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In two weeks
Oct 24 - Oct 26
In two months
Dec 5 - Dec 7
In three months
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In four months
Jan 30 - Feb 1

Cottages in Madison

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Property grounds

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

10.0 out of 10, Exceptional, (16)
"Great for a quick trip with young swimmers! The dock was a great depth for jumping off over and over :-) "
The price is ￥40,821
￥86,942 total
includes taxes & fees
Oct 15 - Oct 16
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Terrace/patio

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

10.0 out of 10, Exceptional, (4)
"Great location & comfortable! "
The price is ￥28,167
￥34,827 total
includes taxes & fees
Oct 13 - Oct 14
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Terrace/patio

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

9.6 out of 10, Exceptional, (10)
"Great property. Loved our stay and the owners were great! Definitely will book again "
The price is ￥32,453
￥39,970 total
includes taxes & fees
Oct 14 - Oct 15
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!
Exterior

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

9.8 out of 10, Exceptional, (111)
"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! "
The price is ￥29,246
￥85,702 total
includes taxes & fees
Nov 4 - Nov 5
Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Exterior

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

10.0 out of 10, Exceptional, (4)
"It was very cute and clean, loved the outside area and would def be back again."
The price is ￥32,453
￥39,970 total
includes taxes & fees
Oct 16 - Oct 17
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Terrace/patio

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

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."
The price is ￥34,290
￥42,454 total
includes taxes & fees
Oct 19 - Oct 20
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Terrace/patio

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

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."
The price is ￥32,453
￥39,970 total
includes taxes & fees
Oct 13 - Oct 14
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Terrace/patio

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

10.0 out of 10, Exceptional, (3)
"Everything was great!"
The price is ￥45,924
￥56,226 total
includes taxes & fees
Oct 13 - Oct 14
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Exterior

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

10.0 out of 10, Exceptional, (15)
"I love and have had a couple decades of Lake Winnepesaukee summers. With my boys now grown and raising their own families in other parts of the country, I drove up for a couple days, by myself, for a Lake Winni fix. The on site cottage was perfect in terms of location, privacy, cleanliness and the unspoken presence of security that was important to me a line traveler. I highly recommend this Inn for a special week on the lake, couples, small families. Accommodations are beautifully updated and...
The price is ￥34,086
￥42,069 total
includes taxes & fees
Oct 13 - Oct 14
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
Exterior

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

9.4 out of 10, Exceptional, (3)
"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!!"
The price is ￥44,699
￥54,569 total
includes taxes & fees
Oct 13 - Oct 14
Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Exterior

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

10.0 out of 10, Exceptional, (2)
"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."
The price is ￥45,924
￥56,226 total
includes taxes & fees
Oct 13 - Oct 14
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
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

North Conway Grand Hotel

North Conway Grand Hotel

10/10 Excellent
"The staff and room was great! The breakfast buffet was wonderful!!!"
Kimberley 1-night trip
Posted 2 days ago
North Conway Grand Hotel

Find out more about Madison

Madison Cottages information

Number of reviews
153
Accommodation
193 Cottages
Lowest Price
￥34,827
Highest Price
￥86,942

Frequently asked questions

Why book your cottage in Madison with Expedia?
Expedia has some superb cottages in Madison, so get set for an unforgettable vacation 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.