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

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Madison cottages

A cabin with a porch, a small attached shed, and a well-maintained lawn.

1. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (2 reviews)
"We’ll kept "
United States
Denise
$426 nightly
The price is $462
Aug 31 - Sep 1
Total with taxes and fees
Cozy Tuftonboro Escape: Steps to Private Beaches!
A cabin with a deck, a large window, and a view of a lake at sunset.

2. Riverside Cottage • Private Beach • Mountain Views

Riverside Cottage • Private Beach • Mountain Views
Bartlett
$396 nightly
The price is $430
Aug 31 - Sep 1
Total with taxes and fees
Riverside Cottage • Private Beach • Mountain Views
A garden with a white pergola, red chairs, and pink flowers.

3. Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (12 reviews)
"Great place "
United States
Anonymous traveler
$216 nightly
The price is $234
Sep 1 - Sep 2
Total with taxes and fees
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

4. Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (6 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
$212 nightly
The price is $230
Aug 26 - Aug 27
Total with taxes and fees
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A log cabin with a snow-covered roof, a front porch, and a garage.

5. 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, (20 reviews)
"We had the best time here, would 100% go back. Very quiet and relaxing and the hosts were great."
United States
The F.
$593 nightly
The price is $643
Sep 1 - Sep 2
Total with taxes and fees
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
A rustic cabin with a wooden exterior, a red deck, and a stone wall garden.

6. Charming Jackson Cottage w/ hot tub & woodstove!

Charming Jackson Cottage w/ hot tub & woodstove!
Jackson
9.8 out of 10, Exceptional, (120 reviews)
"We had a great stay and was a nice place to enjoy the area."
United States
Jason B.
$658 nightly
The price is $714
Sep 8 - Sep 9
Total with taxes and fees
Charming Jackson Cottage w/ hot tub & woodstove!
A riverside cabin with a view of the river and surrounding trees.

7. Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
$395 nightly
The price is $429
Aug 31 - Sep 1
Total with taxes and fees
Riverside Cottage • Fireplace • Mountain Views
A cabin with a deck, a red umbrella, and a small garden.

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

Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
Bartlett
$422 nightly
The price is $458
Sep 8 - Sep 9
Total with taxes and fees
Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

9. Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (20 reviews)
"This is a great place to stay with a dog"
United States
David M.
$196 nightly
The price is $212
Sep 15 - Sep 16
Total with taxes and fees
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A golf course with a pond, surrounded by trees with autumn foliage.

10. Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard

Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (8 reviews)
"Cute place just close quarters "
United States
Rylee F.
$193 nightly
The price is $209
Sep 15 - Sep 16
Total with taxes and fees
Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard
A house with a porch, surrounded by a garden with pink and yellow flowers.

11. Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
9.0 out of 10, Wonderful, (7 reviews)
"Great location & comfortable! "
United States
Jeanine L.
$184 nightly
The price is $200
Sep 15 - Sep 16
Total with taxes and fees
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A waterfront area with a large white building, a dock with boats, and a clock tower in the background.

12. Cottage 10 - Pet Friendly $50 Fee - 1 Bedroom w/ Loft / 1 Bath

Cottage 10 - Pet Friendly $50 Fee - 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.
$221 nightly
The price is $239
Sep 15 - Sep 16
Total with taxes and fees
Cottage 10 - Pet Friendly $50 Fee - 1 Bedroom w/ Loft / 1 Bath
A garden with a white pergola, red chairs, and pink flowers.

13. Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
$276 nightly
The price is $299
Sep 1 - Sep 2
Total with taxes and fees
Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

14. Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath

Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
Wolfeboro
9.6 out of 10, Exceptional, (4 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
$269 nightly
The price is $292
Sep 9 - Sep 10
Total with taxes and fees
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

15. Cottage 5-6 - Year Round Pet Friendly $50 Fee- 2 Bedroom / 1 Bath End Unit

Cottage 5-6 - Year Round Pet Friendly $50 Fee- 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.
$269 nightly
The price is $292
Sep 9 - Sep 10
Total with taxes and fees
Cottage 5-6 - Year Round Pet Friendly $50 Fee- 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

The Green Granite North Conway, an Ascend Collection Hotel

The Green Granite North Conway, an Ascend Collection Hotel

10/10 Excellent
"The breakfast was delicious and many choices. The pool was beautiful."
Cheryl 2-night trip
Posted less than an hour ago
The Green Granite North Conway, an Ascend Collection Hotel

Find out more about Madison

Madison Cottages information

Number of reviews
86
Accommodation
192 Cottages
Lowest Price
$200
Highest Price
$714

Frequently asked questions

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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.

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