
Holiday rentals with outdoor seating in Madison
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Madison
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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.

Waterfront w/ Private Beach, Fire Pit & Canoe
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 | 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.

Spacious home near mountains and lakes
Enjoy this spacious home that includes 3 bedrooms, a great kitchen ( upgraded cookware), and a huge game room downstairs with a pool table, new ping pong table, and foose ball table. Within minutes, you can be on Silver Lake, North Conway, Storylalnd, Kangamangus or make a visit to the White Mountians . Shop at the Settlers green outlets. Enjoy the comfort of the newly installed central air! Located in a nice quiet neighborhood. Come and go skiing at King Pine or many others in the area.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

1BR cozy, luxurious getaway @ Krista's Guesthouse
Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Cedar Hideaway: Walk to Pond, 15m N. Conway
Sip coffee on the screened porch listening to the wind in the pine grove. This modern cedar cabin is your sanctuary from the summer crowds, yet only 15 mins to the bustle of North Conway. Walk to the pond for a dip or read a book in the hammock. Equipped with fast WiFi and a fully stocked kitchen and charcoal grill. Cathedral Ledge and many hikes a short drive away. A tranquil, shady escape for those looking to slow down and breathe or your launchpad for White Mountain adventures.

White Mt Retreat w/ Beach Pass, New Kitchen, W/D
Get away from it all in our lovely, spacious home with its new kitchen, in Eaton, only 15 min to the shops and restaurants in North Conway and five minutes to King Pine Ski Area. Our property comes with a lake access pass to Crystal Lake public beach. Our place is ideal for outdoor enthusiasts, couples, chefs, and families. Our two floor home, with over 1600 sq. ft of living space, has two living room spaces providing private spaces for children and adults. We are owner-operated.

The Getaway Chalet: Relaxation, Views & Fire Pit
Experience the ultimate mountain escape at The Getaway Chalet in Madison, NH. This spacious 4-bedroom retreat in the Eidelweiss community features breathtaking views, two living areas, and 1-Gig Fiber internet. Enjoy private beach access to three ponds or relax on the expansive deck. The highlight? Evenings spent at the private fire pit under the stars. Minutes from North Conway shopping and White Mountain ski resorts, it’s the perfect basecamp for your next 5-star adventure..

Kirkland Cottage (A ski and lake escape)
Welcome to Kirkland Cottage! Located a two minute drive from Ossipee Lake and near the White Mountains, we are a great base for all New Hampshire has to offer! Explore lakes, mountains, and hiking trails, while being just an hour from Portland and Portsmouth. Kirkland Cottage house is 9 minutes to King Pine Ski area, 30 minutes to Cranmore, and 25 minutes to North Conway, which has great shopping, skiing, hiking, and lots of restaurants.

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, multiple skiing resorts
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 outdoor seating rentals in Madison
House rentals with outdoor seating

The Niche...crafted & forged

Modern 4-Season Escape w/ Mtn Views, A/C & Firepit

Hygge Up North | Rustic White Mountain Home Base

Luxe Lodge in the Woods! With Sauna & Hot tub

Big Blue Chalet - A Mountain View Getaway

Mountain view 3 bedroom.

Our Mountain Retreat – Lake Ossipee Access

Spacious 3 bedroom Mountain Chalet -Conway, NH
Apartment rentals with outdoor seating

Waterfront on Opechee

Humble abode in the heart of the White Mountains

Charming Carriage House in the White Mountains

Lovely Apartment in Thornton

The Misty Mountain Hideout

Studio, pet friendly, river views, Jackson NH

Stone Mountain Guest House 2nd Floor Apt.

4.93 Star Studio | Loon Mtn | River & Mtn Views
Apartment rentals with outdoor seating

Cozy condo with North Conway at your finger tips!

Spacious Condo-Attitash Ski-Storyland-Saco & More!

Loon Mountain Area Rental - 2Br/2Ba

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104

Cozy, clean, 2nd floor condo in Conway, NH!

Cozy Family Retreat with Saco River Access

NEW! Mtn Views • Fireplace • Hot Tub • Pool Escape

Downtown Wolfeboro condo on Winnipesaukee w/Dock!
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $332 SGD | $354 SGD | $308 SGD | $254 SGD | $287 SGD | $292 SGD | $337 SGD | $321 SGD | $279 SGD | $313 SGD | $297 SGD | $334 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 outdoor seating in Madison

Total holiday rentals
Explore 110 holiday rentals in Madison

Nightly prices starting at
Madison holiday rentals start at $76 SGD per night before taxes and fees

Verified guest reviews
Over 6,490 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
110 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 a hot tub Madison
- Rentals with beach access Madison
- Family-friendly rentals Madison
- House rentals Madison
- Rentals with a patio Madison
- Rentals with lake access Madison
- Rentals with a washing machine and dryer Madison
- Waterfront rentals Madison
- Rentals with a firepit Madison
- Rentals with a kayak Madison
- Cabin rentals Madison
- Chalet rentals Madison
- Pet-friendly rentals Madison
- Rentals with a fireplace Madison
- Rentals with outdoor seating Carroll County
- Rentals with outdoor seating New Hampshire
- Rentals with outdoor seating United States
- White Mountain National Forest
- Sebago Lake
- Squam Lake
- Story Land
- Sunday River Resort
- Weirs Beach
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Willard Beach
- East End Beach
- Tenney Mountain Resort
- Franconia Notch State Park
- King Pine Ski Area
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- Cranmore Mountain Resort
- Cannon Mountain Ski Resort
- Waterville Valley Resort
- Ragged Mountain Resort
- Diana's Baths
- Funtown Splashtown USA
- Conway Scenic Railroad
- Pleasant Mountain Ski Area





