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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Madison cottages

A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

1. 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 5 - Oct 6
Total with taxes and fees
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
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, Exceptional, (2 reviews)
"We’ll kept "
United States
Denise
$426 nightly
The price is $462
Oct 5 - Oct 6
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.

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, 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 $176
Nov 3 - Nov 4
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.

4. 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
9.4 out of 10, Exceptional, (13 reviews)
"Great place "
United States
Anonymous traveler
$163 nightly
The price is $176
Oct 6 - Oct 7
Total with taxes and fees
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A black wooden building with a white window, a chimney, and a small garden area with mulch and a yellow object.

5. 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)
$343 nightly
The price is $372
Oct 22 - Oct 23
Total with taxes and fees
Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
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, (122 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 27 - Oct 28
Total with taxes and fees
Charming Jackson Cottage w/ hot tub & woodstove!
A house with a porch, surrounded by a garden with pink and yellow flowers.

7. 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.
$158 nightly
The price is $171
Oct 25 - Oct 26
Total with taxes and fees
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A lakeside view with boats, a deck, and an American flag.

8. 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, Exceptional, (103 reviews)
"Great location, very quiet and relaxing"
United States
Thiago S.
$831 nightly
The price is $902
Oct 12 - Oct 13
Total with taxes and fees
Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
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, 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 25 - Oct 26
Total with taxes and fees
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A cabin with a deck, surrounded by trees.

10. Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
$356 nightly
The price is $386
Oct 15 - Oct 16
Total with taxes and fees
Riverside Cottage • Fireplace • Mountain Views
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

11. 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
$239 nightly
The price is $259
Oct 5 - Oct 6
Total with taxes and fees
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
A single-story house with a chimney, a front porch, and a small garden area.

12. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
$422 nightly
The price is $458
Oct 13 - Oct 14
Total with taxes and fees
Lake Winnipesaukee Home for Fall & Winter Fun
A Story Land sign with a brick pathway leading to colorful buildings with distinct architectural styles.

13. Riverside Cottage • Private Beach • Mountain Views

Riverside Cottage • Private Beach • Mountain Views
Bartlett
$382 nightly
The price is $414
Oct 14 - Oct 15
Total with taxes and fees
Riverside Cottage • Private Beach • Mountain Views
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, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
$253 nightly
The price is $275
Oct 5 - Oct 6
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

Swiss Chalets Village Inn

Swiss Chalets Village Inn

10/10 Excellent
"The Swiss Chalets Village was a great choice for our one-night stay! The room was on the smaller side, but it was spotless, very clean, and came equipped with everything we needed for a comfortable night. The absolute highlight was relaxing on the balcony with a beautiful view of the mountains. Topped off with convenient parking right near our unit and a nice breakfast in the morning, it was a wonderful, hassle-free experience. Highly recommend!"
Igor 1-night trip
Posted 3 hours ago
Swiss Chalets Village Inn

Find out more about Madison

Madison Cottages information

Number of reviews
284
Accommodation
192 Cottages
Lowest Price
$171
Highest Price
$902

Frequently asked questions

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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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