
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.

N. Conway…Cozy Cabin, Centrally Located
Our newly renovated cabin is family friendly (childproofed), stylish, and cozy with lovely wooden accents throughout! It is newly furnished and has brand new mattresses! This cabin is wonderfully located just off of Westside Rd. a mere skip away from Echo Lake, Cathedral Ledge, Diana's Baths etc...It is a 5 - 8 minute drive to North Conway Village and Cranmore Ski Resort; and a 5 - 8 minute drive from Settler's Green Outlets, grocery stores etc...with numerous other popular destinations nearby.

Cozy Condo at Attitash!
Enjoy activities & beautiful scenery offered at Attitash Mountain Village, in the White Mountains! This cozy one bedroom, 2nd floor condo sleeps four, and includes a completely renovated kitchen/living area and bathroom! You will be just steps away from a beautiful pool pavilion, tennis courts, playgrounds, the Saco River Beach, hot tubs, fire pits, an arcade, and a fitness center. Nestled among all the summer attractions of the area- 10 minutes to Story Land! Always something fun to do!

Cozy Guest Suite in White Mountain National Forest
Guest Suite, mother-in-law apartment with private entrance. One bedroom with living room, dining area, kitchen, stove, full refrigerator. WiFi and a futon couch that turns into a bed in the living room. The converted basement apartment is a comfortable, and cozy place to stay while visiting the Mount Washington Valley. Perfect for adventuring, climbers, hikers, bikers and skier/snowboarders. Have a hot pot of organic local coffee and get outside in the beautiful Mount Washington Valley!

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!

Cozy guest house near Littleton and Cannon Mtn
This rustic north country cabin offers 2 bedrooms and 1 bath for up to 4 guests. It has been renovated with comfortable beds and pillows, new appliances, a toasty pellet stove, a beautiful 75" TV with soundbar and subwoofer for movie nights, ample parking. It's located 9 minutes south of downtown Littleton and 11 minutes north of Cannon Mountain. Whether you're visiting for winter sports, leaf watching, mountaineering, or Polly's Pancakes, we're close to the action.

HAPPY TREES: swanky chalet near Conway Lake & Saco
Happy Trees is a vintage chalet that has been thoughtfully renovated and styled. Our place is bright, airy, and open. It's the perfect home base for whatever you may want to do whether it's skiing, swimming, hiking, or simply relaxing and lounging around. Our place is a short walk to Conway Lake and a short drive from the Saco River. Conveniently located minutes from North Conway village. Follow us on IG (@happytrees_cabin) for additional content & information.

Mountain Treehouse Guesthouse
Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

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.

Dog friendly, lower level apartment off the "Kanc"
The cabin is located off Kancamagus Hwy, one of the most scenic roads in the US. The outdoor activities are endless, from hiking, biking, snowshoeing, alpine/x country skiing , golfing, horseback riding and tons of shopping at the infamous "outlet stores" You’ll love the cabin because of it's rustic motif, quiet neighborhood, and fresh mountain air. The cabin is good for couples, solo adventurers, biz travelers, and furry friends .

Cozy & Charming Custom Log Home in Madison
Unwind in our cozy custom log home, newly crafted with all the amenities! Featuring a gorgeous stone chimney, open floor plan, covered porch, and large deck. Minutes from North Conway shopping, skiing, trails, rivers, and lakes. Located on 113 in Madison. In the winter, snowmobile or snowshoe from the cabin! Very clean, tidy, and stocked with necessities. Relax and enjoy all our beautiful area has to offer.

Riverfront cabin between Portland & White Mtns.
Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.

Modern A-frame w/ Mountain Views - North Conway
Welcome to our cozy 3-bedroom A-frame cabin, nestled in the heart of North Conway. Originally built by our grandparents in the 1960's, this A-frame serves as the perfect home-base for adventuring and exploring all that the White Mountains have to offer; skiing, snowshoeing, snowmobiling, hiking, biking, breweries, dining, floating the Saco, leaf-peeping and the like!
Popular amenities for Madison vacation rentals
Other great vacation rentals in Madison

Welcome to Lakota! A Cozy 2 BR Cottage.

Beautiful, updated cozy cottage

3 bdrm + game room - Lake, Ski, Hike, Shop!

Hot Tub|Fire Pit|Game Rm|Fire Pl|1Acre wooded lot

Saco River Frontage

Alpine Retreat

2 bedroom lake view cabin with private dock and AC

Waterfront Home w/ Dock, Screened Porch, Dogs Ok!
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $308 CAD | $328 CAD | $272 CAD | $267 CAD | $287 CAD | $311 CAD | $350 CAD | $342 CAD | $300 CAD | $330 CAD | $312 CAD | $350 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 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 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.
Do cabin rentals in Madison have wifi?
Absolutely! We offer over 20 cabin rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Madison?
Madison has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in chalet rentals in Madison?
Experience the best of Madison with our chalet rentals, starting at about $130 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 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 100 homes with wifi, over 60 homes with a bbq area, over 90 homes with air conditioning, 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 $82 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
- Loon Mountain Resort
- Scarborough Beach
- Weirs Beach
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- King Pine Ski Area
- Tenney Mountain Resort
- Franconia Notch State Park
- Willard Beach
- East End Beach
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- Cannon Mountain Ski Resort
- Diana's Baths
- Ragged Mountain Resort
- Waterville Valley Resort
- Funtown Splashtown USA
- Palace Playland
- Conway Scenic Railroad




