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

Search Madison Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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
Sep 11 - Sep 12
Total with taxes and fees
Cozy Tuftonboro Escape: Steps to Private Beaches!
A deck with a table and chairs, a red umbrella, and a grill.

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

Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
Bartlett
$351 nightly
The price is $381
Sep 17 - Sep 18
Total with taxes and fees
Tree-Lined Cottage • Wood Fireplace • Ellis River • Private Firepit • Riverside
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, (12 reviews)
"Great place "
United States
Anonymous traveler
$183 nightly
The price is $198
Sep 8 - Sep 9
Total with taxes and fees
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A house with a porch, surrounded by a garden with pink and yellow flowers.

4. 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.
$172 nightly
The price is $186
Sep 8 - Sep 9
Total with taxes and fees
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A log cabin with a snow-covered roof, a front porch, and a garage.

5. 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, Exceptional, (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.
$455 nightly
The price is $493
Sep 10 - Sep 11
Total with taxes and fees
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
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, (120 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
Sep 8 - Sep 9
Total with taxes and fees
Charming Jackson Cottage w/ hot tub & woodstove!
A riverside cabin with a view of the river and surrounding trees.

7. Riverside Cottage • Fireplace • Mountain Views

Riverside Cottage • Fireplace • Mountain Views
Bartlett
$351 nightly
The price is $381
Sep 27 - Sep 28
Total with taxes and fees
Riverside Cottage • Fireplace • Mountain Views
A Story Land sign with a brick pathway leading to colorful buildings with distinct architectural styles.

8. Riverside Cottage • Private Beach • Mountain Views

Riverside Cottage • Private Beach • Mountain Views
Bartlett
$374 nightly
The price is $406
Sep 8 - Sep 9
Total with taxes and fees
Riverside Cottage • Private Beach • Mountain Views
A storefront with a blue awning and American flags, named "Paper Store Blacks Gift Shop."

9. 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, Exceptional, (20 reviews)
"This is a great place to stay with a dog"
United States
David M.
$192 nightly
The price is $208
Sep 22 - Sep 23
Total with taxes and fees
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
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, (4 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.
$199 nightly
The price is $216
Sep 22 - Sep 23
Total with taxes and fees
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 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
$183 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A two-story house with a white picket fence, a gravel driveway, and autumn foliage in the background.

12. 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
$261 nightly
The price is $283
Sep 8 - Sep 9
Total with taxes and fees
Cottage 1-2 - Pet Friendly $50 Fee-2 Bed / 1 Bath
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.
$276 nightly
The price is $299
Sep 8 - Sep 9
Total with taxes and fees
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.

14. 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, Exceptional, (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.
$268 nightly
The price is $291
Sep 8 - Sep 9
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Eastern Inn & Suites

Eastern Inn & Suites

10/10 Excellent
"A+++++ stay!! Staff was friendly and the manager was great! Rooms are super updated and spacious. Stayed in a 2 bedroom queen suite. Pool is a great size up to 6 feet. Free coffee and hot chocolate in the lobby. Outdoor fire pit, grill, lounge chairs, playground and basketball hoop. Plenty of parking and very spacious hotel. Bathrooms have a lot of room and updated. Showers have great pressure. 2 tv’s in the bedroom and living room area. Room featured updated temp control, microwave and fridge, sink that were all updated and a good size. Great facility!"
Brandon 2-night trip
Posted less than an hour ago
Eastern Inn & Suites

Find out more about Madison

Madison Cottages information

Number of reviews
2
Accommodation
192 Cottages
Lowest Price
$462
Highest Price
$462

Frequently asked questions

Why book your cottage in Madison with Expedia?
Expedia has some superb cottages in Madison, so get set for an unforgettable vacation on nature's doorstep. If you're on a budget, select how much you're willing to spend and the star rating of your property. Or, make use of our filters to search for cottages with a pool or a hot tub. We'll help you find the perfect place whatever your style of travel or plans.
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.

Explore a world of travel with Expedia