Madison Holiday Rentals

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Holiday Rentals in Madison

Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit

8.6 out of 10, Excellent, (60)
"We had a great time. The home was clean & space for 8woman was good. It’s was in a great spot close to NorthConway if you want to venture out. The price for the spot was good. The hill walking down to pond was steep. For young kids could be tricky. Wish the outside furniture was a little cleaner to sit on. We also couldn’t find any cleaning products to wipe down anything."
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit

Nordic Village Resort

3.0 star property
8.4 out of 10, Very good, (1648)
"It was such a nice and quiet place that was perfect for a weekend getaway to disconnect from the busy work week. Me and my partner couldn’t have found a better please to recharge and relax"
The price is AU$217
includes taxes & fees
1 Dec - 2 Dec
Nordic Village Resort

Attitash Mountain Village

3.0 star property
8.4 out of 10, Very good, (454)
"Always a good stay at Attitash. Clean condo with all the things we needed to cook with and be comfortable. "
The price is AU$194
includes taxes & fees
9 Dec - 10 Dec
Attitash Mountain Village

Pet-friendly Waterfront Cottage: On-site Bunkhouse

3.0 star property
Pet-friendly Waterfront Cottage: On-site Bunkhouse

Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

8.8 out of 10, Excellent, (19)
"Great time."
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

Updated Chalet - Private Setting - 5 Mi from Storyland

9.6 out of 10, Exceptional, (119)
"Very roomy and comfortable. "
Updated Chalet - Private Setting - 5 Mi from Storyland

Fabulous Mountain View Chalet close to Everything in North Conway. Pet Friendly

9.6 out of 10, Exceptional, (124)
"The house was great and had a beautiful view on the deck. Quiet neighborhood and very close to everything. It was a good size house for myself, husband & 2 kids. And my husband’s parents too. We enjoyed echo lake, the muddy moose, the train station and so much more! Overall, a great time! "
Fabulous Mountain View Chalet close to Everything in North Conway. Pet Friendly

Dog-friendly home with foosball table, deck, grill, wood stove and gas fireplace

9.0 out of 10, Wonderful, (32)
"This was an awesome house in a quiet serene wooded neighborhood. Large space and will definitely go back!"
Dog-friendly home with foosball table, deck, grill, wood stove and gas fireplace

Two-story charming retreat w/deck, private gas grill, and private washer/dryer

9.4 out of 10, Exceptional, (76)
"My husband and I stayed here for a quick vacation after our wedding and it was the perfect relaxing house for the two of us. It was very quiet and comfortable while still very close to anything we wanted to see/do/eat. We loved our stay!"
The price is AU$474
includes taxes & fees
28 Nov - 29 Nov
Two-story charming retreat w/deck, private gas grill, and private washer/dryer

Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach

9.4 out of 10, Exceptional, (74)
"Cabin was very clean, and well stocked, neighborhood was nice and very easy to get to, enjoyed our stay very much, we will be back"
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach

Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities

9.8 out of 10, Exceptional, (276)
"Great for enjoying fall foliage and cog railway."
Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities

Lovely home with water view, hot tub, fireplace, & washer/dryer

8.8 out of 10, Excellent, (25)
"Outstanding views. Convenient location. Nicely appointed. Spacious enough for 8 adults and 6 children with opportunities for privacy. Excellent game room. Towels more than plentiful. However, odd that there was not enough glassware to go around. Would rate experience A plus but for one serious shortcoming. The fence in front of property is not secure and potentially hazardous for families with young children."
Lovely home with water view, hot tub, fireplace, & washer/dryer

Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

6.8 out of 10, (9)
"I didn’t look close at the on-line pics so at first arrival I had concerns. It’s a charming older style lake house that could use a bit of pampering but it was very clean and comfortable for our group of 8. The host and management company were great and easy to communicate with. We came up for our daughter’s wedding and we all had a very nice weekend. Thank you"
Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

Pet Friendly, Quiet Neighborhood, Cozy lower level cabin

9.8 out of 10, Exceptional, (76)
"Very spacious and cozy cabin! Marianne was very accommodating. She responded very quickly to all emails. The cabin was very clean. We would love to stay again when we're in the Conway area."
The price is AU$415
includes taxes & fees
26 Nov - 27 Nov
Pet Friendly, Quiet Neighborhood, Cozy lower level cabin

New listing - Beautiful Spacious Custom Log Cabin.

10.0 out of 10, Exceptional, (82)
"So clean, just right for our family "
New listing - Beautiful Spacious Custom Log Cabin.

Two-story home w/guest suite, gas grill, & private washer/dryer - Dogs okay

9.4 out of 10, Exceptional, (65)
"Couch was really dirty . Dog hair all over the futon. Mold and mildew smell all over the house . Upon leaving the house we cleaned the whole house . The person who came to clean the house was rude , gave an attitude about check out process . "
Two-story home w/guest suite, gas grill, & private washer/dryer - Dogs okay

Newly Renovated Rustic Cabin

9.6 out of 10, Exceptional, (253)
"Nice cozy cabin very beautiful inside"
Newly Renovated Rustic Cabin

Fido Friendly Indoor Heated Pool Slps 16 Pool Table Swim SkiTubeSnowboardRelax

9.4 out of 10, Exceptional, (12)
"Great place for our Friendsgiving weekend. The kids loved the pool! Close to echo lake/cathedral ledge and Conway center. Hosts were very responsive to any questions/issues I had. Would definitely stay again."
Fido Friendly Indoor Heated Pool Slps 16 Pool Table Swim SkiTubeSnowboardRelax

Dog-friendly, waterfront home on the Saco River with private hot tub & fireplace

9.2 out of 10, Wonderful, (37)
"Amazing location! Loved being right on the river and close to great hiking. We really enjoyed our stay, looking forward to going back"
Dog-friendly, waterfront home on the Saco River with private hot tub & fireplace

Updated Chalet - Private Setting - 5 Mi From Storyland

9.8 out of 10, Exceptional, (139)
"Came for a girls shopping weekend and had a wonderful stay. The unit was very cozy, clean and comfortable. The check in process was easy and the location was ideal. Would definitely stay here again!!"
Updated Chalet - Private Setting - 5 Mi From Storyland
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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Other types of properties in Madison you may be interested in

Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit

8.6 out of 10, Excellent, (60)
"We had a great time. The home was clean & space for 8woman was good. It’s was in a great spot close to NorthConway if you want to venture out. The price for the spot was good. The hill walking down to pond was steep. For young kids could be tricky. Wish the outside furniture was a little cleaner to sit on. We also couldn’t find any cleaning products to wipe down anything."
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit

Hampton Inn & Suites North Conway

2.5 star property
8.2 out of 10, Very good, (1009)
"I loved "
The price is AU$169
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites North Conway

Green Granite Inn, Ascend Hotel Collection

2.5 star property
7.2 out of 10, Good, (1240)
"Everything you need is at this hotel for a reasonable price "
The price is AU$94
includes taxes & fees
26 Nov - 27 Nov
Green Granite Inn, Ascend Hotel Collection
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Nordic Village Resort: This holiday home rental outside of Madison is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Amenities such as a coffee maker and free parking are also available for your convenience. You and your friends and family can relax into your holiday with amenities such as an outdoor tennis court. Our travellers also rate Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit as a favourite home for rent in Madison.

How many holiday rentals are there in Madison?

Expedia has 47 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 Kahuna Laguna, or get out into nature at a spot like Saco River. King Pine Ski Area and Ossipee Lake are a couple of places you'll find in the wider area.

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.