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Holiday rentals with a kayak in Harpswell

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Quick stats about holiday rentals with a kayak in Harpswell

  • Total holiday rentals

    Explore 50 holiday rentals in Harpswell

  • Nightly prices starting at

    Harpswell holiday rentals start at €78 per night before taxes and fees

  • Verified guest reviews

    Over 1,940 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Harpswell holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Harpswell rentals

  • 4.9 Average rating

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

Top-rated rentals with kayak in Harpswell

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

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Top guest favourite
An aerial view showcases the lush greenery of the property, framed by the coastline and tranquil waters of Cape Porpoise. The landscape reveals homes, docks, and boats dotting the cove, all under a bright sky with scattered clouds.
Home in Kennebunkport

Luxurious 5 bedroom on the ocean, w/ dock & kayaks

Historic 1735 home on a spacious one-acre property overlooking the ocean. Enjoy swimming from the dock in Cape Porpoise’s protected cove. Two kayaks provided for exploring the lighthouse & picnicking on nearby islands. Stroll past picturesque lobster boats to the town pier, where restaurants serve fresh local lobster & drinks. Walk to morning coffee, pastries, a local grocery store, athe renowned Nunan’s Lobster Hut. Just two miles from Kennebunkport and a nine-minute drive to Goose Rocks Beach.

4.97 out of 5 average rating, 150 reviews
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

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.

4.99 out of 5 average rating, 139 reviews
Top guest favourite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

4.91 out of 5 average rating, 602 reviews
Top guest favourite
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

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!

4.99 out of 5 average rating, 131 reviews
Guest favourite
A bright living area features a wooden floor and a cozy, gray sofa. A blue writing desk is positioned beside a window, adorned with decorative bookshelves and plants. A vintage-style wood stove is set against a brick wall, with warm light enhancing the inviting atmosphere.
Home in Freeport

Charming Historic Freeport House

Bring the whole family to this historic house just minutes from downtown Freeport and the LL Bean flagship stores. The cozy central kitchen and dining are flanked by two separate living rooms making plenty of room for fun and relaxation! With two twin beds, toddler bed and full-sized crib we can accomodate any family. Catch glimpses of the Harraseeket River from this updated 1840s home on a half acre. A wonderful jumping off point for both Portland and the natural beauty of Mid-coast Maine!

4.88 out of 5 average rating, 111 reviews
Guest favourite
Four wooden lounge chairs are arranged around a small table on a grassy lawn, overlooking a rocky shoreline. The calm ocean stretches into the distance, framed by a clear sky with soft clouds.
Home in Harpswell

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!

4.93 out of 5 average rating, 162 reviews
Top guest favourite
The image captures a serene riverside scene along the New Meadows River during sunset. Calm waters reflect the clear blue sky, while trees line the banks. Nearby, natural elements like rocky shores and patches of snow create a peaceful outdoor setting.
Cottage in West Bath

Coastal Waterfront Cottage in West Bath

***Please Message me to ask about possible discounts and length of stay minimums.*** 4 season home right on the waters edge on New Meadows River in West Bath sits this newly remodeled home. Fully furnished and includes a Minisplit Heat Pump/ AC, and Propane fireplace. Great location as it is on a dead end road that is just minutes to shopping, restaurants, etc. Incredible spot to watch the boats come and go as Sawyer park boat launch as well as the town boat launch are right in view.

4.93 out of 5 average rating, 135 reviews
Guest favourite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

4.97 out of 5 average rating, 197 reviews
Guest favourite
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

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.

4.84 out of 5 average rating, 137 reviews
Top guest favourite
An airy living space is highlighted by tall windows that bring in natural light and showcase views of the surrounding trees. A large sectional sofa faces a flat-screen TV, complemented by a wood stove for warmth. A dining area is visible in the background.
Home in Freeport

Waterfront 5 BR Home | On Casco Bay in Freeport

Spacious waterfront 5BR coastal retreat on Harraseeket Cove and South Freeport Harbor, perfect for kayaking, wildlife, and relaxing coastal Maine getaways. Set on 3.5 private wooded acres, the home features fast WiFi, smart TVs, outdoor dining, grills, firepit, kayaks, and peaceful water views throughout the property. Enjoy the tranquility of Maine’s coast while being only 3 minutes from Freeport’s shops, restaurants, breweries, and LLBean, with Wolfe’s Neck Woods State Park nearby.

4.96 out of 5 average rating, 145 reviews
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

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!

4.88 out of 5 average rating, 163 reviews
Guest favourite
The tree dwelling is elevated among sturdy trees, featuring a wraparound balcony surrounded by foliage. Large windows invite natural light, offering views of the lush surroundings. A rope bridge connects to another elevated structure, enhancing the unique treehouse experience.
Treehouse in Georgetown

Modern Treehouse 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!).

4.98 out of 5 average rating, 467 reviews

Popular amenities for kayak rentals in Harpswell

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Top guest favourite
Two wooden chairs are situated on a dock overlooking a calm pond surrounded by dense trees. The water reflects the sky and greenery, creating a serene backdrop. A sense of tranquility is conveyed through the peaceful atmosphere of the natural setting.
Home in Oxford

Mirror Pond Cottage

4.92 out of 5 average rating, 146 reviews
Top guest favourite
Home in Oxford

The Modern Lakehouse

5.0 out of 5 average rating, 245 reviews
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

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

4.98 out of 5 average rating, 210 reviews
Top guest favourite
A wooden dock extends into calm water, reflecting the clear blue sky and surrounding greenery. Trees line the shore, creating a serene backdrop for peaceful moments by the water.
Home in Friendship

Maine Waterfront Hideaway

4.96 out of 5 average rating, 130 reviews
Guest favourite
A serene view of a lake at sunset is presented, showcasing soft hues of orange, pink, and purple reflected on the water. Silhouettes of trees line the shore, while the calm surface creates gentle ripples, inviting relaxation and contemplation.
Home in Manchester

Lakeside retreat on quiet cove on Cobbessee Lake!

4.85 out of 5 average rating, 112 reviews
Top guest favourite
A circle of adirondack chairs surrounds a fire pit, set on grassy ground. Tall trees frame the view of the lake, where a serene sunset casts soft colors on the water. A dock can be seen in the distance, contributing to a tranquil outdoor space.
Home in Poland

Sunset Cove I

4.92 out of 5 average rating, 111 reviews
Top guest favourite
A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.
Home in Windham

Waterfront Gem walkable to Restaurants!

4.96 out of 5 average rating, 202 reviews
Top guest favourite
The lakefront property is nestled among trees, showcasing a charming house with large windows and a deck. A private dock extends into the calm water, providing space for seating. A sandy beach area leads to the water's edge, creating a serene natural setting.
Home in Limerick

Waterfront, Wood stove & Private beach, Solo Stove

5.0 out of 5 average rating, 142 reviews

Cottage rentals with a kayak

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 Topsham

Cozy waterfront home on Merrymeeting Bay.

4.93 out of 5 average rating, 302 reviews
Guest favourite
A cozy cottage exterior is depicted, featuring white siding and a green roof. A screened-in porch with comfortable seating is prominently displayed, along with a wooden entrance staircase. The surrounding area includes natural vegetation and a pathway made from red bricks, providing a welcoming access point.
Cottage in Standish

The Loon's Nest Cottage

4.96 out of 5 average rating, 106 reviews
Top guest favourite
A serene lakeside view showcases a wooden dock extending into calm waters, framed by lush greenery. Several Adirondack chairs are arranged in a semi-circle on the grass, offering a comfortable space for relaxation and enjoying the natural surroundings.
Cottage in Boothbay Harbor

Adorable Year Round Cottage - Walk to Town!

4.95 out of 5 average rating, 111 reviews
Guest favourite
A cottage situated by Sand Pond is observed, featuring a front porch that extends from the main structure. A private dock is visible with two kayaks secured, while lush greenery provides a backdrop of trees surrounding the property under clear blue skies.
Cottage in Litchfield

Cozy Lakefront 3 Bedroom 2 bath home on Sand Pond

4.92 out of 5 average rating, 104 reviews
Guest favourite
Cottage in Lincolnville

Call of the Loon - Water Edge Lake House

4.83 out of 5 average rating, 115 reviews
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

Cottage in the woods on Ocean Point

5.0 out of 5 average rating, 136 reviews
Top guest favourite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton

Eclectic Lakefront Cottage on Great East Lake

4.99 out of 5 average rating, 184 reviews
Top guest favourite
A circular tree swing hangs from a sturdy branch, overlooking a spacious green yard. The view includes a serene body of water with a dock and distant islands framed by trees under a clear blue sky.
Cottage in Friendship

Our charming,oceanfront, Bradford point cottage

4.92 out of 5 average rating, 335 reviews

Cabin rentals with a kayak

Top guest favourite
The cabin is viewed from the water, framed by lush greenery and tall trees. A spacious porch extends across the front, highlighting the cabin's inviting structure, while the calm water reflects the surrounding nature and the bright exterior of the building.
Cabin in Augusta

Price's Point - Cabin on the water

5.0 out of 5 average rating, 128 reviews
Top guest favourite
A serene lakeside view reveals a wooden dock with a reclining chair near the water's edge. Vibrant autumn leaves frame the scene, contrasting with the clear blue sky and calm lake. Rocky terrain adds natural texture to the tranquil environment, inviting relaxation.
Cabin in Raymond

Rustic, cozy cabin on Sebago Lake. A hidden gem.

4.93 out of 5 average rating, 182 reviews
Top guest favourite
A log cabin surrounded by trees is situated near the shoreline of the Ossipee River. A wooden deck extends from the cabin, and a red tandem kayak is positioned on a small dock, creating an inviting space for outdoor activities.
Cabin in Parsonsfield

Riverfront cabin between Portland & White Mtns.

4.96 out of 5 average rating, 285 reviews
Top guest favourite
Two wooden Adirondack chairs are positioned by the riverbank, offering a view of the calm water and lush greenery across the river. A small table sits between the chairs, surrounded by a sandy area dotted with leaves.
Cabin in Dresden

McKeen's Riverside Retreat

4.95 out of 5 average rating, 221 reviews
Superhost
A hot tub bubbles gently, surrounded by towering trees and a serene view of Moose Pond. The water reflects the clear blue sky and is framed by a tranquil landscape, creating a peaceful atmosphere for relaxation.
Cabin in Bridgton

Waterfront,Hot tub,Private dock,Freshly renovated

4.82 out of 5 average rating, 190 reviews
Top guest favourite
A scenic view captures a grassy area leading to a dock over Hobb's Pond. Four red Adirondack chairs are arranged around a fire pit made of stones. A mountain rises in the background, framed by fluffy clouds in a blue sky.
Cabin in Hope

Hobb’s House - Year Round Log Cabin on the Water

4.97 out of 5 average rating, 138 reviews
Top guest favourite
The entrance of a green cabin is framed by snow-covered ground and trees, with a glimpse of a lake visible in the background. A grill is positioned near the steps, and ski equipment leans against the wall, hinting at winter activities.
Cabin in Raymond

Idyllic Lakeside Cabin Winter Getaway

4.96 out of 5 average rating, 220 reviews
Top guest favourite
A contemporary cabin built with western red cedar sits amidst a snowy landscape, surrounded by tall trees and large boulders. A spacious deck is visible in front, leading to an entrance with steps, while two chairs are positioned on the deck for tranquil outdoor seating.
Cabin in Appleton

Smitten - you will be - Hear Silence.

4.94 out of 5 average rating, 368 reviews

Destinations to explore