walking trails and beaches.

Top Guest favourite

Guesthouse in Penobscot

4.97 out of 5 average rating, 212 reviews

Sea Pearl

This is a Water Front property, unique and tranquil getaway. Newly renovated 2025, this is a perfect spot for your serious fun. Located on water in Penobscot. Bird watchers take notice, watch the eagles soar over head out your door, visit the many islands & see the Puffins, Whale watch. Lots to do kayaking, hiking and lot more! Or just relax in a stunning natural setting on the hammock under the apple trees. Just a short drive to Acadia National Park & Bar Harbor. See you soon.

Guest favourite

Home in Surry

4.93 out of 5 average rating, 30 reviews

Lakeside Home Close To Acadia National Park

Relax at this lake front home on Patten Pond. Enjoy your days relaxing by the water, kayak or canoe to a nearby sand beach, play yard games or hang out by one of 3 the fire pits on property. Not In the mood to paddle… the nearby swim hole is a half-mile walk away. Visit nearby Acadia National Park in Bar Harbor for hiking, biking, ocean beaches restaurants and shopping. Or visit Ellsworth for all your shopping needs and visit one of the many wonderful restaurants in town

Top Guest favourite

Island in Monmouth

4.98 out of 5 average rating, 229 reviews

Naughty Dog Private Island Log Cabin

Be all alone on this remote island with 1400 acres of Annabessacook Lake as your backyard. It's the Micro Island featured in Jon B. 2022 videos. Enjoy pristine surroundings, a rustic, off-the-grid log cabin, with solar lighting and a hot shower. Swimming, boating, fishing, birding, and relaxing by the fire - do it all (or not). Prepare for adventure! Pack light: Bring your vacay clothes, pups, favorite food, & be ready for a blissful, private island.