Search Cottages in Madison

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 190 Cottages in Madison with updated reviews, rates, and availability.

Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities
Indoor pool, outdoor pool

Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities

9.8 out of 10, Exceptional, (286)
"Lovely visit to a quaint cottage in the white mountains. The host was wonderfully communicative and accommodating. "
Jackson NH Peaceful, Country Cottage / Access to Fabulous Amenities
Cozy Cottage on Lake Winni
Beach

Cozy Cottage on Lake Winni

9.2 out of 10, Wonderful, (33)
"This cabin was close to most attractions in the area. The cabin was clean and was perfect for our stay!"
Cozy Cottage on Lake Winni
Stunning lakefront gem with full water view, beach access & dock
TV

Stunning lakefront gem with full water view, beach access & dock

10.0 out of 10, Exceptional, (3)
"The house was kept very clean, great water views with access to shared dock and patio. We had a blast staying here. Amazing hosts, 10/10 recommend!"
Stunning lakefront gem with full water view, beach access & dock
Retreat near Conway : HotTub, Harry Potter Room
Miscellaneous

Retreat near Conway : HotTub, Harry Potter Room

9.6 out of 10, Exceptional, (4)
"I booked the location for a work retreat. We had a great time and would definitely book again."
Retreat near Conway : HotTub, Harry Potter Room
Mountain Views: Beautiful Nestlenook Farm Home!
Interior

Mountain Views: Beautiful Nestlenook Farm Home!

3.0 star property
10.0 out of 10, Exceptional, (3)
"We had the best time at this cozy little place. We were not sure what to expect as the pictures were from the summer and we went in December, but it was even prettier in the winter, all dressed up for Christmas. Perfect location, not too far from the shops and restaurants of Conway, and a 40 minute drive to Santa's Village. Comfy and clean-highly recommend!"
Mountain Views: Beautiful Nestlenook Farm Home!
Lake Wentworth - Wolfeboro, New Hampshire
Lake

Lake Wentworth - Wolfeboro, New Hampshire

9.6 out of 10, Exceptional, (80)
"Excellent property on a beautiful lake! The kids had a blast and there was so much space for sleeping and hanging out!"
Lake Wentworth - Wolfeboro, New Hampshire
Dog-friendly waterfront cottage with private dock, community beach, grill, W/D
Fridge, microwave, oven, stovetop

Dog-friendly waterfront cottage with private dock, community beach, grill, W/D

9.8 out of 10, Exceptional, (11)
"Great relaxing stay thank you!"
Dog-friendly waterfront cottage with private dock, community beach, grill, W/D
Maine Lakefront Cottage Rental with Sandy Beach
Property grounds

Maine Lakefront Cottage Rental with Sandy Beach

9.2 out of 10, Wonderful, (40)
"Loved the lake and location. Planning on stay again."
Maine Lakefront Cottage Rental with Sandy Beach
Peaceful lake front cottage w/large dock and sandy beach entry
Interior

Peaceful lake front cottage w/large dock and sandy beach entry

10.0 out of 10, Exceptional, (22)
"Everything was fantastic, definitely a place to inspire coming back. Host was very cooperative and easy to navigate the reservation with."
Peaceful lake front cottage w/large dock and sandy beach entry
Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!
Interior

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 SAR 687
SAR 2,080 total
includes taxes & fees
2 Jun - 3 Jun
Charming Jackson Cottage w/ hot tub & woodstove, minutes from skiing!
Charming lakefront 2-bedroom cottage with private beach & dock.
Fireplace

Charming lakefront 2-bedroom cottage with private beach & dock.

Charming lakefront 2-bedroom cottage with private beach & dock.
Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D
Outdoor dining

Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D

9.6 out of 10, Exceptional, (12)
"Bright and sunny, just as advertised. The kitchen could use a few more supplies but overall a good spot. We would book again. "
Two-story dog-friendly cabin with a wood stove, pool, tennis, beach, W/D
Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
On the beach, sun loungers

Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain

9.8 out of 10, Exceptional, (92)
"Great location, very quiet and relaxing"
The price is SAR 2,250
SAR 3,427 total
includes taxes & fees
29 May - 30 May
Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
Waterfront Cottage on Barker Pond
Smart TV

Waterfront Cottage on Barker Pond

2.0 star property
8.0 out of 10, Very Good, (1)
"My family thoroughly enjoyed the spot and thought it was pretty. "
Waterfront Cottage on Barker Pond
Secluded lakefront cottage with private beach LAKES REGION, DENMARK MAINE
Property grounds

Secluded lakefront cottage with private beach LAKES REGION, DENMARK MAINE

10.0 out of 10, Exceptional, (27)
"10/10 This property was just perfect. We travel to Maine annually and loved the proximity to the lake (just out the back door) and to town (approx 10 minutes) The owner was extremely responsive and the property lived up to the pictures, etc. A week here was extremely relaxing (even with 3 kids in tow!)"
Secluded lakefront cottage with private beach LAKES REGION, DENMARK MAINE
1 Block to Main Street: Wolfeboro Home w/ Fire Pit
Interior

1 Block to Main Street: Wolfeboro Home w/ Fire Pit

3.0 star property
1 Block to Main Street: Wolfeboro Home w/ Fire Pit
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Miscellaneous

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

10.0 out of 10, Exceptional, (12)
"Great for a quick trip with young swimmers! The dock was a great depth for jumping off over and over :-) "
The price is SAR 1,163
SAR 2,332 total
includes taxes & fees
29 May - 30 May
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro Lakehouse Retreat
Terrace/patio

Wolfeboro Lakehouse Retreat

8.0 out of 10, Very Good, (26)
"Awesome rustic property great for a family"
Wolfeboro Lakehouse Retreat
Cottage with great beach.
Property grounds

Cottage with great beach.

2.0 star property
10.0 out of 10, Exceptional, (3)
"We loved our stay at this cute, quaint cottage. The location was perfect just steps from Crescent lake and an easy kayak ride to Lake Wentwprth. Janis was very welcoming and the property was nice and clean. Will stay again! "
Cottage with great beach.
The Cowbell Cottage! Cozy, dog friendly & nestled in the Lakes Region of NH.
Microwave, oven, stovetop, dishwasher

The Cowbell Cottage! Cozy, dog friendly & nestled in the Lakes Region of NH.

10.0 out of 10, Exceptional, (2)
"Every year we come to the lake to take our kids to camp. It’s always just 2 nights, but we like staying in a house especially now that we have a dog. The Cowbell Cottage was perfect. It was so clean and nicely decorated. We had a lovely time. Ashley was a great host."
The Cowbell Cottage! Cozy, dog friendly & nestled in the Lakes Region of NH.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.