
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 $182 AUD per night before taxes and fees

Verified guest reviews
Over 1,570 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Madison holiday rentals include Wi-Fi 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 Accommodation with a Kayak in Madison
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Privacy, River, Pond, A frame Hot Tub EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

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.

Mountain Lodge with Private Sauna
Escape to Darkfrost Mountain Lodge, less than 2 hours from Boston - Gather under the stars by the fire pit & garden - Relax or grill on patio with woodland views - Enjoy a pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain - Explore hiking, biking & snowshoeing nearby at Wellington, Cardigan Mountain State Parks, AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 available cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

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.

Elevated 4-Season home - Mtn Views +A/C + Firepit
Wake up to mountain views, sip coffee on the wrap-around deck, and breathe in the fresh Maine air. At Mountain View Lodge, every detail is designed for you to relax and recharge. Spend your days skiing at Pleasant Mountain, hiking local trails, or floating down the Saco River - and your evenings gathered around the firepit or curled up by the woodstove. With three bedrooms, two baths, and a fully equipped kitchen, there's space for families, friends, and couples to enjoy all four seasons.

N Conway 10 min/Waterfront /Private Beach/fire pit
Peace comes dropping slow at this pond side chalet in Eidelweiss Village, an alpine oasis only 15 mins from North Conway. Here, on a private sandy beach, you can swim in calm waters; take a canoe or a kayak out for a leisurely row; toast marshmallows at a private fire pit and gaze up at a trillion stars in night skies unpolluted by urban glare. In the Winter months, you can ice skate on Little Pea Porridge Pond or go skiing at Pine King or Cranmore, or simply enjoy dinner with a view...

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!

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.

Sunny Waterfront Cottage at FarAway Pond
Spring Skiing! Sugar and Snow 20%discount! March is maple sugar and BIG snow season at Bretton Woods (only 20 min. away). This bright, wood lined cottage has all you need for a peaceful getaway-Hot Tub in private pavilion, Japanese soaking tub, (small) Heat/AC, +fast wifi. Cook in the kitchen or grill in the beach side pavilion. With 68 acres + miles of trails to a nearby state forest, this is the perfect base for peak-season skiing and serene winter adventure. Dogs welcomed!

Waterfront, Wood stove & Private beach, Solo Stove
Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

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.

Chalet/close to N. Conway, multiple skiing resorts
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.
Popular amenities for Madison kayak rentals
Holiday House Rentals with a Kayak

Fish Tales Cabin

Warm Lakefront Log Cabin · Hot Tub · Game Room

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Peaceful Lakefront Retreat

Hot Tub Haven: Dog-Friendly Retreat

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

LongLake-PrivateDockSandyBeach/PaddleBoards/SUPs
Cottages with a kayak

“Stay Awhile in the Lake's Region”

Gorgeous Romantic Lakefront Getaway

Completely updated detached cottage/Paugus Bay!

Cottage w/ charm, mountain view & river HSI Wi-Fi

Peaceful Ossipee Lake Cottage Private Beach/Dock

Cozy Waterfront Cottage w/ Private Dock & Kayaks

Peaceful Lakeside Maine Retreat

The Loon's Nest Cottage
Cabin rentals with a kayak

+ Cannon Mountain Collective | Forest Undertones +

Beautiful private cabin on Big Squam Lake

Lakefront Getaway Cabin/Private Sandy Beach!

Get away at Crystal Lake

Private cabin with lake access, hot tub & firepit!

Harolds Camp: Lake Winnipesaukee Waterfront w/dock

Cozy Lake Cabin Hike Kayak Fish XLFirePit White MT

Barrett’s Cabin-Lakes Region-Private Trails
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $386 AUD | $396 AUD | $349 AUD | $299 AUD | $404 AUD | $386 AUD | $432 AUD | $436 AUD | $394 AUD | $401 AUD | $351 AUD | $436 AUD |
| 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
- Plainview Holiday rentals
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- House rentals Madison
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- Rentals with a hot tub Madison
- Pet-friendly rentals Madison
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- Rentals with a fireplace Madison
- Rentals with a patio Madison
- Rentals with a washing machine and dryer Madison
- Waterfront rentals Madison
- Rentals with beach access Madison
- Family-friendly rentals Madison
- Rentals with a fire pit Madison
- Rentals with a kayak Carroll County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- White Mountain National Forest
- Sebago Lake
- Story Land
- Squam Lake
- Weirs Beach
- Sunday River Resort
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Willard Beach
- East End Beach
- Attitash Mountain Resort
- Owl's Nest Resort
- Omni Mount Washington Resort
- Tenney Mountain Resort
- Franconia Notch State Park
- King Pine Ski Area
- Cranmore Mountain Resort
- Gunstock Mountain Resort
- Waterville Valley Resort
- Cannon Mountain Ski Resort
- Conway Scenic Railroad
- Ragged Mountain Resort
- Funtown Splashtown USA





