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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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.
The price is £145
includes taxes & fees
21 Oct - 22 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A single-story house with a chimney, a front porch, and a small garden area.

2. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
The price is £345
includes taxes & fees
13 Oct - 14 Oct
Lake Winnipesaukee Home for Fall & Winter Fun
A black wooden building with a white window, a chimney, and a small garden area with mulch and a yellow object.

3. 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)
The price is £281
includes taxes & fees
22 Oct - 23 Oct
Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
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 traveller
The price is £135
includes taxes & fees
19 Oct - 20 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
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)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
The price is £253
includes taxes & fees
2 Nov - 3 Nov
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, (122 reviews)
"We had a great stay and was a nice place to enjoy the area."
United States
Jason B.
The price is £509
includes taxes & fees
28 Oct - 29 Oct
Charming Jackson Cottage w/ hot tub & woodstove!
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

7. 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
The price is £135
includes taxes & fees
25 Oct - 26 Oct
Cottage 3 - Year Round - Pet Friendly $50 Fee - 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.
The price is £680
includes taxes & fees
13 Oct - 14 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.

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, (7 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is £132
includes taxes & fees
25 Oct - 26 Oct
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A cabin with a deck, surrounded by trees.

10. Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
The price is £302
includes taxes & fees
19 Oct - 20 Oct
Riverside Cottage • Fireplace • Mountain Views
A waterfront area with a large white building, a dock with boats, and a clock tower in the background.

11. 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.
The price is £152
includes taxes & fees
26 Oct - 27 Oct
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A cabin with a porch, a small attached shed, and a well-maintained lawn.

12. 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
The price is £348
includes taxes & fees
28 Oct - 29 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
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
The price is £301
includes taxes & fees
20 Oct - 21 Oct
Riverside Cottage • Private Beach • Mountain Views
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
The price is £197
includes taxes & fees
13 Oct - 14 Oct
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
A garden with a white pergola, red chairs, and pink flowers.

15. 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.
The price is £209
includes taxes & fees
13 Oct - 14 Oct
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

8/10 Good
"The outside of the hotel is great, inside the rooms show age. The room had fantastic view of fall colors and had a balcony. Overall it was adequate for us."
Srivaths 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
£132
Highest Price
£680

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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