
Vacation rentals in Madison
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Top-rated vacation rentals in Madison
Guests agree: these stays are highly rated for location, cleanliness, and more.

Lost Compass Cabin•Relax•Reset Explore
Escape to the White Mountains in this cozy, private Conway cabin-just minutes from North Conway shops, Cranmore, and the Kancamagus Highway. Perfect for families, couples, and small groups looking for a quiet retreat with easy access to skiing, hiking, and downtown fun. Seasonal Highlights ❄️ Winter ❄️ •Ski Cranmore•Attitash•Loon •Cross country skiing•Ice skating •Cozy nights by the fireplace ☀️Spring/Summer☀️ •Hike off the Kanc •Diana’s Baths •Kayaking•Swimming holes 🍁Fall🍁 •Leaf peeping

Perfect Family Getaway On Lake Ossipee
Our 10 year old home has four bedrooms three baths, theater room, gas fireplace, bar outdoor fire pit, open concept kitchen, nestled in a mountain landscape. Beautiful private beach with a playground, picnic area and boat launch only a short walk away. Tennis courts and a basketball court centrally located within the community. Boat rentals available on the lake. Multiple ski areas close by. Easy access to local and state snowmobile trails and the lake for ice fishing right out of the driveway.

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.

Mountain View Studio
This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

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.

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.

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..

The Village House
Welcome to our recently renovated home , built in the late 1890's in the heart of beautiful Tamworth Village, right on quiet Main st. A quick 5 minute walk to "downtown", Remick Farm and museum, Barnstormers summer theatre and The Other Bakery. Tamworth is home to many local hiking trails from easy walks to over 4000 foot summits. Great place in the winter with miles of free , groomed cross-country skiing and snowshoeing trails as well.

Little Bear Lodge | Cozy Log Cabin in the Pines
Escape to the Little Bear Lodge located in the heart of the White Mountains! Brimming with charm and character, this quintessential log cabin provides plenty of space for the whole family in a private, idyllic mountain setting. Bring your bags & leave everything else to us. Fully stocked kitchen & coffee bar, cozy living room, and spacious bedrooms. Lots of outdoor space too - a screened in porch, deck, patio and beautiful landscaping.

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.
Popular amenities for Madison vacation rentals
Other great vacation rentals in Madison

Beautiful chalet home - walkable to beaches

Retreat for 8|Pvt Hot Tub|Pets|Stunning Mtn Vistas

Mountainside Chalet at Mittersill

Meadow + Stream Views | Clawfoot Tub | Near Conway

The SchoolHouse

New-Adorable Spacious "Garden Cape" Guest Suite

River Street Retreat

StoneWood Lodge | Lake Access | Arcade Room | Yard
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $313 CAD | $334 CAD | $277 CAD | $271 CAD | $292 CAD | $316 CAD | $356 CAD | $348 CAD | $304 CAD | $335 CAD | $317 CAD | $356 CAD |
| 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 |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Madison?
Four-legged friends are welcome in Madison. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Madison?
Yes! Work meets play with ease at over 90 vacation rentals in Madison featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly chalet rentals in Madison?
Madison has more than 10 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Madison?
Experience the best of Madison with our cabin rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do chalet rentals in Madison have air conditioning?
Absolutely! We offer over 10 chalet rentals with air conditioning in Madison. Enjoy a tailored experience with all the comforts you desire.
Do chalet rentals in Madison have wifi?
Absolutely! We offer over 10 chalet rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Madison have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Madison?
Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with air conditioning, over 100 homes with wifi, over 60 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Madison

Total vacation rentals
Explore 180 vacation rentals in Madison

Nightly prices starting at
Madison vacation rentals start at $83 CAD per night before taxes and fees

Verified guest reviews
Over 8,300 verified reviews to help you choose

Family-friendly vacation rentals
160 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
170 of Madison vacation rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Madison rentals

4.9 Average rating
Madison stays are highly rated by guests—averaging 4.9 out of 5!
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- White Mountain National Forest
- Sebago Lake
- Squam Lake
- Story Land
- Sunday River Resort
- Weirs Beach
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- Willard Beach
- Tenney Mountain Resort
- King Pine Ski Area
- Franconia Notch State Park
- East End Beach
- Gunstock Mountain Resort
- Omni Mount Washington Resort
- Cannon Mountain Ski Resort
- Ragged Mountain Resort
- Diana's Baths
- Waterville Valley Resort
- Funtown Splashtown USA
- Pleasant Mountain Ski Area
- Conway Scenic Railroad




