Madison Holiday Rentals

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Holiday Rentals in Madison

Indoor pool, a heated pool
Indoor Heated Pool Sleeps 16 Pool Table Swim Ski Tube Snowboard Shop Relax Enjoy
10.0 out of 10, Exceptional, (5)
"Very lovely home to have a family gathering"
Indoor Heated Pool Sleeps 16 Pool Table Swim Ski Tube Snowboard Shop Relax Enjoy
Exterior
Pet Friendly, Quiet Neighborhood, Cozy lower level cabin
10.0 out of 10, Exceptional, (60)
"Our host Marianne made our stay very relaxing. She is very accommodating and very responsive. We like to hike with our dog. The property is located near several hiking trails with varying degrees of difficulty. Our pup loved it. The cabin was also comfortable enough for us to leave him behind for a short time while we went out for some shopping. We would recommend this property to anyone with a pup who enjoys the outdoors but also likes quiet at night. "
The price is NZ$381
includes taxes & fees
28 May - 29 May
Pet Friendly, Quiet Neighborhood, Cozy lower level cabin
Indoor pool, outdoor pool
Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities
9.8 out of 10, Exceptional, (253)
"We really enjoyed staying at this little cottage. We have been coming to the Jackson area for years, and it was great to find this place that had everything we needed. We especially appreciated the proximity to the Memorial Hospital which we ended up having to visit while we were there. I have never met such nice people at a hospital. Linda was a great host who went over and above what we expected. We will be back again!"
Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities
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Private kitchen
Newly Renovated Rustic Cabin
9.8 out of 10, Exceptional, (243)
"Nicely finished home with comfortable amenities. Suggest a deep clean and updated kitchenware. Comfortable beds."
Newly Renovated Rustic Cabin
TV, fireplace, books
Lakefront home with private beach & dock - close to skiing
9.8 out of 10, Exceptional, (54)
"Came for a long weekend in the the winter for fun winter activities. We really enjoyed the nice kitchen (could use a better quality cutting board), large dining room table, comfy chairs and couch with lots of cozy blankets, and most of all the spectacular view out over the lake! As other have said, the distribution of beds/rooms is a bit unusual, with only one queen bed in its own room, and the other queen in an open loft, and no bathroom on the main floor, but it still worked out great for our...
Lakefront home with private beach & dock - close to skiing
Private kitchen
Updated Chalet - Private Setting - 5 Mi From Storyland
9.8 out of 10, Exceptional, (118)
"Perfect place a a ski reunion with old friends to ski in the valley, close proximity to North Conway, quiet neighborhood with all the amenities you would need. Very enjoyable experience."
Updated Chalet - Private Setting - 5 Mi From Storyland
Fridge, microwave, oven, stovetop
Lakefront home on Ossipee Lake with dock and gorgeous views
9.8 out of 10, Exceptional, (9)
"We loved the house and the view. Everything was perfect"
Lakefront home on Ossipee Lake with dock and gorgeous views
Interior
Grand Blanc Mountain Home
9.8 out of 10, Exceptional, (81)
"Overall, what an amazing place, Well kept and very clean. Internet was kind of unreliable, didn't reach a lot of places but we made due. Biggest complaint, I reached out by text to 2 different numbers but never got a response. They weren't big issues, but still. I've been renting thru VRBO for many years and this is by far my family's favorite."
Grand Blanc Mountain Home
Property grounds
Centrally located condo with pools, hot tubs, tennis, skating, & skiing access
9.8 out of 10, Exceptional, (7)
"We just loved our stay at Nordic wilderness. It was clean and comfortable. Beds were super cozy! Very spacious (group of 9) and had everything we needed. Wed def stay again."
Centrally located condo with pools, hot tubs, tennis, skating, & skiing access
Smart TV, fireplace, DVD player, books
Updated Chalet - Private Setting - 5 Mi from Storyland
9.6 out of 10, Exceptional, (98)
"Place was clean and comfy"
Updated Chalet - Private Setting - 5 Mi from Storyland
Property grounds
Fabulous Mountain View Chalet close to Everything in North Conway. Pet Friendly
9.6 out of 10, Exceptional, (104)
"The house is very nice and I wouldn’t mind living there , The best thing about it is the view from the deck, of the mountains and the valley it’s incredible! We all had a very enjoyable time being there for the week 😃 My communication back-and-forth with Terry was pleasant and my questions were answered very quickly. Had a great overall experience!"
Fabulous Mountain View Chalet close to Everything in North Conway. Pet Friendly
Fridge, microwave, oven, stovetop
Two-story charming retreat w/deck, private gas grill, and private washer/dryer
9.6 out of 10, Exceptional, (62)
"We enjoyed a nice stay at the property. Clean, great location and had everything we needed for a 3 night stay. Property is managed through a rental service so asking questions and having access to the owner wasn't the easiest. Overall a great time, would stay again."
The price is NZ$456
includes taxes & fees
20 May - 21 May
Two-story charming retreat w/deck, private gas grill, and private washer/dryer
Fridge, microwave, oven, stovetop
Two-story home w/guest suite, gas grill, & private washer/dryer - Dogs okay
9.6 out of 10, Exceptional, (59)
"We loved the house and how close it was to so many fun activities. The house was warm and inviting."
Two-story home w/guest suite, gas grill, & private washer/dryer - Dogs okay
Private kitchen
Family Friendly Rustic Newly Renovated Cabin Abutting The White Lake State Park.
9.6 out of 10, Exceptional, (233)
"Wonderful place! Clean, close to all the stuff you’d want to go to in the lakes region. Absolutely with it!"
Family Friendly Rustic Newly Renovated Cabin Abutting The White Lake State Park.
Exterior
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
9.4 out of 10, Exceptional, (70)
"We stayed in excellent VRBO rentals before. Only problem was garbage from previous rentals had never been removed from property. As snow melted we found an old cigar but on deck as well as dog poop. Which we picked up ourselves. The were many different conflicting instructions on what not to do and what to do in regards to heat, water, dishwasher (there is no dishwasher), but there were pods for one? Otherwise, we had fun. Would recommend streamlining instructions, and removing trash as we had...
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
Fridge, microwave, oven, stovetop
Dog-friendly home with foosball table, deck, grill, wood stove and gas fireplace
9.2 out of 10, Wonderful, (17)
"This was a perfect house in a perfect location! We had plenty of space to spread out - bedrooms across 3 different levels of the home, and a very cozy main level for hanging out together. We loved that this location is close to the best attractions in the White Mountains, but just off the beaten path making it easy to access and more relaxing. Overall our visit was great and we would absolutely return to this home again!"
Dog-friendly home with foosball table, deck, grill, wood stove and gas fireplace
TV, fireplace, DVD player, books
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
9.0 out of 10, Wonderful, (51)
"Great!"
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
Interior
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
9.0 out of 10, Wonderful, (16)
"Great time."
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
Exterior
Dog-friendly, waterfront home on the Saco River with private hot tub & fireplace
9.0 out of 10, Wonderful, (25)
"Great property and location. House was very clean and cozy."
Dog-friendly, waterfront home on the Saco River with private hot tub & fireplace
Beach
Cozy Cottage on Lake Winni
9.0 out of 10, Wonderful, (27)
"We enjoyed our stay. Great location on the water with a dock for our boat. We loved that we could bring our dog. It was as advertised. Cabin on the water. We are happy with our stay."
Cozy Cottage on Lake Winni
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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.

Other types of properties in Madison you may be interested in

Exterior
Residence Inn by Marriott, North Conway
3.0 star property
9.4 out of 10, Exceptional, (1000)
"This was centrally located near my family I was visiting and food/shopping. The room was very spacious and quiet. It’s always nice when breakfast is included!"
The price is NZ$224
includes taxes & fees
27 May - 28 May
Residence Inn by Marriott, North Conway
TV, fireplace, DVD player, books
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
9.0 out of 10, Wonderful, (51)
"Great!"
Renovated waterfront home near skiing with lake view, 3 kayaks, dock & firepit
Exterior
Swiss Chalets Village Inn
2.0 star property
8.4 out of 10, Very good, (1001)
"Very clean and convenient to restaurants and shops in N. Conway. A 20 minute drive to the Kancamagus hwy and a 40 minute drive to Franconia notch. Would definitely stay here again "
The price is NZ$119
includes taxes & fees
19 May - 20 May
Swiss Chalets Village Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Madison holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Madison. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Madison. Seeing all the best attractions is bound to make you fall in love with Madison. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Madison short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Madison?

Expedia has 59 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 White Lake State Park. King Pine Ski Area and Saco River 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.

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