
Holiday rentals with a kayak in Madison
Find and book unique kayak rentals on Airbnb
Quick stats about holiday rentals with a kayak in Madison

Total holiday rentals
Explore 20 holiday rentals in Madison

Nightly prices starting at
Madison holiday rentals start at €112 per night before taxes and fees

Verified guest reviews
Over 1,670 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
10 properties have a dedicated workspace

Wifi availability
20 of Madison holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Madison rentals

4.9 Average rating
Madison stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with kayak in Madison
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Hot Tub Haven: Dog-Friendly Retreat
Welcome to your perfect getaway! Our charming home offers the perfect balance of relaxation and entertainment, with a private hot tub and cozy fireplace for ultimate comfort. The large yard is perfect for furry friends, who are always welcome to join the fun. Inside, our games room offers endless entertainment for kids and adults alike. Whether you're looking for a romantic retreat or a fun-filled family vacation, our dog-friendly oasis is the perfect destination. Experience the ultimate escape!

Waterfront,Hot tub,Private dock,Freshly renovated
Welcome to the freshly renovated Cabin on a Moose Pond!Nestled near the hills of Pleasant Mountain.Enjoy a day at the lake fishing,swimming,skiing,hiking or snowmobiling. In the evening,relax in the new hot tub,watch a movie on the home theater or challenge friends to video games.End your day by the campfire making s’mores by the pond. Spend a lazy day on the hammock or take a day trip to explore regional attractions in beautiful ME and NH. For your safety, the area is under video surveillance.

Eclectic Lakefront Cottage on Great East Lake
Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

The Conscious Cabin | Getaways + Retreats
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 bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

Conway Waterfront Base for Your Family Memories!
Waterfront gem in the middle of it all! Designed to be the ideal getaway regardless of the season. Beautiful views out master bedroom, the back porch and from the backyard year round. The feel of seclusion while still being near all activities! Enjoy the water on one of the two kayaks or in the 2 canoes. Perfect base for skiing, hikes and sightseeing! Easy drive to North Conway, Kankamangus Highway, White Mountains, Story Land and so much more! No need to leave the property, just enjoy!

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski
Chocorua Lake front house to enjoy friends & family! Hottub, ski, hike, kayak,fish,swim,fire pit & relax! Fantastic Winter Holiday Ski Vacation or Summer Getaway, Shopping &more. Near Tamworth Wedding venues. Renovated 3 bedroom on crystal clear Chocorua Lake near North Conway, NH. Beautiful in every season enjoy the best of New England Fall Foliage, Summer Lake, Winter or just relax by the fireplace ! Kayaks/dock onsite. Outdoor Hottub. **limited time offer $150/nt to add xtra cabin

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.

White Mountain Mansion -Secluded property, pets OK
Tucked away on five acres of beautiful wooded mountain land, we have our beautiful 5 bedroom, 5 bathroom home. 10 min outside of North Conway! Not only do we have all common amenities, we have some pretty special ones too: a movie theatre room, a gym, surround sound in 3 rooms, an upstairs lounge area equipped with a Billiards, Ping Pong, and a poker table! Not to mention a beautiful wood burning fireplace, and extra sleeping options for guests (that aren’t factored into bedrooms)

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

Pond-Side Chalet • Private Beach • Canoe & Kayak
"So close to the water's edge you could practically fish from the deck." That's what guests say about Idylweiss Chalet, our pond-side chalet in Eidelweiss Village, 15 minutes from North Conway. Mornings on the deck with the loons calling across Little Pea Porridge Pond. Afternoons on the private sandy beach with the canoe and kayak. Sleeps seven across three bedrooms and two full bathrooms. A short drive to Storyland, ski resorts, and the Kancamagus Highway.

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.

Red Shed Cottage at Pickett Hill Farm
Red Shed Cottage is a renovated carriage house situated on the property of Pickett Hill Farm, an 1830's complex. The cottage is ideally situated to capture the essence of the rural countryside of the Lakes Region of Western Maine. Pickett Hill Farm offers splendid views of open fields, Pleasant Mountain and the surrounding forests, attracting naturalists, painters and photographers, as well as those who seek a restful vacation.
Popular amenities for kayak rentals in Madison
House rentals with a kayak

Elevated 4-Season home - Mtn Views +A/C + Firepit

Hebron Historic Farmhouse

Enjoy Fall Foliage at the Lake

Waterfront, Wood stove & Private beach, Solo Stove

20 Mile Bay - Tuftonboro - Lake View Pet friendly

“A Beary Happy Place” stunning home, views & more

Fish Tales Cabin

Beautiful chalet home - walkable to beaches
Cottage rentals with a kayak

Charming Mountain View River Cottage w/ Pvt. Trail

Recently renovated waterfront! Cedar Side Cottage

Gorgeous Romantic Lakefront Getaway

Cozy Waterfront Cottage w/ Private Dock & Kayaks

Completely updated detached cottage/Paugus Bay!

Peaceful Ossipee Lake Cottage Private Beach/Dock

Serene Lakefront Retreat in Southern Maine

Family & Pet Friendly, Lakefront Home
Cabin rentals with a kayak

Mountain Lodge with Private Sauna

Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!

Barrett’s Cabin-Lakes Region-Private Trails

Breezy Moose - A Frame Cabin/ Pet friendly

Lakefront Maine Retreat~PVT Dock & Year-Round Fun

Private cabin with lake access, hot tub & firepit!

Get away at Crystal Lake

+ Cannon Mountain Collective | Forest Undertones +
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €236 | €243 | €214 | €200 | €223 | €225 | €265 | €267 | €242 | €246 | €215 | €267 |
| Avg. temp | -15°C | -14°C | -11°C | -5°C | 2°C | 8°C | 10°C | 9°C | 6°C | 0°C | -6°C | -11°C |
Destinations to explore
- Cabin rentals Madison
- Rentals with beach access Madison
- Family-friendly rentals Madison
- Rentals with lake access Madison
- Pet-friendly rentals Madison
- Chalet rentals Madison
- Waterfront rentals Madison
- Rentals with a hot tub Madison
- House rentals Madison
- Rentals with a kayak Carroll County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Sebago Lake
- White Mountain National Forest
- Squam Lake
- Story Land
- Weirs Beach
- Loon Mountain Resort
- Willard Beach
- Scarborough Beach
- Mount Washington Cog Railway
- Santa's Village
- Sunday River Resort
- East End Beach
- Cranmore Mountain Resort
- Hills Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- Gunstock Mountain Resort
- Omni Mount Washington Resort
- Pleasant Mountain Ski Area
- Conway Scenic Railroad
- Ragged Mountain Resort
- Attitash Mountain Resort
- Diana's Baths
- Echo Lake State Park





