
Vacation rentals with a kayak in Madison
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Madison

Total vacation rentals
Explore 20 vacation rentals in Madison

Nightly prices starting at
Madison vacation rentals start at ﺩ.ﺇ 477 per night before taxes and fees

Verified guest reviews
Over 1,670 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Madison vacation 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 kayak rentals in Madison
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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.
LocationOutdoor spacesLayout

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.
ValueLocationIndoor spaces

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.
Outdoor spacesValueAccuracy

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.
Outdoor spacesValueQuiet

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!
LocationOutdoor spacesTV

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.
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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)
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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.
Outdoor spacesValueCheckout

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.
Outdoor spacesLocationCondition

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).
LocationValueNearby

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.
Outdoor spacesLocationWifi

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.
LocationOutdoor spacesAccess
Popular amenities for Madison kayak rentals
House rentals with a kayak

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

Birch Ledge Guesthouse--Four Season Maine Getaway
ValueOutdoor spacesWalkability

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

Hot Tub Haven: Dog-Friendly Retreat
LocationOutdoor spacesPets

Enjoy Fall Foliage at the Lake
LocationValueGetting around

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
LocationOutdoor spacesLong stay

Secluded Forest Getaway 2 Mins Downtown Littleton
LocationValueLayout

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski
LocationOutdoor spacesLaundry
Cottage rentals with a kayak

Charming Mountain view w/ River HSI Wi-Fi / Pets
Outdoor spacesLocationKitchen

The Loon's Nest Cottage
Outdoor spacesLocationLayout

Eclectic Lakefront Cottage on Great East Lake
ValueOutdoor spacesTV

Cozy Waterfront Cottage w/ Private Dock & Kayaks
LocationOutdoor spacesCondition

Recently renovated waterfront! Cedar Side Cottage
LocationOutdoor spacesGrill

Completely updated detached cottage/Paugus Bay!
LocationValueView

Serene Lakefront Retreat in Southern Maine
ValueLocationSleep quality

Peaceful Ossipee Lake Cottage Private Beach/Dock
Outdoor spacesLocationComfort
Cabin rentals with a kayak

Barrett’s Cabin-Lakes Region-Private Trails
ValueLocationHiking

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

Waterfront,Hot tub,Private dock,Freshly renovated
ValueOutdoor spacesCleanliness

Lakefront Maine Retreat~PVT Dock & Year-Round Fun
LocationOutdoor spacesKitchen

Private cabin with lake access, hot tub & firepit!
LocationOutdoor spacesGetting around

Get away at Crystal Lake
Outdoor spacesValueCheckout

+ Cannon Mountain Collective | Forest Undertones +
ValueLocationParks

Beautiful private cabin on Big Squam Lake
LocationValueAmenities
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,010 | ﺩ.ﺇ 1,036 | ﺩ.ﺇ 914 | ﺩ.ﺇ 856 | ﺩ.ﺇ 951 | ﺩ.ﺇ 962 | ﺩ.ﺇ 1,131 | ﺩ.ﺇ 1,142 | ﺩ.ﺇ 1,032 | ﺩ.ﺇ 1,050 | ﺩ.ﺇ 918 | ﺩ.ﺇ 1,142 |
| 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 |
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- 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
- Willard Beach
- Mount Washington Cog Railway
- Scarborough Beach
- East End Beach
- Santa's Village
- Tenney Mountain Resort
- Cranmore Mountain Resort
- Franconia Notch State Park
- Hills Beach
- Sunday River Resort
- Gunstock Mountain Resort
- Conway Scenic Railroad
- Ragged Mountain Resort
- Pleasant Mountain Ski Area
- Waterville Valley Resort
- Echo Lake State Park
- Diana's Baths
- Crawford Notch State Park
- Attitash Mountain Resort





