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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Guest favorite

Guest suite in Conway

4.99 out of 5 average rating, 419 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.

Sep 18 – 23

G$25,695 GYD per night

Guest favorite

Cabin in Madison

4.95 out of 5 average rating, 114 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.

Dec 13 – 20

G$48,712 GYD per night

Guest favorite

Cabin in Conway

4.95 out of 5 average rating, 294 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.

Feb 19 – 26

G$27,695 GYD per night

Guest favorite

Guesthouse in Conway

4.97 out of 5 average rating, 123 reviews

Private, quiet contemporary studio apartment.

Experience the glory of the seasons from our newly remodeled studio apartment nestled in the woods of New Hampshire’s White Mountains. The apartment has its own private entrance, clean, modern furnishings with a soft contemporary color scheme. We live at the end of a 2.8 mile state designated scenic dirt/gravel road, on 50 acres with a beaver pond, relaxing spaces and colorful gardens. All of this is within 20 minutes of North Conway's shopping and its' majestic mountains, lakes and rivers.

Mar 9 – 16

G$25,426 GYD per night

Guest favorite

Apartment in Tuftonboro

4.97 out of 5 average rating, 267 reviews

Apartment CenterTuftonboro minutes from Wolfeboro

This is a spacious lower- level apartment 1000 sq ft in our home . Our guests will have complete privacy with convenience parking . It features a large master bedroom and cozy second bed room. You have a large private kitchen , living room , a bathroom and laundry room . Our area offers many activities as well as shopping in historic down town Wolfeboro. A very short drive to all the best things that Lake Winnipesaukee offers. Please read all our description before booking . Thanks so much

Nov 12 – 19

G$30,375 GYD per night

Guest favorite

Guest suite in Albany

4.89 out of 5 average rating, 361 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.

Dec 27 – Jan 3

G$21,661 GYD per night

Guest favorite

Home in Albany

4.81 out of 5 average rating, 370 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!

Oct 4 – 11

G$15,633 GYD per night

Guest favorite

Apartment in Campton

4.92 out of 5 average rating, 166 reviews

White Mountain is a Special Place

Renovated modern farmhouse studio in the White Mountains. We are the 4th generation in our family’s home. Posts and beams with new kitchen, shiplap, hardwood floors, and large bathroom, and great view overlooking the fields. 36 acres of field, woods, and cut your Christmas Tree here. If lucky you will catch a glimpse of the horses in the field. Close to hiking, skiing, and lakes. Waterville Valley 9 miles, Loon Mtn. 15 miles. Owls Nest Golf Couse. Private entry /private studio.

Aug 13 – 20

G$19,482 GYD per night

Guest favorite

Cabin in Madison

4.98 out of 5 average rating, 112 reviews

Gorgeous Log Cabin w/ Hot Tub & Fireplace

Bring the entire family and escape to our secluded mountaintop log cabin. Just 1 min. from King Pine Ski Area and 15 miles from North Conway, Bella Bear Cabin is a one-of-a-kind retreat. Enjoy 2,500 sq ft of space, a massive fireplace, oversized master suite, 2 additional bedrooms, and a finished basement with twin over full bunk beds and a game room. Outside, three separate decks await, along with a pristine six-person hot tub. Don't miss this unforgettable escape!

Mar 17 – 24

G$72,084 GYD per night

Guest favorite

Cottage in Brownfield

5.0 out of 5 average rating, 210 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.

May 27 – Jun 3

G$24,730 GYD per night

Guest favorite

Guesthouse in Brownfield

4.88 out of 5 average rating, 379 reviews

Mountain Treehouse Guesthouse

Spacious 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.

Jun 1 – 8

G$23,362 GYD per night

Guest favorite

Guest suite in Conway

5.0 out of 5 average rating, 256 reviews

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.

Jun 8 – 15

G$22,568 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Madison vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Madison's top sights

Rosie's Restaurant19 locals recommend

Songbird6 locals recommend

Community Market & Deli13 locals recommend

Dollar General3 locals recommend

White Lake Speedway17 locals recommend

Madison Boulder Natural Area10 locals recommend

Other great vacation rentals in Madison

Guest favorite

Cabin in Tamworth

4.99 out of 5 average rating, 104 reviews

Mountainside Retreat! Great Views! Cosy & Private!

Jun 13 – 20

G$36,430 GYD per night

Guest favorite

Guest suite in Woodstock

4.99 out of 5 average rating, 141 reviews

The Birches - Riverside Suite with a View

Jun 1 – 8

G$19,325 GYD per night

Guest favorite

Guest suite in Bridgton

4.98 out of 5 average rating, 165 reviews

Barn on Pleasant-walk to town

Mar 22 – 29

G$32,119 GYD per night

Superhost

Cottage in Freedom

4.78 out of 5 average rating, 440 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Oct 22 – 29

G$30,459 GYD per night

Superhost

Apartment in Porter

4.86 out of 5 average rating, 318 reviews

The Carriage House Apartment

Dec 31 – Jan 7

G$26,229 GYD per night

Guest favorite

Condo in Woodstock

4.91 out of 5 average rating, 246 reviews

Luxury Studio Jacuzzi Pool White Mtns. Riverfront

Jan 13 – 20

G$26,928 GYD per night

Guest favorite

Guest suite in Gorham

4.97 out of 5 average rating, 322 reviews

Cozy comfort close to White Mountain attractions!

Mar 22 – 29

G$18,264 GYD per night

Guest favorite

Apartment in Jackson

4.97 out of 5 average rating, 502 reviews

Studio, pet friendly, river views, Jackson NH

Feb 19 – 26

G$30,419 GYD per night

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Other great vacation rentals in Madison

Guest favorite

Cottage in Dalton

4.97 out of 5 average rating, 125 reviews

Sunny Cottage on Private Lake

Apr 1 – 8

G$27,186 GYD per night

Guest favorite

Loft in Woodstock

4.98 out of 5 average rating, 174 reviews

The Loft at North House

Feb 3 – 10

G$26,735 GYD per night

Guest favorite

Apartment in Whitefield

4.96 out of 5 average rating, 134 reviews

Hikers perfect spot.

Jul 15 – 22

G$16,780 GYD per night

Guest favorite

Apartment in Campton

4.93 out of 5 average rating, 418 reviews

The White Mountain Oaks retreat-ski, hike, relax

Dec 19 – 26

G$22,955 GYD per night

Guest favorite

Cottage in Brownfield

4.86 out of 5 average rating, 127 reviews

Tompeca Cottage - Pet Friendly

Oct 31 – Nov 7

G$23,227 GYD per night

Guest favorite

Cabin in Albany

4.92 out of 5 average rating, 51 reviews

Cozy, Dog Friendly Cabin on Swift Brook!

Dec 12 – 19

G$23,851 GYD per night

Guest favorite

Home in Madison

5.0 out of 5 average rating, 23 reviews

Beautiful, updated cozy cottage

Aug 19 – 26

G$34,941 GYD per night

Guest favorite

Cabin in Madison

4.95 out of 5 average rating, 21 reviews

2 bedroom lake view cabin with private dock and AC

Mar 30 – Apr 6

G$35,811 GYD per night

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Quick stats about vacation rentals in Madison

Total rentals
190 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
160 properties are a good fit for families
Total number of reviews
6.1K reviews
Nightly prices starting at
G$6,255 GYD before taxes and fees

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 80 vacation rentals for guests traveling with pets.
Are there Madison vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Madison, available on Airbnb. Make a splash and soak up the sun in style!
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.
Are there family-friendly house rentals in Madison?
Madison has more than 90 family-friendly house 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 $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Madison have air conditioning?
Absolutely! We offer over 70 house 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.

Madison vacation rentals

Top-rated vacation rentals in Madison

Vacation rentals for every style

Cabins

Houses

Chalets

Popular amenities for Madison vacation rentals

Stay near Madison's top sights

Other great vacation rentals in Madison

Cabin in Tamworth

Guest suite in Woodstock

Guest suite in Bridgton

Cottage in Freedom

Apartment in Porter

Condo in Woodstock

Guest suite in Gorham

Apartment in Jackson

Other great vacation rentals in Madison

Cottage in Dalton

Loft in Woodstock

Apartment in Whitefield

Apartment in Campton

Cottage in Brownfield

Cabin in Albany

Home in Madison

Cabin in Madison

Quick stats about vacation rentals in Madison

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Madison?

Are there pet-friendly vacation rentals in Madison?

Are there Madison vacation rentals on Airbnb with pools?

Do house rentals in Madison have wifi?

Are there family-friendly house rentals in Madison?

How much does it cost to stay in house rentals in Madison?

Do house rentals in Madison have air conditioning?

Do house rentals in Madison have a bbq area?

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