
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 $166 SGD 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.

Gorgeous Romantic Lakefront Getaway
Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.
ValueLocationBeach

Hill Studio
Take it easy at this unique and tranquil getaway. This former Architect’s studio has been set up as a one bedroom guest house. It is a wonderful spot to relax and snuggle up next to the fire with your favorite book, beverage, or a special someone. The studio is very private with only the trees or maybe a visiting moose to see in. We are 30 min. to Ragged Mountain and Newfound Lake. We have a friendly dog and preapproved well-behaved pets are welcome. An all-wheel drive car is needed in winter.
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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.
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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!
ValueLocationHiking

Secluded Forest Getaway 2 Mins Downtown Littleton
Welcome to your private White Mountains retreat - a spacious, family-friendly vacation home on 5 forested acres just 2 minutes from award-winning downtown Littleton, NH. Our peaceful 3-bedroom home sleeps 8 and offers the perfect balance of comfort, nature, and accessibility. Relax by the fire, grill on the deck, cook s'mores over the firepit, or load up the kayaks - whether you're after a relaxing family vacation, a forest office, or an adventure basecamp, Stone's Throw is the spot.
ValueLocationGrill

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.
ValueOutdoor spacesPets

Handcrafted A Frame near Newfound Lake and Hiking
Relax and recharge at Millmoon A-Frame Cabin 2 hours from Boston - Exhale under the stars by the fire pit - Grill on the back deck w/ forest views - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Explore hiking, biking & snowshoeing nearby at Wellington and Cardigan Mountain State Parks & AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.
ValueOutdoor spacesNearby

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.
LocationOutdoor spacesCleanliness

Breezy Moose - A Frame Cabin/ Pet friendly
Welcome to the White Mountain National Forest. Take it easy at this unique and tranquil getaway. Cozy A Frame Cabin with AC situated on quite side road. Perfect for romantic getaway or family trip. House is situated for family of 3 (2 adults plus 1 kid). Minutes walking from swimming whole on the Baker River. Ideally located, 30 minutes to Loon & Cannon for skiing, and convenient to I-93 or I-91. Newly renovated and furnished. Pet friendly (pet fee).
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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.
LocationValueComfort

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.
Outdoor spacesLocationWalkability

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.
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Popular amenities for kayak rentals in Madison
House rentals with a kayak

Beautiful chalet home - walkable to beaches
Outdoor spacesLocationBathroom

Fish Tales Cabin
LocationValueDecor

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski
LocationOutdoor spacesCheck-in

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

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Outdoor spacesValueCheckout

Private lake access, cozy retreat, skiing, shops
LocationOutdoor spacesAmenities

Waterfront: Relax & Unwind
Outdoor spacesLocationPets

Enjoy Fall Foliage at the Lake
ValueOutdoor spacesAmenities
Cottage rentals with a kayak

Completely updated detached cottage/Paugus Bay!
ValueLocationSleep quality

Charming Mountain view w/ River HSI Wi-Fi / Pets
ValueOutdoor spacesPets

Peaceful Ossipee Lake Cottage Private Beach/Dock
Outdoor spacesLocationGrill

The Cozy Cottage @ Loon Pond, Close to Event Venue
Outdoor spacesLocationAmenities

Fun 2 bed 2 bath on a private Pequawket Lake.
ValueLocationCheckout

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay
LocationValueView

Cozy Waterfront Cottage w/ Private Dock & Kayaks
ValueLocationAir conditioning

Serene Lakefront Retreat in Southern Maine
ValueLocationBeach
Cabin rentals with a kayak

+ Cannon Mountain Collective | Forest Undertones +
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Long Pond Cabin Retreat
Outdoor spacesLocationWalkability

Beautiful private cabin on Big Squam Lake
ValueLocationSleep quality

Amish built cabin on 280 acres near North Conway
Outdoor spacesLocationComfort

Get away at Crystal Lake
LocationValueLong stay

Private cabin with lake access, hot tub & firepit!
Outdoor spacesValueHiking

Barrett’s Cabin-Lakes Region-Private Trails
ValueLocationAccess

Lakefront Maine Retreat~PVT Dock & Year-Round Fun
ValueOutdoor spacesDecor
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $352 SGD | $361 SGD | $319 SGD | $298 SGD | $332 SGD | $335 SGD | $394 SGD | $398 SGD | $360 SGD | $366 SGD | $320 SGD | $398 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 |
Destinations to explore
- New York City Holiday rentals
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- Cabin rentals Madison
- Rentals with beach access Madison
- Family-friendly rentals Madison
- Rentals with lake access Madison
- Pet-friendly rentals Madison
- Chalet rentals Madison
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- 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
- Sunday River Resort
- Loon Mountain Resort
- Willard Beach
- Santa's Village
- Scarborough Beach
- Mount Washington Cog Railway
- East End Beach
- Cranmore Mountain Resort
- Tenney Mountain Resort
- Hills Beach
- Franconia Notch State Park
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- King Pine Ski Area
- Conway Scenic Railroad
- Ragged Mountain Resort
- Pleasant Mountain Ski Area
- Attitash Mountain Resort
- Waterville Valley Resort





