Madison Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Madison, Wisconsin, USA

Beautifully updated home close to downtown New Glarus
10.0 (66 Reviews)
2 Bedrooms 8 Guests
The Buckingham Inn
FromCA $177 per night
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10.0 (6 Reviews)
3 Bedrooms 6 Guests
The Buckingham Inn
FromCA $279 per night
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9.8 (44 Reviews)
1 Bedroom 2 Guests
‘Happy’s Haven’ Cabin w/Gas Grill & Fire Pit!
10.0 (63 Reviews)
2 Bedrooms 6 Guests
Waterfront Lodi Vacation Rental on Lake Wisconsin!
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10.0 (3 Reviews)
3 Bedrooms 8 Guests
The Speckled Hen Inn B&B
FromCA $383 per night
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9.8 (9 Reviews)
1 Bedroom 2 Guests
Beautiful New Glarus, WI Apartment
FromCA $216 per night
10.0 (59 Reviews)
1 Bedroom 2 Guests
Luxury Prairie Retreat 5 Min from Madison!
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10.0 (1 Review)
3 Bedrooms 10 Guests
Mendota Lake House Inn
FromCA $196 per night
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8.8 (360 Reviews)
1 Bedroom 2 Guests
Adorable Updated Cozy Cottage set on Lake Wisconsin's Sunset Bay
10.0 (40 Reviews)
2 Bedrooms 6 Guests
Happys Haven Cabin with Gas Grill and Fire Pit!
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10.0 (1 Review)
2 Bedrooms 6 Guests
Sugar River Suite - Your Sweet Escape in the Heart of it All!
10.0 (20 Reviews)
2 Bedrooms 5 Guests
Cannery Square Apartment 104
FromCA $416 per night
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9.5 (2 Reviews)
2 Bedrooms 5 Guests
Charming Lake Ripley Cottage with Water View!
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9.5 (2 Reviews)
2 Bedrooms 5 Guests
Lake WI Rental: Private Pier: Sunsets
New
2 Bedrooms 4 Guests
Spacious Lakehouse with Deck, Kayaks, and Dock!
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9.0 (1 Review)
4 Bedrooms 12 Guests
Liberty Valley Short Term Rental - 27
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9.0 (1 Review)
1 Bedroom 2 Guests
A Home Away from Home in the Quaint Village of New Glarus
10.0 (343 Reviews)
4 Bedrooms 12 Guests
Econo Lodge Madison East
FromCA $82 per night
7.1 (422 Reviews)
83 Bedrooms 20 Guests
Main Street Sun Prairie WI - 2 Bedroom
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7.0 (1 Review)
2 Bedrooms 5 Guests
HOLY COW! Guest Haus in The Heart of New Glarus
10.0 (81 Reviews)
3 Bedrooms 6 Guests
Family-Friendly Lake Waubesa Home Boat and Swim!
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New
3 Bedrooms 6 Guests
Okee Bay House on Lake Wisconsin w/Private Dock!
10.0 (22 Reviews)
4 Bedrooms 8 Guests
Lakefront and Dock! Family-Friendly Wisconsin Escape
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New
1 Bedroom 12 Guests
Lake Wisconsin Family Home with great views, beach access, pier.
10.0 (18 Reviews)
3 Bedrooms 6 Guests
Fire Pits, Views and Yard Luxe Mt Horeb Getaway!
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New
5 Bedrooms 12 Guests
Modern cabin with pool and hot tub and outdoor sauna! Wanderlust Cabin!
10.0 (16 Reviews)
4 Bedrooms 8 Guests
Outdoor Oasis Luxe Flat in Mt Horeb!
FromCA $1,075 per night
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New
3 Bedrooms 8 Guests
Brigham View
FromCA $356 per night
10.0 (15 Reviews)
4 Bedrooms 11 Guests
Spacious and Secluded Madison Home Near Dtwn!
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New
5 Bedrooms 8 Guests
Hike, Ski, Ice Fish & Explore: Lodi Lake Escape!
10.0 (9 Reviews)
3 Bedrooms 6 Guests
Lake Wisconsin Retreat with Dock Great for Groups!
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New
5 Bedrooms 8 Guests
Beaver Dam Lake Retreat with Fire Pit and Dock!
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New
4 Bedrooms 14 Guests
Lake Wisconsin Retreat w/Dock: Great for Groups!
10.0 (2 Reviews)
5 Bedrooms 8 Guests
Okee Bay House on Lake Wisconsin with Private Dock!
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New
4 Bedrooms 8 Guests
Lake Wisconsin - Sunset Bay Stunner
FromCA $1,125 per night
9.8 (23 Reviews)
4 Bedrooms 10 Guests
4 BR Tranquil Lakefront Retreat w/Fire Pit
9.8 (21 Reviews)
4 Bedrooms 12 Guests
Spacious, Pet Friendly Apartment in the Heart of Downtown
9.8 (17 Reviews)
3 Bedrooms 6 Guests
Waterfront Lodi Vacation Rental on Lake Wisconsin!
9.6 (22 Reviews)
3 Bedrooms 8 Guests
Madison Arboretum Mid-Century Ranch Screen Porch, Fireplace
10.0 (27 Reviews)
3 Bedrooms 6 Guests
Hike, Ski, Ice Fish and Explore Lodi Lake Escape!
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New
3 Bedrooms 6 Guests
Spacious & Secluded Madison Home Near Dtwn!
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New
1 Bedroom 2 Guests
Renovated 4 BR Home Near Madison
FromCA $526 per night
10.0 (26 Reviews)
4 Bedrooms 10 Guests
Cannery Square Unit - 106 by Patriot Properties
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New
1 Bedroom 5 Guests
Holiday Inn Express & Suites Madison Central by IHG
9.8 (986 Reviews)
1 Bedroom 2 Guests
SpringHill Suites by Marriott Madison
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9.8 (690 Reviews)
1 Bedroom 2 Guests
Beautiful Lake Monona Home-Minutes to Downtown Madison
10.0 (23 Reviews)
5 Bedrooms 12 Guests
Cannery Square Short Term Rentals -102
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New
1 Bedroom 2 Guests
Updated 3 bed + office ranch home close to Downtown Madison
10.0 (21 Reviews)
4 Bedrooms 8 Guests
Cannery Square Short Term Rentals -104
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New
2 Bedrooms 5 Guests
Cozy Winter Haven | Minutes to Downtown
10.0 (20 Reviews)
3 Bedrooms 7 Guests
Driftless Edge Farm
FromCA $177 per night
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New
1 Bedroom 4 Guests
Beautifully Updated Lake House
New
1 Bedroom 14 Guests
Family-Friendly Lake Waubesa Home: Boat + Swim!
10.0 (20 Reviews)
3 Bedrooms 6 Guests
Beautifully Updated Lake House
New
1 Bedroom 14 Guests
Cheerful 3-bedroom cottage 2 blocks from the lake
10.0 (20 Reviews)
3 Bedrooms 8 Guests
Lake House-Stoughton
FromCA $577 per night
New
2 Bedrooms 6 Guests
Rock River Access! Peaceful Horicon Studio
New
1 Bedroom 2 Guests
Centrally located 4 Bedroom beautiful home.
10.0 (17 Reviews)
4 Bedrooms 8 Guests
Par-fect Escape on Lake Windsor Golf Course
New
1 Bedroom 10 Guests

About Madison Vacation Rentals

With more than 732 Madison vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Madison.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Madison, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Madison. Places to stay near Madison are 663.05 ft² on average, with prices averaging CA $417 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Madison with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Madison?

What are the top vacation rentals in Madison?

How many Rentbyowner vacation rentals are available in Madison?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 732 in the Madison area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Madison. 

Nearby Neighborhood (14)

NeighborhoodProperty Count
Marquette Vacation Rentals in Madison, Wisconsin 168
Regent Vacation Rentals in Madison, Wisconsin 144
Tenney-Lapham Vacation Rentals in Madison, Wisconsin 159
Spring Harbor Vacation Rentals in Madison, Wisconsin 107
Bay Creek Vacation Rentals in Madison, Wisconsin 164
Shorewood Hills Vacation Rentals in Madison, Wisconsin 91
Greenbush Vacation Rentals in Madison, Wisconsin 148
North Lake Mendota Vacation Rentals in Madison, Wisconsin 248
Emerson East Vacation Rentals in Madison, Wisconsin 131
Eagle Heights Assembly Vacation Rentals in Madison, Wisconsin 93
Lakeview Vacation Rentals in Madison, Wisconsin 79
Middleton Springs Vacation Rentals in Madison, Wisconsin 65
Meadowood Vacation Rentals in Madison, Wisconsin 56
Waubesa Beach Vacation Rentals in Madison, Wisconsin 33