A lake surrounded by dense forest and mountains in the background.

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Our top choices for Madison cottages

Riverside Cottage • Private Beach • Mountain Views

Riverside Cottage • Private Beach • Mountain Views
Bartlett
The price is ¥36,125
¥82,391 total
includes taxes & fees
Jul 29 - Jul 30
Riverside Cottage • Private Beach • Mountain Views

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is ¥43,847
¥54,147 total
includes taxes & fees
Aug 25 - Aug 26
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath

House w/ Balcony ~ 5 Mi to Cranmore Resort!

House w/ Balcony ~ 5 Mi to Cranmore Resort!
3.0 star property
Glen
The price is ¥44,698
¥113,692 total
includes taxes & fees
Aug 9 - Aug 10
House w/ Balcony ~ 5 Mi to Cranmore Resort!

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (12 reviews)
"Great place "
United States
Anonymous traveler
The price is ¥42,170
¥52,332 total
includes taxes & fees
Jul 30 - Jul 31
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

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, (19 reviews)
"We had a wonderful stay at Grandma’s with our two little boys and dog. It was clean, cozy and a perfect location for our weekend ice fishing trip! We enjoyed walking the rail trail, watching ducks by the dock, passing snowmobiles, and playing puzzles/games. Highly recommend for a family getaway. We would definitely stay again."
United States
Nicole C.
The price is ¥53,212
¥105,879 total
includes taxes & fees
Aug 25 - Aug 26
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Quiet Lake Retreat with Fireplace and short walk to the beach

Quiet Lake Retreat with Fireplace and short walk to the beach
Moultonborough
10.0 out of 10, Exceptional, (6 reviews)
"Cute house, went last minute. Temperatures were in the negative which was great for Castle in the Clouds, just down the road as it was dead!Must be a super fun place in the summer "
United States
Amy D.
Quiet Lake Retreat with Fireplace and short walk to the beach

Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
The price is ¥36,575
¥82,878 total
includes taxes & fees
Aug 26 - Aug 27
Riverside Cottage • Fireplace • Mountain Views

Charming Jackson Cottage w/ hot tub & woodstove!

Charming Jackson Cottage w/ hot tub & woodstove!
Jackson
9.8 out of 10, Exceptional, (119 reviews)
"We had a great stay and was a nice place to enjoy the area."
United States
Jason B.
The price is ¥57,930
¥138,934 total
includes taxes & fees
Aug 1 - Aug 2
Charming Jackson Cottage w/ hot tub & woodstove!

Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside

Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
Bartlett
The price is ¥40,114
¥79,231 total
includes taxes & fees
Aug 20 - Aug 21
Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"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 ¥28,752
¥35,641 total
includes taxes & fees
Jul 29 - Jul 30
Cottage 10 - 1 Bedroom w/ Loft / 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
9.0 out of 10, Wonderful, (7 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is ¥42,596
¥52,616 total
includes taxes & fees
Aug 2 - Aug 3
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

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, (19 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is ¥39,590
¥48,995 total
includes taxes & fees
Aug 2 - Aug 3
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit

Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Wolfeboro
9.4 out of 10, Exceptional, (3 reviews)
"The two connected Cottages were Perfect for myself husband & teenage daughter. Loved the private outdoor space & firepit! Onsite manager was super accessible and really helpful! Will definitely be back!!"
United States
Dorenda W.
The price is ¥42,383
¥52,563 total
includes taxes & fees
Jul 29 - Jul 30
Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit

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
9.8 out of 10, Exceptional, (8 reviews)
"Cute place just close quarters "
United States
Rylee F.
The price is ¥38,975
¥48,154 total
includes taxes & fees
Aug 2 - Aug 3
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard

Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit

Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Wolfeboro
10.0 out of 10, Exceptional, (3 reviews)
"In addition to everything this property offers we found there was a nearby 12mile bike trail that goes through the woods passing lakes on the the route, and bikes were available at the property."
United States
Justin
The price is ¥49,624
¥61,664 total
includes taxes & fees
Aug 18 - Aug 19
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit

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 reviews)
"Everything was great!"
United States
Leah F.
The price is ¥52,574
¥64,859 total
includes taxes & fees
Aug 25 - Aug 26
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
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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Frequently asked questions

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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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