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Madison vacation rentals

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Top-rated vacation rentals in Madison

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Cabin in Conway

4.94 out of 5 average rating, 335 reviews

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.

Cabin in Madison

4.95 out of 5 average rating, 152 reviews

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.

Guest suite in Conway

4.98 out of 5 average rating, 494 reviews

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.

Cabin in Tamworth

4.99 out of 5 average rating, 147 reviews

Mountainside Retreat! Great Views! Cozy & Private!

Romantic Mountainside Cottage! A Cozy Escape with Wonderful Views of the Mountains. Very Private, Romantic & Luxurious stay in the Woods of NH. Fire Pit overlooking the mountains! Visit the town of Tamworth, head up to North Conway White Mountain's, or head south to the Lakes Region. All less than an hour away, then escape the traffic and retreat to the remote and quiet of your Mountain Cottage. We provide everything you will need for your stay, just bring a sense of adventure! Pets Yes!

Guest suite in Albany

4.88 out of 5 average rating, 409 reviews

Mountain Hideaway

Two private rooms with full bath in private home. Includes separate entrance sharing only a mud room. Downstairs room has a refrigerator, microwave, and toaster oven, coffee and tea provided. Located in a beautiful rural setting with mountain views adjacent to the National Forest and Tin mt conservation center. Only 1 mile from the Kancamangus Highway, route 16 and Conway. Minutes from outdoor activities: skiing, biking hiking, paddling and snowshoeing. Many restaurants and shops nearby.

Home in Albany

4.82 out of 5 average rating, 423 reviews

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!

Cabin in Conway

4.96 out of 5 average rating, 125 reviews

The Conscious Cabin

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 bath, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

Cottage in Parsonsfield

4.88 out of 5 average rating, 139 reviews

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.

Cabin in Madison

4.98 out of 5 average rating, 132 reviews

Gorgeous Log Cabin w/ Hot Tub & Fireplace

Escape to our secluded mountaintop log cabin, perfect for the whole family! Just a minute from King Pine Ski Area and 15 miles from North Conway, Bella Bear Cabin offers a truly unique retreat. With 2,500 sq ft of inviting space, you'll find a massive fireplace, an oversized master suite, two additional bedrooms, and a finished basement featuring twin-over-full bunk beds and a game room. Outside, unwind on three spacious decks and enjoy the pristine six-person hot tub.

Cottage in Brownfield

5 out of 5 average rating, 234 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Home in Madison

4.97 out of 5 average rating, 138 reviews

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.

Rental unit in Tamworth

4.89 out of 5 average rating, 158 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Madison vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Madison's top sights

King Pine Ski Area104 locals recommend

Hobbs Tavern & Brewing Company68 locals recommend

White Lake State Park34 locals recommend

Almost There Restaurant20 locals recommend

Rosie's Restaurant19 locals recommend

White Lake Speedway17 locals recommend

Other great vacation rentals in Madison

Cabin in Madison

4.93 out of 5 average rating, 72 reviews

Lakeside camp near North Conway

Cabin in Conway

4.98 out of 5 average rating, 84 reviews

Luxury Log Cabin in Conway Mount Washington Views

Cottage in Madison

4.97 out of 5 average rating, 62 reviews

Welcome to Lakota! A Cozy 2 BR Cottage.

Home in Madison

4.89 out of 5 average rating, 46 reviews

Beautiful, updated cozy cottage

Chalet in Madison

4.98 out of 5 average rating, 94 reviews

Breathtaking mountain views - Hidden gem!

Home in Madison

4.96 out of 5 average rating, 67 reviews

Waterfront property with hot tub near North Conway

Cabin in Madison

4.99 out of 5 average rating, 92 reviews

Mountain Living at the Little Bear Lodge!

Cabin in Madison

4.97 out of 5 average rating, 36 reviews

2 bedroom lake view cabin with private dock and AC

Quick stats about vacation rentals in Madison

Total rentals
200 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
6.7K reviews
Family-friendly rentals
180 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace

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 house rentals in Madison have wifi?
Absolutely! We offer over 110 house rentals with wifi in Madison. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly chalet rentals in Madison?
Madison has more than 20 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Madison?
Experience the best of Madison with our house rentals, starting at about $20 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 80 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 Chalet Rentals in Madison?
Enhance your stay in our Chalet Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with wifi, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore