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

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Madison cottages

A deck with a table and chairs, a red umbrella, and a grill.

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

Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
Bartlett
The price is AU$510
includes taxes & fees
17 Sept - 18 Sept
Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
A cabin with a porch, a small attached shed, and a well-maintained lawn.

2. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, 2, (2 reviews)
"We’ll kept "
United States
Denise
The price is AU$645
includes taxes & fees
4 Oct - 5 Oct
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.

3. 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, 6, (6 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is AU$276
includes taxes & fees
15 Sept - 16 Sept
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.

4. 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, 20, (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.
The price is AU$673
includes taxes & fees
15 Sept - 16 Sept
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
A garden with a white pergola, red chairs, and pink flowers.

5. 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, 12, (12 reviews)
"Great place "
United States
Anonymous traveller
The price is AU$284
includes taxes & fees
6 Oct - 7 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
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, 120, (120 reviews)
"We had a great stay and was a nice place to enjoy the area."
United States
Jason B.
The price is AU$943
includes taxes & fees
17 Sept - 18 Sept
Charming Jackson Cottage w/ hot tub & woodstove!
A Story Land sign with a brick pathway leading to colorful buildings with distinct architectural styles.

7. Riverside Cottage • Private Beach • Mountain Views

Riverside Cottage • Private Beach • Mountain Views
Bartlett
The price is AU$552
includes taxes & fees
15 Sept - 16 Sept
Riverside Cottage • Private Beach • Mountain Views
A riverside cabin with a view of the river and surrounding trees.

8. Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
The price is AU$521
includes taxes & fees
27 Sept - 28 Sept
Riverside Cottage • Fireplace • Mountain Views
A waterfront area with a large white building, a dock with boats, and a clock tower in the background.

9. 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, 5, (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.
The price is AU$305
includes taxes & fees
15 Sept - 16 Sept
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

10. 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, 20, (20 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is AU$286
includes taxes & fees
22 Sept - 23 Sept
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A lakeside view with boats, a deck, and an American flag.

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

Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
Moultonborough
9.8 out of 10, 102, (102 reviews)
"Great location, very quiet and relaxing"
United States
Thiago S.
The price is AU$1,364
includes taxes & fees
12 Oct - 13 Oct
Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
A house with a porch, surrounded by a garden with pink and yellow flowers.

12. 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, 7, (7 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is AU$248
includes taxes & fees
15 Sept - 16 Sept
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

13. 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, 4, (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
The price is AU$394
includes taxes & fees
15 Sept - 16 Sept
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
A garden with a white pergola, red chairs, and pink flowers.

14. 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, 4, (4 reviews)
"Everything was great!"
United States
Leah F.
The price is AU$415
includes taxes & fees
15 Sept - 16 Sept
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.

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, 3, (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 AU$389
includes taxes & fees
15 Sept - 16 Sept
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 Lodge At Jackson Village

The Lodge At Jackson Village

10/10 Excellent
"great spot... just needs a bar.."
Richard 3-night trip
Posted 1 hour ago
The Lodge At Jackson Village

Find out more about Madison

Madison Cottages information

Number of reviews
181
Accommodation
194 Cottages
Lowest Price
AU$248
Highest Price
AU$1,364

Frequently asked questions

What is there to do in Madison near my cottage?
There are plenty of superb things to fill your days in Madison. Make tracks to big attractions like King Pine Ski Area, M&D Playhouse and Tuckerman Brewery. The Barnstormers Theatre, Madison Boulder Natural Area and Remick Country Doctor Museum and Farm are other must-do's.

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