
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.

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.

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.

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.

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.

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.

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.

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

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.

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).

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

Beautiful chalet home - walkable to beaches

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Private lake access, cozy retreat, skiing, shops

Waterfront: Relax & Unwind

Peaceful 4 bedroom lakehouse retreat

Enjoy Fall Foliage at the Lake

“A Beary Happy Place” stunning home, views & more
Cottage rentals with a kayak

Family & Pet Friendly, Lakefront Home

Completely updated detached cottage/Paugus Bay!

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

Peaceful Ossipee Lake Cottage Private Beach/Dock

Fun 2 bed 2 bath on a private Pequawket Lake.

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay

Cozy Waterfront Cottage w/ Private Dock & Kayaks

Serene Lakefront Retreat in Southern Maine
Cabin rentals with a kayak

+ Cannon Mountain Collective | Forest Undertones +

Beautiful private cabin on Big Squam Lake

Amish built cabin on 280 acres near North Conway

Get away at Crystal Lake

Private cabin with lake access, hot tub & firepit!

Barrett’s Cabin-Lakes Region-Private Trails

Secluded Cabin: View, Hot Tub, 10 min Walk to Lake

Lakefront Maine Retreat~PVT Dock & Year-Round Fun
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
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- Rentals with a kayak United States
- Sebago Lake
- White Mountain National Forest
- Squam Lake
- Story Land
- Weirs Beach
- Willard Beach
- Sunday River Resort
- Loon Mountain Resort
- Mount Washington Cog Railway
- Scarborough Beach
- Santa's Village
- East End Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- Cranmore Mountain Resort
- Omni Mount Washington Resort
- King Pine Ski Area
- Hills Beach
- Gunstock Mountain Resort
- Ragged Mountain Resort
- Conway Scenic Railroad
- Pleasant Mountain Ski Area
- Waterville Valley Resort
- Diana's Baths





