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

Adorable cedar cabin hideaway
Our cozy, warm cabin is set in a tranquil, picture perfect pine grove. A three minute walk to Davis Pond and 15 minutes from North Conway and ski resorts. The perfect getaway spot whether you need to unplug or plan an adventure. The home is comfortable and modern without compromising the rustic White Mountain charm, outfitted with all the amenities, a work station and a full outdoor space. We have put a lot of thought into this space and are confident that it will translate into a magical stay.

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.

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.

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!

Luxurious Mountainside Cabin! Fantastic Views!
Cozy Cabin with Sweeping Mountain Views! A great escape with total privacy. Relax by the Fire Pit overlooking the Mountains! Head up to North Conway to the White Mountains or go South to the Lakes Region. Then escape the traffic and retreat to the quiet of your Mountainside Cabin. Wood Fired Sauna on the premises! We provide everything you will need for your stay, and I mean everything, just bring a sense of adventure! Pets Welcome! *Pet Fee Applies! *Additional Fee for Sauna

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!

Beautiful Getaway Chalet - Mountain Views!
Private mountaintop home! My home is located in the beautiful community of Eidelweiss with private beaches, swimming, and a playground. Located minutes from North Conway and close to all Mount Washington Valley ski areas, activities, and tax-free shopping. Just a two-hour drive from Boston and you're ready to experience crystal clear rivers, pristine lakes, covered bridges, majestic mountains, picturesque hiking, and numerous local attractions and parks.

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.

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

Hot Tub•Yard•King Bed•15mins to North Conway

North Conway area waterfront 3-bedroom retreat

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

Romantic New England Historic Schoolhouse c1866

OakRidge Retreat - Hot Tub & Mountain Views

Modern Chalet: Pet-Friendly 3BD/2Bath | Kids Bunk

Stunning Design|HTub|Game Rm|Camping Theme Bedrm

2 bedroom lake view cabin with private dock and AC
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $294 SGD | $314 SGD | $260 SGD | $255 SGD | $274 SGD | $297 SGD | $334 SGD | $327 SGD | $286 SGD | $315 SGD | $272 SGD | $310 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 |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Madison?
Yes! Work meets play with ease at over 80 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.
How much does it cost to stay in house rentals in Madison?
Experience the best of Madison with our house 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 house rentals in Madison have wifi?
Absolutely! We offer over 100 house rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.
Do chalet rentals in Madison have a bbq area?
Absolutely! We offer over 10 chalet rentals with a bbq area in Madison. Enjoy a tailored experience with all the comforts you desire.
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.
What are the most popular amenities for Cabin Rentals in Madison?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 30 homes with a bbq area, over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Madison

Total holiday rentals
Explore 180 holiday rentals in Madison

Nightly prices starting at
Madison holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 7,890 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
90 properties have a dedicated workspace

Wifi availability
170 of Madison holiday 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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- Sebago Lake
- Squam Lake
- Story Land
- Scarborough Beach
- Sunday River Resort
- Weirs Beach
- Loon Mountain Resort
- Mount Washington Cog Railway
- Franconia Notch State Park
- Diana's Baths
- East End Beach
- Omni Mount Washington Resort
- Dunegrass Golf Club
- Funtown Splashtown USA
- Tenney Mountain Resort
- Willard Beach
- Cannon Mountain Ski Resort
- King Pine Ski Area
- Parsons Beach
- White Lake State Park
- Cliff House Beach
- Ferry Beach
- Laudholm Beach
- Waterville Valley Resort