Bayfield harbor with moored sailboats and charming houses on hilly terrain, surrounded by lush greenery. Historic buildings dot the landscape, offering a picturesque view unique to Wisconsin's Lake Superior shoreline. | Houfy — Book Direct

Wisconsin vacation rentals

Vacation rentals in Wisconsin by owner — compare homes, condos and cabins, message verified hosts and book direct. See every charge before you pay.

Wisconsin invites you to explore the rocky shoreline of Door County, the water parks of Wisconsin Dells, the scenic Apostle Islands on Lake Superior, and bustling Milwaukee. The state is known for its summer festivals, cheese tastings, and the breathtaking landscapes of the Driftless Area. Houfy connects travelers directly with local hosts. Select from vacation homes on the shores of Lake Geneva, cabins in the Northwoods, or condos near Madison's State Street. Fall is an ideal time to visit for crisp air and beautiful fall foliage throughout the state.

Most popular destinations in Wisconsin

Where guests book most in Wisconsin — every one bookable direct with the host.

Top-Rated Vacation Homes in Wisconsin

Browse the highest rated vacation properties in Wisconsin.

Pinebrook Lodge

3 bd·1 ba
5· 110

$1,029.94 USD total for 3 nights

Oct 25 – 28, 2026

Beautiful, peaceful family getaway
We absolutely loved our stay at Pinebrook Lodge! The lakefront views from the house were beautiful, as were the wooded views from the rest of the windows. The pictures do not do it justice. We really liked how private this cabin's location is and how there was so much space to spread out both indoors and outside. Our son had a ball fishing from the dock and we all enjoyed paddling around the lake and playing in the sand. Every detail has been carefully, generously planned out from the fully stocked kitchen to the games and outdoor toys available for our use-- whenever we needed something, it was within reach as though we were in our own home. Everything was impeccably clean and the host was very informative and responsive. Truly, the most thoughtful vacation rental we have ever stayed in. What a delight!
Stay June 2023

Private Modern Cabin w/Hottub on 11 acres!

3 bd·2 ba
5· 44

$962.89 USD total for 3 nights

Oct 25 – 28, 2026

Hidden Pines Getaway
This is a terrific cabin nestled into an awesome setting that feels as though you're in the middle of the forest. The cabin itself has everything you need and more. You can sit outside around a really great firepit, you could hang out inside around the indoor fireplace, you could spend time in the basement shooting pool and watching movies, and you can roam through the abundance of tall trees and enjoy the wildlife. The additional bunkhouse is a nice touch if you're coming with a larger group. I wish we had the opportunity to have stayed longer because one day just wasn't enough. We grilled burgers, sat around the firepit, and had a great time. We look forward to returning. The hosts are very kind and are very prompt with messaging. Great experience overall!
B. M. · Stay October 2022

Unique Upper Barn Near Merrill WI and the WI River

1 bd·1 ba
5· 82

$690.20 USD $622.68 USD total for 3 nights

Oct 31 – Nov 3, 2026

The Barn was charming and we were thoroughly impressed by the details in and outside of the home. The location was absolutely stunning, offering beautiful views and a picturesque drive that set the tone for a relaxing getaway. The home itself was both cozy and spacious, featuring incredible details that clearly reflected a lot of love and care in its design. In the home they had lovely tea and great coffee options, loved the added perk. The surrounding town was cute, highly recommend the two Mexican restaurants (Los Mezcals & Casa- Amigos) in town and Auntie Ray's coffee shop. A special mention to the hosts, Laura and Bob, who were exceptionally kind and went above and beyond to assist us. They helped us with our tires before we left, which was greatly appreciated and gave us peace of mind for our 4-hour drive home. Overall, it was a fantastic experience that I would highly recommend to anyone looking for a serene retreat.
M. · Stay August 2024

Lake Cabin w/ King Bed & Fire Pit near Dells, Ski

3 bd·2 ba
5· 109

$784.10 USD total for 3 nights

Oct 26 – 29, 2026

My husband & I stayed @ Matt’s cabin with our adult children & 1 ½ year old granddaughter. The place is beautiful & our family loved it! The cabin is located on a quiet dead-end road. We relaxed on the deck a lot, but were thankful for the air conditioning since the temps hit the 90s. We cooked all of our meals @ the cabin (well stocked kitchen) using the gas stove, firepit & grill. (Matt provided an electric grill & we greatly appreciated that!) Our granddaughter enjoyed running around the backyard & we used the firepit most nights. We rented a pontoon from Johnson’s & were able to watch beautiful sunsets from the lake with the whole family. We caught quite a few nice sized fish! (Worms, minnows & firewood were purchased @ The Minnow Bucket). We enjoyed floating in the lake with our rafts & paddleboard. The candy shop in Montello was a fun visit! Matt was very quick to respond to any questions we had & we are very grateful he shared his lovely cabin with us! Many memories were made!
D. · Stay July 2023

Little Fork Lodge -Huge Firepit/Gameroom/Lakefront

4 bd·3 ba
5· 89

$1,934.19 USD total for 3 nights

Oct 24 – 27, 2026

Perfect Fishing Getaway
The property is amazing. The house is super clean and organized. The dock is wonderful. It has bumpers on 2 sides so we were able to dock a pontoon and fishing boat. The fire pit area is outstanding. I cannot say enough great things about the property. We had a group of 10, 35-40 year old males and we still felt like we had plenty of room. The bunk beds are not super small like you would expect. While most of the time was spent on the lakes, we enjoyed our time in the house playing different games which were provided by the hosts (Pandemic, chess, etc.). The fishing was wonderful, we caught mostly perch and pike. The only 2 downsides to the property are the abundance of mosquitos (it is the north woods, we expected this) and the steep hill down to the docks. I would caution anyone who is over 50 or not very mobile to think about this before booking. We certainly got a workout going up and down the hill. (Although we are not in the best shape ourselves...lol) I would highly recommend the property and the hosts are awesome. The only other reason I would tell someone not to book it, is because we want more days available for us to come back. Thank you so much for a wonderful vacation. Ryan and Friends
R. P. · Stay June 2023

Sprawling Cabin Estate with Hot Tub and Games

10 bd·6 ba
5· 60

$2,895.67 USD $2,777.53 USD total for 3 nights

Oct 24 – 27, 2026

Matt was an outstanding host. He answered my many questions quickly and was willing to do anything to please. The facility was better than the description. One can rarely find a place that can accommodate 18 people comfortably. Our group ranged in age from 1-71 and we all had our own spaces. There were “toys” for all of us to play with - books, kid toys, dvds, pool table, games, foosball, and on and on. 4 kitchen areas, with the main kitchen deluxe and able to handle 4 cooks at once. There were plenty of locations for eating, puzzlework or playing board games. What more can I say it was fabulous. We really appreciated having 2 living spaces - the smaller cabin was perfect for the family with small children who needed quiet space for nap times. We would definitely rent it again. Best family Christmas location!!!
S. · Stay January 2025

Butternut Bliss Cabin

2 bd·1½ ba
5· 71

$617.18 USD $571.28 USD total for 3 nights

Oct 24 – 27, 2026

Butternut Bliss is Blissful
My husband and I rented Butternut Bliss cabin for a last minute weekend getaway. We were looking for a place to relax and destress. The description and pictures don't do it justice. The weather outside was cold, snowy and blustery. inside was warm, comfy and cozy! The wood fireplace helped with the relaxing atmosphere. We enjoyed watching the deer on the lake that visited every morning and evening. We had one hiccup at check-in but Lisa was very prompt in contacting me and correcting the issue. We are hoping to return in maybe the summer or fall!
B. W. · Stay March 2022

$950.00 USD total for 3 nights

Oct 24 – 27, 2026

Unwinding by the river
My husband and I take two separate weekly trips every year. This trip to this lovely property was our last trip for the year. We enjoyed the house and it's beautiful view of the river. The current in the river was pretty swift due to the recent rains. We found everything in the house we needed to enjoy our stay. The area is in a small community, but there are some very nice choices for dining. We absolutely loved Ted's restaurant. It had a beautiful scenic lake view and very pleasant staff. My husband ordered the ribeye special. And when the steak arrived it reminded me of that movie with John Candy " The Great Outdoors " where John Candy took the challenge to eat the entire huge steak. My husband failed to eat it all... as it filled his entire plate. No t-shirt for him! The outdoor climate the week we were up was poor, or we would of spent more time outdoors enjoying the expansive level yard. Loved the attached porch. That was one of the big pluses when I decided to rent this property is the attached porch. The house is right off of a local county highway, but not many cars come by so it's not an issue at all. I would give this property a 5 Star rating. 5 being the best. It is perfect for a family gathering or a couples retreat as there is plenty of room for everyone to find there own place in the house. The property owners were very gracious and even sent me back some medication I accidentally left behind. Thank you for sharing your little piece of paradise. Sincerely, The Aronsons.
A. A.

Recommended Homes in Wisconsin

Handpicked properties we think you'll love in Wisconsin.

Eagle Ridge Hideaway Cabin

2 bd·1½ ba
4.95· 102

$1,287.02 USD total for 3 nights

Oct 24 – 27, 2026

Chippewa River Cabin

3 bd·1½ ba
4.89· 102

$674.04 USD total for 3 nights

Nov 1 – 4, 2026

Northwoods 3BR/2BA lakefront cabi on UTV/ATV trail

3 bd·2 ba
4.79· 58

$1,020.16 USD total for 3 nights

Oct 24 – 27, 2026

Family-Friendly Coveside Cottage

4 bd·2 ba
5· 7

$1,872.63 USD total for 3 nights

Oct 25 – 28, 2026

The Birch at Timberline Cottages - Door County

2 bd·1 ba
4.95· 174

$954.70 USD total for 3 nights

Nov 9 – 12, 2026

Peaceful Shores Door County

4 bd·2 ba
4.9· 144

$1,770.85 USD $1,623.64 USD total for 3 nights

Oct 25 – 28, 2026

Kozy Cabin at Johnson Lake-Family & Dog Friendly

2 bd·1 ba
4.93· 54

$2,043.30 USD total for 6 nights

Oct 30 – Nov 5, 2026

Lakefront house with jacuzzi

4 bd·2 ba
5· 16

$2,015.07 USD total for 3 nights

Oct 24 – 27, 2026

Pet friendly vacation rentals in Wisconsin

Bring your furry friend along! Browse pet-welcoming homes in Wisconsin.

Northwoods Nirvana! Eagle River @ Catfish Lake

3 bd·1 ba
4.92· 88

$2,305.30 USD total for 7 nights

Oct 26 – Nov 2, 2026

Lodge Life - Hayward WI Springbrook; Log Cabin

4 bd·2 ba
4.9· 41

$1,364.00 USD $1,255.10 USD total for 3 nights

Oct 24 – 27, 2026

Kozy Cabin at Witches Lake - Family & Dog Friendly

3 bd·2 ba
4.86· 37

$1,031.44 USD total for 3 nights

Oct 31 – Nov 3, 2026

Carter Cottage

4 bd·2 ba
5· 6

Soaring Pines Lakefront Cabin

3 bd·1 ba

$907.88 USD total for 3 nights

Oct 25 – 28, 2026

Long Lake Escape- Private lakefront cabin

2 bd·1 ba
4.87· 47

$893.74 USD total for 3 nights

Oct 24 – 27, 2026

Porch Time on Lil Sturgeon Bay

3 bd·2 ba
4.93· 68

$1,770.85 USD $1,623.64 USD total for 3 nights

Oct 25 – 28, 2026

Comfortable 3 BR Craftsman Bungalow (small dog OK)

3 bd·1 ba
4.74· 98

$880.71 USD total for 3 nights

Oct 24 – 27, 2026

Why visit Wisconsin

Discover what makes Wisconsin a perfect vacation rental destination.

Explore Door County

Charming coastal destination with outdoors.

Door County offers 300 miles of Lake Michigan shoreline with parks and quaint towns. Try Peninsula State Park for hiking, located about 1.5 hours from Green Bay.

Dive into Local History

Rich heritage with museums and historic sites.

Visit the Wisconsin Historical Museum in Madison to explore the state’s past. It's located right in downtown Madison.

Savor Wisconsin Cheese

Home to award-winning cheese varieties.

Head to the Wisconsin Cheese Mart in Milwaukee to taste over 150 varieties. It's a 10-minute walk from downtown.

Adventure in the Dells

Perfect for family fun and outdoor thrills.

Wisconsin Dells is renowned for its water parks and scenic river views, located about 55 miles from Madison.

Where to stay in Wisconsin

The best areas and neighborhoods for your vacation rental in Wisconsin.

Madison

Madison, the capital city, features the University of Wisconsin, lakes, and vibrant arts scenes.

Best for: students, families, art lovers

Milwaukee

Known for its breweries, the Milwaukee Art Museum, and lakefront festivals.

Best for: beer enthusiasts, urban explorers, culture seekers

Lake Geneva

A resort city with a picturesque lake, boutique shops, and outdoor activities.

Best for: romantic getaways, water sports, shopping

Door County

Offers charming small towns, wineries, and numerous state parks along the lake.

Best for: nature lovers, couples, wine enthusiasts

Find Wisconsin vacation rentals that suit your style

Vacation homes, cabins, cottages and more — pick the kind of Wisconsin vacation rental you want, then book it direct with the host.

Wisconsin vacation rentals with free WiFi, hot tub or air conditioning

Free WiFi, hot tub, air conditioning and more — every Wisconsin vacation rental here is listed by a verified host and bookable direct, with the price the host set.

Top attractions in Wisconsin

All within driving distance of Wisconsin vacation rentals.

Milwaukee Art Museum

Houses over 25,000 works of art, including a striking Santiago Calatrava-designed structure. · 0.5 miles from downtown Milwaukee

Wisconsin Dells Water Parks

Home to the world's largest concentration of indoor and outdoor water parks. · 55 miles from Madison

Devil's Lake State Park

Features magnificent 500-foot quartzite bluffs and beautiful hiking trails. · 40 miles from Madison

The House on the Rock

An eclectic architectural wonder showcasing unique collections. · 45 miles from Madison

Milwaukee County Zoo

Hosts over 2,100 animals from around the world in naturalistic habitats. · 10 miles from downtown Milwaukee

New Glarus Brewing Company

Famous for its Spotted Cow beer, offering brewery tours in a Swiss-themed town. · 27 miles from Madison

Best Time to Visit Wisconsin

The best time to visit Wisconsin for vacation rentals is June to September, when temperatures range from 73°F to 81°F and rainfall is moderate.

The best time to visit Wisconsin is November to February, when the weather is at its best. For lower prices and fewer crowds, November to March is the best time to book.

Best weatherNov – Feb
Best valueNov – Mar

OctNow

60°F16°C

Rainfall Moderate

Demand Mid

Nov

45°F7°C

Rainfall Low

Demand Low

Dec

33°F1°C

Rainfall Low

Demand Low

Jan

26°F-3°C

Rainfall Low

Demand Low

Feb

31°F-1°C

Rainfall Low

Demand Low

Mar

44°F7°C

Rainfall Moderate

Demand Low

Apr

55°F13°C

Rainfall Moderate

Demand Mid

May

68°F20°C

Rainfall Moderate

Demand Mid

Jun

78°F26°C

Rainfall Moderate

Demand Peak

Jul

81°F27°C

Rainfall Moderate

Demand Peak

Aug

79°F26°C

Rainfall Moderate

Demand Peak

Sep

73°F23°C

Rainfall Moderate

Demand Peak

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