
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.

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.
LocationOutdoor spacesCondition

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 spacesLocationHiking

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.
ValueOutdoor spacesView

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!
LocationValueIndoor spaces

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.
Outdoor spacesLocationAmenities

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)
Outdoor spacesValueFamily

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
ValueOutdoor spacesGrill

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.
ValueOutdoor spacesFamily

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.
ValueOutdoor spacesFamily

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).
Outdoor spacesValueWifi

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.
LocationValueTV

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.
Outdoor spacesLocationQuiet
Popular amenities for Madison kayak rentals
House rentals with a kayak

Birch Ledge Guesthouse--Four Season Maine Getaway
ValueOutdoor spacesWifi

Fish Tales Cabin
LocationOutdoor spacesHiking

Hot Tub Haven: Dog-Friendly Retreat
ValueLocationSkiing

Elevated 4-Season home - Mtn Views +A/C + Firepit
Outdoor spacesValueGetting around

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

Enjoy Fall Foliage at the Lake
LocationValueGrill

Secluded Forest Getaway 2 Mins Downtown Littleton
LocationValueTV

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski
Outdoor spacesValueGrill
Cottage rentals with a kayak

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

The Loon's Nest Cottage
Outdoor spacesLocationWifi

Eclectic Lakefront Cottage on Great East Lake
ValueOutdoor spacesPets

Cozy Waterfront Cottage w/ Private Dock & Kayaks
Outdoor spacesValueCleanliness

Recently renovated waterfront! Cedar Side Cottage
LocationOutdoor spacesGetting around

Completely updated detached cottage/Paugus Bay!
ValueLocationHiking

Serene Lakefront Retreat in Southern Maine
Outdoor spacesLocationHiking

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

Hill Studio
ValueOutdoor spacesKitchen

Barrett’s Cabin-Lakes Region-Private Trails
Outdoor spacesValueSleep quality

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

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

Lakefront Maine Retreat~PVT Dock & Year-Round Fun
ValueOutdoor spacesBathroom

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

Get away at Crystal Lake
Outdoor spacesValueHeating

+ Cannon Mountain Collective | Forest Undertones +
ValueOutdoor spacesLayout
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





