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

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
Oct 25 - Oct 26
Total with taxes and fees
Cozy Tuftonboro Escape: Steps to Private Beaches!
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

2. 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
$163 nightly
The price is $177
Oct 25 - Oct 26
Total with taxes and fees
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
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, (14 reviews)
"Great place "
United States
Anonymous traveler
$163 nightly
The price is $177
Oct 25 - Oct 26
Total with taxes and fees
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A riverside cabin with a view of the river and surrounding trees.

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

Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
Bartlett
10.0 out of 10, Exceptional, (1 review)
$374 nightly
The price is $406
Oct 27 - Oct 28
Total with taxes and fees
Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
A lakeside house with a dock, a small boathouse, and a flag.

5. Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table

Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
Brownfield
10.0 out of 10, Exceptional, (6 reviews)
"Great little camp with lake access! Thanks for hosting us :-)"
United States
Anonymous traveler
$324 nightly
The price is $354
Nov 2 - Nov 3
Total with taxes and fees
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
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, (124 reviews)
"We had a great stay and was a nice place to enjoy the area."
United States
Jason B.
$615 nightly
The price is $667
Oct 26 - Oct 27
Total with taxes and fees
Charming Jackson Cottage w/ hot tub & woodstove!
A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

7. 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
9.8 out of 10, Exceptional, (22 reviews)
"This is a great place to stay with a dog"
United States
David M.
$173 nightly
The price is $188
Oct 25 - Oct 26
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.

8. 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, (9 reviews)
"Had a great time at the cottages at Wolfeboro. Nice and relaxing stay for 2 nights"
United States
Connie S.
$177 nightly
The price is $192
Oct 25 - Oct 26
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.

9. 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, (8 reviews)
"Great location & comfortable! "
United States
Jeanine L.
$160 nightly
The price is $174
Oct 25 - Oct 26
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.

10. Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath

Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (5 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.
$183 nightly
The price is $198
Oct 26 - Oct 27
Total with taxes and fees
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A riverside cabin with a view of the river and surrounding trees.

11. Riverside Cottage • Private Beach • Mountain Views

Riverside Cottage • Private Beach • Mountain Views
Bartlett
$374 nightly
The price is $406
Oct 27 - Oct 28
Total with taxes and fees
Riverside Cottage • Private Beach • Mountain Views
A riverside cabin with a view of the river and surrounding trees.

12. Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
$380 nightly
The price is $412
Oct 27 - Oct 28
Total with taxes and fees
Riverside Cottage • Fireplace • Mountain Views
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.
$255 nightly
The price is $277
Oct 25 - Oct 26
Total with taxes and fees
Cottage 8-9 - Year Round - Pet Friendly $50 Fee- 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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Top Madison Hotel Reviews

North Conway Mountain Inn

North Conway Mountain Inn

10/10 Excellent
"wonderful"
Chunguang 1-night trip
Posted 1 hour ago
North Conway Mountain Inn

Find out more about Madison

Madison Cottages information

Number of reviews
190
Accommodation
191 Cottages
Lowest Price
$174
Highest Price
$667

Frequently asked questions

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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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