Madison Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Madison holiday rentals

Dining
White Mountains Waterfront Chalet w/ Private Beach

White Mountains Waterfront Chalet w/ Private Beach

White Mountains Waterfront Chalet w/ Private Beach
Eidelweiss Village
9.8 out of 10, Exceptional, (25)
"We stayed here the weekend of June 20th for a girls trip & had an amazing time! The home was clean and comfortable. We enjoyed the private beach & beautiful view from the deck! Highly recommend. "
United States
Erin B.
The price is HK$1,575
HK$3,692 total
includes taxes & fees
6 Jan - 7 Jan 2026
White Mountains Waterfront Chalet w/ Private Beach
Coffee and/or coffee maker
TuckAway Suites at East Branch

TuckAway Suites at East Branch

TuckAway Suites at East Branch
2.5 star property
Intervale
10.0 out of 10, Exceptional, (11)
"Stayed in Alpine Suite. Super clean and lovely sitting area with armchairs and fireplace. Just perfect 😊 "
Australia
Diane
The price is HK$928
HK$1,556 total
includes taxes & fees
12 Jan - 13 Jan 2026
TuckAway Suites at East Branch
Free WiFi
White Mountain Cottages

White Mountain Cottages

White Mountain Cottages
3.0 star property
North Conway
7.6 out of 10, Good, (106)
"Beautiful views and great price! Simple but met all our needs. "
United States
Alex
The price is HK$560
HK$608 total
includes taxes & fees
29 Dec - 30 Dec
White Mountain Cottages
Interior
998 Pinhkham · Cozy Wooded Cabin/private hot tub/fireplace/river

998 Pinhkham · Cozy Wooded Cabin/private hot tub/fireplace/river

998 Pinhkham · Cozy Wooded Cabin/private hot tub/fireplace/river
jackson
9.6 out of 10, Exceptional, (63)
"Quiet, private cabin with cozy decor. Hot tub was great! Close to hiking at Pinkham Notch. "
United States
susan
The price is HK$793
HK$1,494 total
includes taxes & fees
12 Jan - 13 Jan 2026
998 Pinhkham · Cozy Wooded Cabin/private hot tub/fireplace/river
2 bedrooms, desk, WiFi, bed sheets
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake

Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Lovell
10.0 out of 10, Exceptional, (5)
"Very nice stay. Perfect for a couple of adults. "
United States
Joann M.
The price is HK$856
HK$1,797 total
includes taxes & fees
5 Jan - 6 Jan 2026
Historic, luxurious 2 bed 2 bath private suite in Lovell, 10 mins to Kezar Lake
Fridge, microwave, oven, stovetop
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Conway
10.0 out of 10, Exceptional, (91)
"Great place in a nice location. We stayed one night on our way up to Maine. Marianne’s place was perfect. She welcomed us and our pup making for a nice experience. Thanks!"
United States
Erich L.
The price is HK$972
HK$1,882 total
includes taxes & fees
4 Jan - 5 Jan 2026
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Fridge, microwave, oven, stovetop
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Brownfield
10.0 out of 10, Exceptional, (3)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
The price is HK$1,195
HK$2,463 total
includes taxes & fees
6 Jan - 7 Jan 2026
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Property grounds
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro
10.0 out of 10, Exceptional, (17)
"All excellent "
United States
Marc
The price is HK$1,372
HK$3,539 total
includes taxes & fees
5 Jan - 6 Jan 2026
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Exterior
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
Freedom
8.8 out of 10, Excellent, (31)
"It was great and the weather was perfect. Love that it’s dog friendly! And Helen was very helpful. "
United States
ELIZABETH B T.
The price is HK$778
HK$2,211 total
includes taxes & fees
3 Jan - 4 Jan 2026
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
Dining
Ava Jade yurt nestled in the woods of Brownfield, Maine

Ava Jade yurt nestled in the woods of Brownfield, Maine

Ava Jade yurt nestled in the woods of Brownfield, Maine
Brownfield
10.0 out of 10, Exceptional, (17)
"The ava jade yurt was a great spot to unwind. It had everything we needed, was clean, and very comfy in the winter weather. Communication was good and the check-in and check-out processes were easy. "
United States
Sean M.
The price is HK$856
HK$1,272 total
includes taxes & fees
28 Dec - 29 Dec
Ava Jade yurt nestled in the woods of Brownfield, Maine
Terrace/patio
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4)
"We had a perfect stay. Super cute cabin, clean and very comfortable.We thoroughly enjoyed or time there. Very easy process and would absolutely recommend and book again."
United States
Jessica G.
The price is HK$1,426
HK$1,766 total
includes taxes & fees
30 Dec - 31 Dec
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Property grounds
Rufus III Yurt on the river

Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (12)
"We enjoyed our stay very much!"
United States
Sandy D.
The price is HK$1,089
HK$1,458 total
includes taxes & fees
6 Jan - 7 Jan 2026
Rufus III Yurt on the river
Fridge, microwave, oven, stovetop
85 Dundee · Cozy Log Cabin/Private Hot Tub/Brook/Fireplace

85 Dundee · Cozy Log Cabin/Private Hot Tub/Brook/Fireplace

85 Dundee · Cozy Log Cabin/Private Hot Tub/Brook/Fireplace
Jackson
9.4 out of 10, Exceptional, (22)
"Perfect get away! Hosts were very reliable and easy to get ahold of! Cabin was in great condition, so was yard space and the town nearby was INCREDIBLE! Will definitely be back! "
United States
Samantha G.
The price is HK$848
HK$1,595 total
includes taxes & fees
8 Jan - 9 Jan 2026
85 Dundee · Cozy Log Cabin/Private Hot Tub/Brook/Fireplace
Outdoor spa tub
Attitash Mountain Village

Attitash Mountain Village

Attitash Mountain Village
3.0 star property
Bartlett
8.6 out of 10, Excellent, (547)
"The staff was very polite and very helpful. The rooms were amazing and cozy. We certain will be back "
United States
Chelsey
The price is HK$1,323
HK$1,435 total
includes taxes & fees
7 Jan - 8 Jan 2026
Attitash Mountain Village
Exterior
Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access

Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access

Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access
2.0 star property
Newfield
10.0 out of 10, Exceptional, (3)
"I stayed here for the 4th of July weekend and had a wonderful time! You can really tell the host put a lot of thought and detail to every little thing on the inside and outside. There was a lot of nice features throughout like the hidden sauna, hot tub, fire pit, swinging chairs, etc. "
United States
Stephanie S.
The price is HK$1,898
HK$3,382 total
includes taxes & fees
19 Jan - 20 Jan 2026
Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access
Gazebo
Nordic Village Resort

Nordic Village Resort

Nordic Village Resort
3.0 star property
Jackson
8.6 out of 10, Excellent, (1799)
"It is nice place to stay. "
United States
Wen
The price is HK$894
HK$970 total
includes taxes & fees
25 Dec - 26 Dec
Nordic Village Resort
Interior
Family & dog friendly ski chalet with fire pit

Family & dog friendly ski chalet with fire pit

Family & dog friendly ski chalet with fire pit
Bartlett
9.0 out of 10, Wonderful, (2)
The price is HK$933
HK$2,932 total
includes taxes & fees
14 Jan - 15 Jan 2026
Family & dog friendly ski chalet with fire pit
Pool
Cozy Stays for the Holiday in Cabin Style Condo near all amenities @ attractions

Cozy Stays for the Holiday in Cabin Style Condo near all amenities @ attractions

Cozy Stays for the Holiday in Cabin Style Condo near all amenities @ attractions
Intervale
10.0 out of 10, Exceptional, (5)
"We had an amazing time at Boo Bear Cabin. Joey was an amazing attentive host. One of the best I have dealt with in my experience with VRBO. House theme was adorable and fitting for NH. Balcony views were amazing and pool access is just foot steps away. Perfect spot for a relaxing family vacation. We can’t wait to book again! "
United States
Jocelyn B.
The price is HK$1,043
HK$2,491 total
includes taxes & fees
26 Dec - 27 Dec
Cozy Stays for the Holiday in Cabin Style Condo near all amenities @ attractions
Terrace/patio
Allie Mae Yurt nestled in the woods

Allie Mae Yurt nestled in the woods

Allie Mae Yurt nestled in the woods
Brownfield
10.0 out of 10, Exceptional, (21)
"Beautiful property! Comfortable and clean lodging. "
United States
Ian M.
The price is HK$933
HK$1,356 total
includes taxes & fees
25 Dec - 26 Dec
Allie Mae Yurt nestled in the woods
Exterior
Danforth Bay Camping and RV Resort

Danforth Bay Camping and RV Resort

Danforth Bay Camping and RV Resort
2.0 star property
Freedom
8.4 out of 10, Very good, (15)
"Family- friendly Beautiful all around Soo many things to do you can never get bored Enjoyed every minute of it "
United States
Roxanna
Danforth Bay Camping and RV Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison Hotel Reviews

Fairfield Inn & Suites By Marriott North Conway

Fairfield Inn & Suites By Marriott North Conway

10/10 Excellent
"Great room! Amazing area and delicious breakfast."
Kimberly 2-night trip
Posted 2 days ago
Fairfield Inn & Suites By Marriott North Conway

Find out more about Madison

Search for holiday rentals in Madison on Expedia! You can easily find your home rentals, villas, holiday apartments in Madison using one of the methods below:

  • View our selection of featured holiday rentals in Madison
  • Use the map to find apartments and other holiday homes in the Madison neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Madison while they last

Look no further and take a look at our great range of rental properties in Madison!

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay. Madison is known for its shopping and ski areas. Make sure you have time to check out the lake views and restaurants during your trip.

What are some of the best holiday rentals that Madison has to offer?

Birchmont Townhouses: This holiday home rental outside Madison is located near skiing, and offers a BBQ, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Madison?

Expedia has 52 holiday rentals for your stay in Madison.

What’s there to see and do in Madison?

Explore the area and family-friendly sights such as Conway Station, or get out into nature at a spot like Silver Lake. King Pine Ski Area and Ossipee Pine Barrens Preserve are other places to visit while you're in town.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family gatherings.