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Madison Vacation Rentals

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Check prices for these dates

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

Our top choices for Madison vacation rentals

A modern building with a black exterior and a large glass entrance.

1. Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.4 out of 10, Exceptional, (9 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
$133 nightly
The price is $144
Oct 12 - Oct 13
Total with taxes and fees
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A modern building with a black exterior, a wooden-framed entrance, and a stone staircase leading up to a glass door.

2. Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Mila was always available when I needed anything. Very flexible and the place was nice."
United States
Donna B.
$148 nightly
The price is $162
Oct 16 - Oct 17
Total with taxes and fees
Spacious modern living in a quite neighborhood
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

3. Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Madison
10.0 out of 10, Exceptional, (45 reviews)
"Great experience"
United States
Chase D.
$321 nightly
The price is $350
Oct 12 - Oct 13
Total with taxes and fees
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A laundry room with a washing machine, dryer, and vacuum cleaner.

4. Dog Friendly, Steps to Lake, Golf, & Theate

Dog Friendly, Steps to Lake, Golf, & Theate
Madison
10.0 out of 10, Exceptional, (1 review)
"The house is really nice convenient local area. We would stay there again when we come into town."
United States
Al Q.
$443 nightly
The price is $483
Nov 2 - Nov 3
Total with taxes and fees
Dog Friendly, Steps to Lake, Golf, & Theate
A wooden kitchen with a large window, a black countertop, and three bar stools.

5. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (4 reviews)
"Great for kids. Lots of space. Convenient location. Plenty to do locally or venture out to explore. Recommend renting the golf cart to get back and forth down the camp road to the dock.. water is clear and clean, rock bottom at shore. Fast response from host who lives close by."
United States
Melissa B.
$657 nightly
The price is $716
Oct 12 - Oct 13
Total with taxes and fees
Welcome to "the east Madison chapel"
A cozy cabin interior with a wooden ceiling, a sofa, a patterned armchair, a table with a coffee cup, and large windows with curtains.

6. Sugarloaf Ski Basecamp Riverfront Cabin + Fire Pit

Sugarloaf Ski Basecamp Riverfront Cabin + Fire Pit
3.0 star property
North Anson
$287 nightly
The price is $313
Oct 12 - Oct 13
Total with taxes and fees
Sugarloaf Ski Basecamp Riverfront Cabin + Fire Pit
A cabin with a deck, a covered outdoor seating area, and a small porch.

7. Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!

Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
Strong
9.4 out of 10, Exceptional, (150 reviews)
"We really enjoyed our stay here! The host was very nice and welcoming. The lake access was easy for boating and swimming. Wished that the place was cleaner when first arrived, but overall would highly recommend this place!"
United States
Justine M.
$139 nightly
The price is $151
Oct 12 - Oct 13
Total with taxes and fees
Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

8. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, Exceptional, (4 reviews)
"A lovely spot. It is extremely clean. The hostess has thought of everything! There are plenty of nice towels and facecloths and bedding. The bed is very comfortable. We have enjoyed our stay"
Canada
Sherrie
$150 nightly
The price is $164
Oct 16 - Oct 17
Total with taxes and fees
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A cabin with a stone foundation, wooden exterior, and a covered porch.

9. Sugarloaf Ski Basecamp Riverfront Cabin + Fire Pit

Sugarloaf Ski Basecamp Riverfront Cabin + Fire Pit
Embden
$280 nightly
The price is $305
Oct 12 - Oct 13
Total with taxes and fees
Sugarloaf Ski Basecamp Riverfront Cabin + Fire Pit
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

10. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 reviews)
"The cabin was perfect for our two night stay. It was very clean and it felt just like being at home. Misty was a responsive host and I would definitely rent here again."
United States
Tonilynne D.
$158 nightly
The price is $172
Oct 22 - Oct 23
Total with taxes and fees
Charming cabin in the birches right on the atv trail!
A modern living room with a beige sofa, a dining area with a wooden table and chairs, a kitchen with white cabinets, and a mounted TV on the wall.

11. Charming renovated Bank building direct access for ATV/ snowmobiles

Charming renovated Bank building direct access for ATV/ snowmobiles
Bingham
9.2 out of 10, Wonderful, (26 reviews)
"Very wonderful charming place to stay in the western mountains!"
United States
Eric S.
$155 nightly
The price is $169
Oct 12 - Oct 13
Total with taxes and fees
Charming renovated Bank building direct access for ATV/ snowmobiles
A signboard with trail information for the Great Carrying Place Portage Trail.

12. Rural Maine cabin near Flagstaff Lake, Bigelow Preserve and Sugarloaf

Rural Maine cabin near Flagstaff Lake, Bigelow Preserve and Sugarloaf
Highland Plantation
10.0 out of 10, Exceptional, (121 reviews)
"This was such a great stay for a friend and I who were visiting sugarloaf over the weekend. Highly recommend, the absolute sweetest hosts. Thank you for having us, will stay again!"
United States
Ryan Y.
$178 nightly
The price is $194
Oct 12 - Oct 13
Total with taxes and fees
Rural Maine cabin near Flagstaff Lake, Bigelow Preserve and Sugarloaf
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

13. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (20 reviews)
"Great communication. The location was excellent for a few day trips. Very clean and well maintained. Would definitely stay here again if in the area."
United States
Patricia
$214 nightly
The price is $233
Oct 12 - Oct 13
Total with taxes and fees
Discover Oakland charm near Colby College 10 min
A wooden cabin with a porch, a door, and a green chair.

14. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
$216 nightly
The price is $235
Nov 3 - Nov 4
Total with taxes and fees
Sister A-Frame in Woods B
A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

15. Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Smithfield
8.0 out of 10, Very good, (1 review)
"Very clean and centrally located for the Belgrade Lakes. Nice people and I will definitely stay again."
United States
Mike F.
$150 nightly
The price is $164
Oct 31 - Nov 1
Total with taxes and fees
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

16. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
$215 nightly
The price is $234
Oct 12 - Oct 13
Total with taxes and fees
The heart of the Belgrade Lakes
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

17. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (64 reviews)
"Less than 5 minutes to Colby. We were there for a camp. AC in both bedrooms. Nice artwork and decor."
United States
Leslie G.
$233 nightly
The price is $254
Nov 2 - Nov 3
Total with taxes and fees
Cozy House in the heart of Waterville Maine.
A dense forest with tall trees and lush green ferns.

18. Minimal & Cozy Victorian Private Room in Downtown Skowhegan

Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Skowhegan
$313 nightly
The price is $341
Oct 18 - Oct 19
Total with taxes and fees
Minimal & Cozy Victorian Private Room in Downtown Skowhegan
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

19. A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.
New Sharon
10.0 out of 10, Exceptional, (30 reviews)
"Loved the cabin and the view!! Had a great stay, thank you to our host!! Would love to stay again "
United States
Matt W.
$376 nightly
The price is $409
Oct 13 - Oct 14
Total with taxes and fees
A soul soothing escape. Artistically built and lovingly maintained.
Room

20. Moose Cabin

Moose Cabin
Pleasant Ridge Plantation
$134 nightly
The price is $146
Oct 12 - Oct 13
Total with taxes and fees
Moose Cabin
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Its older but well maintained. The rooms with the Fireplaces are mostly upstairs, but you pick up a vaulted ceiling as well. The room was huge, actually has something of a living room. There is a washer and dryer onsite which was helpful in my situation. Theres a couple of Restaurants within walking distance and a Walmart is about 1/10 of a mile way."
ROBERT L. 2-night trip
Posted 8 hours ago
Fireside Inn & Suites Waterville

Find out more about Madison

Everything you need to know about Madison vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Madison in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $151 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Madison rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Madison?

Yes, we have vacation rentals near the most popular sights in Madison, or you can go with a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental that Madison has to offer?

Welcome to "the east Madison chapel": This highly rated vacation home rental in Madison offers a patio and WiFi to help you feel comfortable in your new surroundings.

How many vacation rentals will I find in Madison?

With 10 Expedia vacation rentals, you're sure to find just the right place for your Madison stay.

What’s there to see and do in Madison?

While you're exploring the area, Kennebec River and Embden Pond are a couple of picturesque spots to get outside and enjoy nature. Skowhegan State Fairgrounds and University of Maine - Farmington are a couple of places you'll find in the larger area.

What’s a vacation rental in Madison like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Madison. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.