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

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Madison cottages

A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

1. 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 CA $201
CA $249 total
includes taxes & fees
Nov 2 - Nov 3
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
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
The price is CA $301
CA $657 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Tuftonboro Escape: Steps to Private Beaches!
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 CA $215
CA $533 total
includes taxes & fees
Oct 22 - Oct 23
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
9.6 out of 10, Exceptional, (14 reviews)
"Great place "
United States
Anonymous traveller
The price is CA $200
CA $247 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $243
CA $484 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Lakehouse near N. Conway Beach Access, Canoe, Fire Pit, Grill & Pool Table
A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

6. 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 CA $217
CA $268 total
includes taxes & fees
Oct 19 - Oct 20
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A rustic cabin with a wooden exterior, a red deck, and a stone wall garden.

7. 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.
The price is CA $296
CA $946 total
includes taxes & fees
Nov 9 - Nov 10
Charming Jackson Cottage w/ hot tub & woodstove!
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, (8 reviews)
"Had a great time at the cottages at Wolfeboro. Nice and relaxing stay for 2 nights"
United States
Connie S.
The price is CA $220
CA $271 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is CA $196
CA $244 total
includes taxes & fees
Nov 3 - Nov 4
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.
The price is CA $227
CA $282 total
includes taxes & fees
Nov 3 - Nov 4
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
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
The price is CA $283
CA $344 total
includes taxes & fees
Nov 15 - Nov 16
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
A cabin with a deck, surrounded by trees.

12. Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
The price is CA $250
CA $597 total
includes taxes & fees
Oct 27 - Oct 28
Riverside Cottage • Fireplace • Mountain Views
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 CA $242
CA $580 total
includes taxes & fees
Oct 20 - Oct 21
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.
The price is CA $299
CA $366 total
includes taxes & fees
Oct 18 - Oct 19
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

Holiday Inn Express North Conway by IHG

Holiday Inn Express North Conway by IHG

8/10 Good
"The location of the hotel is great. Cross the street is the outlet mall and Market Basket. Nearby have various restaurants. The hotel itself was renovated last year so looks very new. Inside hallway and room are very clean. Staff are very friendly and helpful. Breakfast is okay. The only thing we don’t like is the loud noise when you flush the toilet, especially at night when people are sleeping. Otherwise it’s a very good stay."
Jun 2-night trip
Posted 2 hours ago
Holiday Inn Express North Conway by IHG

Find out more about Madison

Madison Cottages information

Number of reviews
193
Accommodation
191 Cottages
Lowest Price
CA $244
Highest Price
CA $946

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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