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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 cottages

Exterior
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$1,194
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$3,538 total
includes taxes & fees
5 Jan - 6 Jan 2026
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Terrace/patio
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard

Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard

Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (5)
"Booked a last minute trip with the family and it was perfect. Right near downtown and a cozy place to rest with the kids."
United States
Sean P.
The price is HK$1,183
HK$1,460 total
includes taxes & fees
14 Jan - 15 Jan 2026
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
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
Terrace/patio
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4)
"Great location & comfortable! "
United States
Jeanine L.
The price is HK$1,183
HK$1,460 total
includes taxes & fees
1 Jan - 2 Jan 2026
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Exterior
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (17)
"Very nice spot nice get away would stay there again"
United States
Alan T.
The price is HK$1,284
HK$1,587 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Terrace/patio
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4)
"Everything was great!"
United States
Leah F.
The price is HK$1,951
HK$2,387 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Exterior
Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!

Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!

Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!
Jackson
9.8 out of 10, Exceptional, (112)
"We had a great stay at this charming Jackson home for New Year’s Eve! The house was very clean and everything we could need was provided. We enjoyed the amazing hot tub and cozy wood stove. The owner was so nice and helpful and made check in/out very easy! We loved staying here! "
United States
Maura P.
The price is HK$1,731
HK$4,679 total
includes taxes & fees
14 Jan - 15 Jan 2026
Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!
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

Residence Inn by Marriott, North Conway

Residence Inn by Marriott, North Conway

10/10 Excellent
"excelent"
miryam 2-night trip
Posted 13 hours ago
Residence Inn by Marriott, North Conway

Find out more about Madison

Madison Cottages information

Number of reviews
153
Accommodation
192 Cottages
Lowest Price
HK$1,460
Highest Price
HK$4,679

Frequently asked questions

Why book your cottage in Madison with Expedia?
Expedia has some superb cottages in Madison, so get set for an unforgettable holiday on nature's doorstep. If you're on a budget, select how much you're willing to spend and the star rating of your property. Or, make use of our filters to search for cottages with a pool or a hot tub. We'll help you find the perfect place whatever your style of travel or plans.
How can I find cheap cottages in Madison?
A wonderful way to track down cheap cottages in Madison is with Expedia's user-friendly filter tool. Tailor your search results by budget, star rating and amenities to discover awesome rates in just a few keystrokes.
What is there to do in Madison near my cottage?
The ideal travel accessory is a well-planned itinerary. King Pine Ski Area is a good place to begin your exploration of Madison.

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