Search Cottages in Madison

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Madison cottages

Terrace/patio

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, (11 reviews)
"Great place "
United States
Anonymous traveller
The price is €153
includes taxes & fees
10 Jun - 11 Jun
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
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
Wolfeboro
10.0 out of 10, Exceptional, (18 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is €176
includes taxes & fees
10 Jun - 11 Jun
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Exterior

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, (18 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 €532
includes taxes & fees
6 Jul - 7 Jul
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Exterior

Riverside Cottage w/Deck, Bath, King Bed, & Electric Fire

Riverside Cottage w/Deck, Bath, King Bed, & Electric Fire
Bartlett
Riverside Cottage w/Deck, Bath, King Bed, & Electric Fire
Property grounds

Lakefront Cottage with Private Dock and Kayaks. Dog-Friendly

Lakefront Cottage with Private Dock and Kayaks. Dog-Friendly
Newfield
8.6 out of 10, Excellent, (7 reviews)
"A very enjoyable stay!"
United States
Dougl G.
The price is €575
includes taxes & fees
24 Jun - 25 Jun
Lakefront Cottage with Private Dock and Kayaks. Dog-Friendly
Exterior

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 €611
includes taxes & fees
29 Jun - 30 Jun
Charming Jackson Cottage w/ hot tub & woodstove!
Golf

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, (6 reviews)
"Cute place just close quarters "
United States
Rylee F.
The price is €162
includes taxes & fees
10 Jun - 11 Jun
Cottage 11 - Year Round - Pet Friendly - 1 Bed / 1 Bath w/ Private Courtyard
Exterior

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 €209
includes taxes & fees
17 Jun - 18 Jun
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Property grounds

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
8.8 out of 10, Excellent, (6 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is €150
includes taxes & fees
8 Jun - 9 Jun
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Exterior

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 €236
includes taxes & fees
8 Jun - 9 Jun
Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Marina

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 €178
includes taxes & fees
10 Jun - 11 Jun
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Exterior

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, (2 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 €295
includes taxes & fees
22 Jun - 23 Jun
Cottage 1-2 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Property grounds

Riverside cottage w/Deck, Bespoke Decor & Near Attractions & Skiing

Riverside cottage w/Deck, Bespoke Decor & Near Attractions & Skiing
Bartlett
Riverside cottage w/Deck, Bespoke Decor & Near Attractions & Skiing
Exterior

Riverside cottage w/deck, King Bed, BBQ & fireplace

Riverside cottage w/deck, King Bed, BBQ & fireplace
Bartlett
The price is €408
includes taxes & fees
1 Jul - 2 Jul
Riverside cottage w/deck, King Bed, BBQ & fireplace
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
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
The price is €329
includes taxes & fees
22 Jun - 23 Jun
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
House (6 Bedrooms) | Interior

1 Mi to Main St Fryeburg: Historic Family Home

1 Mi to Main St Fryeburg: Historic Family Home
3.0 star property
Fryeburg
1 Mi to Main St Fryeburg: Historic Family Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

The White Mountain Hotel & Resort

The White Mountain Hotel & Resort

10/10 Excellent
"The White Mountain Inn was exactly the peaceful escape we needed. The property has a beautiful 9‑hole golf course that wasn’t crowded at all, and even if you don’t bring your own clubs, they have rentals ready to go. The grounds are incredibly relaxing, with stunning views of the mountains that make you want to slow down and breathe for a moment. Dinner at the resort was fantastic, and we loved enjoying drinks in the bar both before and after our meal. The atmosphere made it easy to unwind — we even made new friends during our stay, which added to the charm of the trip. With both of us having very busy, stressful jobs, this getaway felt restorative in every way. The staff was amazing, the setting was peaceful, and the whole experience was exactly what we hoped for."
Jennifer 1-night trip
Posted 7 hours ago
The White Mountain Hotel & Resort

Find out more about Madison

Madison Cottages information

Number of reviews
1
Accommodation
195 Cottages
Lowest Price
€395
Highest Price
€2,380

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.