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Vacation rentals with a kayak in Madison

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Madison

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

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Treehouse in Sanford

4.9 out of 5 average rating, 480 reviews

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.

Cabin in Barnstead

4.95 out of 5 average rating, 199 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

This romantic & family friendly lakefront chalet comes with a private beach, hot tub, camp fire, and stunning views. It’s a serene home base to explore everything the Lakes Region has to offer. Mid Apr-Oct we also provide kayaks and paddle board. Enjoy the beach, swim, kayak, bike, fish, hike, or explore quintessential New England towns and food scene. Or simply dine with a view and play board games. We have poured our hearts into making this place romantic yet practical for families. Enjoy!

Cottage in Freedom

4.79 out of 5 average rating, 455 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Lakefront House, contemporary, amazing views, large deck, private lake beach & dock, steps from house (swimming). Very fast internet, multiple users. Private free parking. Fully equipped kitchen, AC, Smart TV & Modern shower room. Laundry Equipment, all Linen supplied. Sun trap West Facing Deck with loungers for relaxation. Canoe, life preservers & paddles included. 2 Fire pits & Grill. Boat put-in locally. Following cleaning codes: Airbnb & other authorities. Please ask any questions.

Home in Oxford

5 out of 5 average rating, 196 reviews

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Cabin in Conway

4.96 out of 5 average rating, 126 reviews

The Conscious Cabin

Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bath, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

Cottage in Parsonsfield

4.88 out of 5 average rating, 139 reviews

Riverpine Retreat - clean&bright waterfront home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Cabin in Oxford

4.94 out of 5 average rating, 125 reviews

Thompson Lake, Maine. discount winter rate Cottage

A refurbish 1967 knotty pine Cottage a short walk to lake and has lake rights. Located 400 feet from lake access. For swimming, FREE docking for your boat to fish, water ski or just cruise in Thompson lake. 14 miles one of Maines cleanest lakes. 6 Bicycles, 2- kayaks, 2-16 ft canoes, a 14 ft rowboat, and a paddle boat, fishing gear, firewood available for guest at no charge for fire pit. Propane and charcoal barbeques available at cottage. THERE IS NO WIFI.

Home in Hollis

4.99 out of 5 average rating, 401 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Cottage in Middleton

4.96 out of 5 average rating, 164 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Cottage in Dalton

4.96 out of 5 average rating, 168 reviews

Sunny Cottage on Private Lake

Relax and enjoy this bright, wood lined cottage overlooking a peaceful spring fed private lake with all you need for a spectacular getaway-Japanese soaking tub, Heat/AC, + super fast wifi. Cook in the well supplied kitchen or grill in the beach side pavilion. Walk the trails around the lake or to the adjacent 300 acre forest. DOG FRIENDLY with 68 acres of forest and trails, kayaks and water toys - the lake shared by only 2 other cottages

Guest suite in Conway

5 out of 5 average rating, 296 reviews

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Cottage in Conway

4.95 out of 5 average rating, 318 reviews

20ft from the Water with Mountain View!

This cozy cottage sits 20 ft from Pequawket Pond. We are the only cottage in this association that has 2 floors and directly on the pond. It has a spiral staircase that leads downstairs to the bedroom downstairs with walk out access. We are located within minutes to the Mount Washington Valley and all the amenities the valley has to offer. Ski resorts galore! We also have a kayak and 2 paddle boards available for our guests to use!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Popular amenities for Madison kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Limerick

4.93 out of 5 average rating, 115 reviews

Lakefront Getaway

Home in Greenwood

4.98 out of 5 average rating, 105 reviews

Maine lake front getaway!

Home in Windham

4.93 out of 5 average rating, 115 reviews

Waterfront Gem walkable to Restaurants!

Home in Wolfeboro

4.99 out of 5 average rating, 127 reviews

Tranquil Pondside Retreat

Home in Greenwood

4.96 out of 5 average rating, 132 reviews

Bright, Vintage Maine Home, Awaiting Adventure!

Home in Naples

4.98 out of 5 average rating, 156 reviews

Kayak to the Causeway-50s cottage with modern vibe

Home in Madison

4.96 out of 5 average rating, 67 reviews

Waterfront property with hot tub near North Conway

Home in Laconia

4.93 out of 5 average rating, 231 reviews

The Riverhouse Kayaks Pool Table Firepit Downtown

Cottage rentals with a kayak

Cottage in Alton

4.98 out of 5 average rating, 115 reviews

“Stay Awhile in the Lake's Region”

Cottage in Conway

4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

Cottage in Middleton

4.99 out of 5 average rating, 101 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

Cottage in Thornton

4.94 out of 5 average rating, 145 reviews

Cottage with antique charm view & river HSI Wi-Fi

Cottage in Ossipee

5 out of 5 average rating, 33 reviews

Peaceful Ossipee Lake Cottage Private Beach/Dock

Cottage in Kennebunkport

4.98 out of 5 average rating, 107 reviews

Charming Designer Cottage on Marsh

Cottage in Standish

4.92 out of 5 average rating, 116 reviews

Peaceful Lakeside Maine Retreat

Cottage in Buxton

4.98 out of 5 average rating, 142 reviews

Peaceful Cottage Retreat on Maine Flower Farm

Cabin rentals with a kayak

Cabin in Woodstock

4.96 out of 5 average rating, 139 reviews

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

Cabin in Grafton

4.87 out of 5 average rating, 216 reviews

Beautiful Serene Lake/Ski House with central AC

Cabin in Raymond

4.97 out of 5 average rating, 179 reviews

Idyllic Lakeside Cabin

Cabin in Holderness

4.86 out of 5 average rating, 102 reviews

Beautiful private cabin on Big Squam Lake

Cabin in Waterford

4.94 out of 5 average rating, 158 reviews

Lakeside Cabin Nestled in the Pines

Cabin in Harrison

4.99 out of 5 average rating, 121 reviews

Get away at Crystal Lake

Cabin in Bridgton

4.93 out of 5 average rating, 111 reviews

Private cabin w hot tub,skiing,firepit & mountains

Cabin in Greenwood

4.95 out of 5 average rating, 249 reviews

Camp Wigwam on North Pond - Swim,Paddle,Kayak,Fish

Quick stats about vacation rentals with a kayak in Madison

Total rentals
30 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore