Holiday Rentals in Madison

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Madison

White Mountain Cottages

3.0 star property
8.0 out of 10, Very good, (34)
"Cute little cottage. Love the fireplace. "
The price is €140
includes taxes & fees
13 Mar - 14 Mar
White Mountain Cottages

Nordic Village Resort

3.0 star property
8.4 out of 10, Very good, (1673)
"We love the Nordic and will come back sometime soon! "
The price is €155
includes taxes & fees
2 Mar - 3 Mar
Nordic Village Resort

Attitash Mountain Village

3.0 star property
8.6 out of 10, Excellent, (479)
"The lodging was fantastic nice and clean. "
The price is €111
includes taxes & fees
23 Mar - 24 Mar
Attitash Mountain Village

Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities

9.8 out of 10, Exceptional, (281)
"My wife and I had a lovely time. We booked the weekend to enjoy so quiet time, went to the pool house a few times for the hot tub (inside and out were both lovely) the only issue was we had was a left over food snack we found on the floor in the bedroom. Easily fixed, but my wife wasn’t pleased about that.Overall a wonderful stay, the heater works very very well, good water pressure, the kitchen is stocked with gadgets, we mostly drank tea and ate leftovers, went to the 110 grill for dinner...
Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities

Abbott Brook Chalet B - Private Setting - 5 Mi from Storyland

9.6 out of 10, Exceptional, (126)
"Our family of 4 stayed at the Abbott Brook in the Chalet B and it was the perfect place to stay. The chalet was well stocked, clean and very cute. The host Richard was fantastic to work with as his responses were quick and pleasant. The location is perfect for those wanting to go to Cranmore Mountain and visit North Conways main drag. We would definitely stay here again. "
Abbott Brook Chalet B - Private Setting - 5 Mi from Storyland

Fido Friendly Indoor Heated Pool Slps 22 Pool Table Swim SkiGambleSnowboardRelax

9.4 out of 10, Exceptional, (21)
"Our stay was just perfect. Plenty of room . Pool was perfect warm and inviting. Kids Loved it! House was charming. Beautiful fire place. Very clean. Host was super quick to reply. We Loved it all. "
Fido Friendly Indoor Heated Pool Slps 22 Pool Table Swim SkiGambleSnowboardRelax

New listing - Beautiful Spacious Custom Log Cabin.

10.0 out of 10, Exceptional, (89)
"Had a great time staying at this house with a large group for a ski trip. "
New listing - Beautiful Spacious Custom Log Cabin.

Wanderwell House

2.5 star property
The price is €217
includes taxes & fees
17 Mar - 18 Mar
Wanderwell House

Pine Brook Lodge: pool table, AC, sauna, fireplaces, internet, bar, walk to town

10.0 out of 10, Exceptional, (154)
"Our host was amazing and super responsive. The house had a great mountain cabin feeling to it. The game room was incredible; it kept our crew entertained, no need to go out into town. The Sauna was the best, especially after a full day of snowboarding. It slept 12 of us very comfortably"
Pine Brook Lodge: pool table, AC, sauna, fireplaces, internet, bar, walk to town

4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

9.0 out of 10, Wonderful, (8)
"The house was clean and comfortable. It was roomy. The views were great. The owners were helpful and friendly. We would stay here again. "
4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

Grand Blanc Mountain Home

9.8 out of 10, Exceptional, (91)
"From the very first trip. To now our 4th visit. Our closest friends and family have rented this home and every time it never disappoints. If you are looking to be off the grid and have the amenities of a hotel, but also be close to a major town if needing something. Look no further. This is the home you should rent. The best!"
Grand Blanc Mountain Home

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

9.8 out of 10, Exceptional, (153)
"Had a great time on family ski trip. Good location. Owner was great to work with. Nice and clean place. Kids and parents enjoyed. Owner goes out of his way to make it nice, comfortable and willing to address any concerns. "
The price is €544
includes taxes & fees
30 Mar - 31 Mar
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

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

8.8 out of 10, Excellent, (19)
"It’s no wonder that the house resides on Paradise Drive. An absolute slice of heaven. This was our second time staying here and we can’t wait to book again. You can’t beat the location when you are a short walk to the lively public beach while also sitting on a cool quiet tributary with a private dock. The home is clean and comfortable with multiple wall mounted AC units to escape the summer heat. Two bedrooms with plenty of space for air mattresses makes this place great for families or...
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet

Cozy Retreat near Ossipee Lake, sleeps 8, pet friendly!

9.8 out of 10, Exceptional, (17)
"Great spot, rural but with just the right amenities not too far. Bonus that the local (walking distance) lake was frozen over for some nice walks"
Cozy Retreat near Ossipee Lake, sleeps 8, pet friendly!

Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

10.0 out of 10, Exceptional, (50)
"We were a group of 10 adults from several states (some friends, some family) celebrating a milestone birthday. Brian’s house fit the bill perfectly for our group. While we stayed during winter, we enjoyed the great views across the frozen lake and many of the great activities at the house (pool, ping pong, Nintendo) We spent much of our time cooking together and just visiting with each other. The kitchen was nicely stocked and there was the perfect amount of room for our group to dine...
Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

North Conway 5 Bedroom 3 Bathroom 3 Living Rooms close to Downtown

9.8 out of 10, Exceptional, (41)
"We have stayed at this house on multiple visits to North Conway. We love this house. "
North Conway 5 Bedroom 3 Bathroom 3 Living Rooms close to Downtown

Beautiful North Conway Chalet in Cathedral Ledge with 4 Bedrooms and 1.5 Bath

8.6 out of 10, Excellent, (11)
"Check out the bunk beds they are sick! The couch upstairs extends so cool! The neighborhood was cool, look for the bear statue. The arcade game was good! (Reviewed by my 8 year old) "
Beautiful North Conway Chalet in Cathedral Ledge with 4 Bedrooms and 1.5 Bath

Rustic ski chalet in the heart of North Conway off West Side Road

10.0 out of 10, Exceptional, (23)
"My family had the best time this week! The house was very clean, and had all the amenities of home with a rustic, mountain feel. The owner was extremely responsive and we didn’t want for anything the entire stay. Definitely recommend!"
Rustic ski chalet in the heart of North Conway off West Side Road

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

9.8 out of 10, Exceptional, (78)
"We had a great time! Very Cozy home, perfect for a weekend away in the mountains. Easy access to the center of town with lots to do in the area. The apartment was beautifully decorated, very clean, and had everything we needed and then some. Marianne was available for any questions and was very thoughtful. Great spot to venture out from to explore. "
The price is €236
includes taxes & fees
2 Mar - 3 Mar
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

NH Country Retreat Family Reunions & Weddings

9.8 out of 10, Exceptional, (46)
"This home was even more beautiful than the pictures suggested. We loved every moment of our stay. The trails from the property were stunning, and we hope to come back in the future :)"
NH Country Retreat Family Reunions & Weddings
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.
Don't see what you're looking for?
See all available properties in Madison
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Madison you may be interested in

Purity Spring Resort

2.0 star property
8.8 out of 10, Excellent, (144)
"Location near King pine ski hill was perfect. We stayed in the Queen+Twin bed room. It was located in the building with the restaurant, which was super convenient to not have to bundle up/drive to get dinner! The view out the back windows was forest, which was nice. Very clean. Comfy beds and modern linens/comforters. A little dated, but I would definitely stay here again!!"
The price is €97
includes taxes & fees
18 Mar - 19 Mar
Purity Spring Resort

North Conway Grand Hotel

4.0 star property
8.4 out of 10, Very good, (1010)
"Need coffee station during the whole day"
The price is €150
includes taxes & fees
2 Mar - 3 Mar
North Conway Grand Hotel

Green Granite Inn, Ascend Hotel Collection

2.5 star property
7.0 out of 10, Good, (1190)
"Obviously an older property that probably needs a complete refurb. But has been taken well care of in the interim. I booked a room with bunk beds and for two queens. I didn't bother to request we change. Altogether nice hotel for the price. I'd probably stay here again. "
The price is €61
includes taxes & fees
12 Mar - 13 Mar
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.

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.

How many holiday rentals are there in Madison?

Expedia has 48 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.