
Holiday rentals with a kayak in Madison
Find and book unique kayak rentals on Airbnb
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!

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.

White Mtns Waterfront Chalet w/ Private Beach
This charming chalet is nestled on the edge of Little Pea Porridge Pond in the enchanting village of Eidelweiss, an alpine oasis just a short drive from Mt Washington Valley. Enjoy campfires on a private sandy beach; Fishing, swimming and boating in the warmer months; Snowmobiling, skiing and ice-skating in the Winter season. Nearby attractions incl. King Pine, Cranmore and Attitash Ski Resorts; N Conway Village; Kancamaugus Highway, Hiking Trials, Waterfalls, shopping and gourmet restaurants.

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 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!

Clean, quaint studio apartment on small farm
Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

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

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)

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

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.

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.

Tiny Lakefront Cottage
Escape to our beautifully redesigned cottage on serene Pequawket Pond, nestled in the heart of New Hampshire's White Mountains. This studio, one of just seven in a private association, offers maximized comfort and space just steps from the water. Enjoy complimentary use of our kayak and two paddleboards, or simply unwind on the patio with grill, soaking in the breathtaking pond views. Your perfect lakeside retreat awaits!.
Popular amenities for kayak rentals in Madison
House rentals with a kayak

Lakefront Oasis Priv Beach Swim Kayak Fish FirePit

Fish Tales Cabin

Lakefront Boutique Cabin

Tranquil Pondside Retreat

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

Lovely 2 Bedroom Loft at Loon Mountain! Lincoln NH

Sokokis Lake House

Spacious Belleau Lake House Amongst the Trees
Cottage rentals with a kayak

“Stay Awhile in the Lake's Region”

Gorgeous Romantic Lakefront Getaway

Cozy Lakeside Retreat: Pet-Friendly & Year-Round

Completely updated detached cottage/Paugus Bay!

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

Quaint New England Cottage in the Pines | Lakeside

Peaceful Ossipee Lake Cottage Private Beach/Dock

RK North : All season Waterfront cottage with dock
Cabin rentals with a kayak

Cozy Cabin w/ Pond Access

+ Cannon Mountain Collective | Forest Undertones +

Beautiful private cabin on Big Squam Lake

Lakeside Cabin Nestled in the Pines

Get away at Crystal Lake

Private cabin w hot tub,skiing,firepit & mountains

Barrett’s Cabin

Lake Front with Private Dock - BRAND NEW Furniture
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $353 SGD | $366 SGD | $357 SGD | $278 SGD | $376 SGD | $359 SGD | $402 SGD | $406 SGD | $366 SGD | $338 SGD | $313 SGD | $387 SGD |
| 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 |
Quick stats about holiday rentals with a kayak in Madison

Total holiday rentals
Explore 30 holiday rentals in Madison

Nightly prices starting at
Madison holiday rentals start at $170 SGD per night before taxes and fees

Verified guest reviews
Over 1,540 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!
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- Rentals with beach access Madison
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- Rentals with a patio Madison
- Rentals with a firepit Madison
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- Rentals with a hot tub Madison
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- Rentals with a kayak Carroll County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Sebago Lake
- Squam Lake
- Story Land
- Scarborough Beach
- Sunday River Resort
- Weirs Beach
- Loon Mountain Resort
- Mount Washington Cog Railway
- Franconia Notch State Park
- Diana's Baths
- East End Beach
- Omni Mount Washington Resort
- Dunegrass Golf Club
- Funtown Splashtown USA
- Tenney Mountain Resort
- Willard Beach
- Cannon Mountain Ski Resort
- King Pine Ski Area
- Parsons Beach
- White Lake State Park
- Ferry Beach
- Cliff House Beach
- Laudholm Beach
- Waterville Valley Resort




