
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 €113 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!
4.82 out of 5 average rating, 195 reviews
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.
4.82 out of 5 average rating, 191 reviews
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.
4.96 out of 5 average rating, 201 reviews
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!
4.91 out of 5 average rating, 161 reviews
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
4.82 out of 5 average rating, 127 reviews
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)
4.9 out of 5 average rating, 106 reviews
The Chalet~ 4 bed Lakefront Family Vacation
Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.
4.96 out of 5 average rating, 124 reviews
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!
4.98 out of 5 average rating, 210 reviews
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.
4.79 out of 5 average rating, 152 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.
4.99 out of 5 average rating, 412 reviews
Chalet/close to N Conway, far enough away from all
Please read our Coronavirus cleaning update. Quaint and cozy chalet located about 5 minutes from Conway and the hub of the White Mountains. As you pull into our neighborhood you notice several chalets on a paved road, winding up and over hills. Pull into our large carport to find our two level chalet that you have rented. The sounds of the babbling brook greet you as you exit your car with the inviting seating on both decks.
4.92 out of 5 average rating, 263 reviews
Waterfront Escape
Set just 20 feet from Pequawket Pond, this unique two-level cottage offers direct waterfront access in a quiet association. A spiral staircase leads to a lower-level bedroom with walk-out access, creating a distinct and private layout. Minutes from Mount Washington Valley, with easy access to skiing, hiking, and local shops. Guests also enjoy use of a kayak and two paddleboards for time on the water.
4.95 out of 5 average rating, 432 reviewsPopular amenities for kayak rentals in Madison
House rentals with a kayak

Hebron Historic Farmhouse
4.98 out of 5 average rating, 301 reviews
Enjoy Fall Foliage at the Lake
4.97 out of 5 average rating, 112 reviews
20 Mile Bay - Tuftonboro - Lake View Pet friendly
4.94 out of 5 average rating, 124 reviews
Waterfront, Wood stove & Private beach, Solo Stove
5.0 out of 5 average rating, 142 reviews
Fish Tales Cabin
4.96 out of 5 average rating, 148 reviews
Mountain home - Views +Woodstove + Firepit
4.99 out of 5 average rating, 149 reviews
Hale Pau Hana
4.99 out of 5 average rating, 99 reviews
Beautiful chalet home - walkable to beaches
4.92 out of 5 average rating, 63 reviewsCottage rentals with a kayak

RiverPine Retreat - Clean & Bright Waterfront Home
4.84 out of 5 average rating, 195 reviews
Eclectic Lakefront Cottage on Great East Lake
4.99 out of 5 average rating, 186 reviews
Charming Mountain View River Cottage w/ Pvt. Trail
4.96 out of 5 average rating, 193 reviews
Gorgeous Romantic Lakefront Getaway
4.99 out of 5 average rating, 120 reviews
Recently renovated waterfront! Cedar Side Cottage
4.99 out of 5 average rating, 114 reviews
Cozy Waterfront Cottage w/ Private Dock & Kayaks
4.83 out of 5 average rating, 121 reviews
The Loon's Nest Cottage
4.96 out of 5 average rating, 107 reviews
Completely updated detached cottage/Paugus Bay!
4.94 out of 5 average rating, 125 reviewsCabin rentals with a kayak

Mountain Lodge with Private Sauna
4.99 out of 5 average rating, 337 reviews
Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!
4.96 out of 5 average rating, 188 reviews
Barrett’s Cabin-Lakes Region-Private Trails
4.96 out of 5 average rating, 231 reviews
Breezy Moose - A Frame Cabin/ Pet friendly
4.94 out of 5 average rating, 157 reviews
Lakefront Maine Retreat~PVT Dock & Year-Round Fun
4.95 out of 5 average rating, 159 reviews
Hill Studio
4.98 out of 5 average rating, 116 reviews
Private cabin with lake access, hot tub & firepit!
4.91 out of 5 average rating, 163 reviews
+ Cannon Mountain Collective | Forest Undertones +
4.9 out of 5 average rating, 104 reviewsWhen is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €240 | €246 | €217 | €203 | €226 | €228 | €268 | €271 | €245 | €249 | €218 | €271 |
| 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
- Cranmore Mountain Resort
- Hills Beach
- East End Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- Pleasant Mountain Ski Area
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- Conway Scenic Railroad
- Ragged Mountain Resort
- Attitash Mountain Resort
- Echo Lake State Park
- Crawford Notch State Park





