Holiday rentals in Greenleaf

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Top-rated holiday rentals in Greenleaf

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Top guest favourite
Home in Cleveland
5 out of 5 average rating, 11 reviews

Shoreline Serenity

Welcome to ''Shoreline Serenity''! 200 ft of Lake Michigan frontage w/unobstructed views that go on for miles and tucked away on a 2-acre lot offering peace & privacy. Inside the home, you will be drawn to the beautiful views through the full wall of east facing windows & patio doors. The interior is cozy, clean, and comfortable. Fully equipped kitchen w/coffee bar. Main level has (2) bedrooms including the primary bedroom w/fantastic views. The spacious upper level loft has a king & twin bed.

ValueLocationBeach

Top guest favourite
A serene view of the water at dusk is framed by trees along the riverbank. The calm surface reflects soft colors of the sunset, enhancing the tranquil natural setting.
Home in Appleton
4.96 out of 5 average rating, 127 reviews

Riverfront log cabin in the heart of the valley

◖30 minutes to Oshkosh(EAA) & Green Bay(Lambeau), 10 minutes to Downtown Appleton ◖10 minutes to Kimberly boat launch; travel the Fox River Locks system You will LOVE this property: ◖Outstanding views from the amazing sunsets to the relaxing water & wildlife ◖Newly renovated with many amenities ◖Enjoy the Northwoods setting in the heart of the valley ◖Relax at end of the day sitting around a campfire or by indoor fireplace ◖Tie your boat to dock in front of property ◖Full kitchen/outdoor grill

ValueFamilyIndoor spaces

Superhost
A modern living room features a spacious seating area with a cozy sectional sofa and a stylish accent chair. A TV is mounted on the wall, surrounded by decorative elements. Natural light filters through large windows, highlighting the warm wooden accents and sleek furnishings.
Home in Green Bay
4.92 out of 5 average rating, 190 reviews

Centrally Located, Updated Home

Step in to your cozy, sun-drenched haven, reminiscent of your favorite corner café. Thoughtfully crafted to blend functionality, comfort, and style, this space is sure to become your cherished home away from home. Situated just minutes from Downtown Green Bay, major highways, and family-friendly attractions, this modern retreat caters to both casual and business travelers. Experience a genuine sense of belonging with a stay designed to foster connection, creativity, consciousness, and community!

ValueFamilyBeach

Guest favourite
The charming cabin features a rustic log exterior with a green roof and white trimmed windows. A small porch with two chairs invites relaxation. A private outdoor restroom is positioned nearby, ensuring convenience while maintaining privacy in the serene woodland setting.
Cabin in Greenleaf
4.81 out of 5 average rating, 53 reviews

Little Rustic Cabin in the Vineyard Glamp Site

Experience a one-of-a-kind stay in a romantic vineyard cabin just 30 miles from Green Bay. Nestled among the vines, enjoy glamping comforts—queen bed, fridge, microwave, coffee maker, grill, fire pit, and private outdoor restroom. Stroll one of Wisconsin’s oldest vineyards, sip handcrafted wine, and stargaze in peaceful seclusion. Perfect for couples seeking a cozy, nature-filled escape close to the city yet far from the noise, where every sunset feels magical and every night inspires the soul

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Top guest favourite
Cabin in Algoma
4.98 out of 5 average rating, 126 reviews

Door County Cabin on Lake Michigan | No clean fee!

Welcome to our cabin on Lake Michigan. Our cabin sits near the end of a dead end road and is very peaceful and quiet. At the end of the road is a historic county park. The cabin sleeps up to 8 guests and has all the amenities of home! Relax on the deck, take the kayaks for a spin, enjoy a fire indoors or out, or ride our bikes. Play games late into the night. Shoot hoops! Or, take in amazing sunrises. We offer a pet-free space. Google “Low Cabin” for our website and social media pages!

FamilyLocationWifi

Top guest favourite
The exterior of a cabin is depicted, featuring large windows framed by wood. Warm light emanates from within, revealing a cozy interior with a lamp and seating. Snow covers the ground, and icicles hang from the roof, creating a serene winter scene.
Cabin in New London
4.99 out of 5 average rating, 135 reviews

Secluded Cabin with Sauna

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

FamilyLocationAmenities

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 274 reviews

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

LocationValueHiking

Top guest favourite
A scenic view of the property showcases a spacious driveway leading to a well-maintained guest house and main residence, framed by mature trees. Lush green grass surrounds the area, enhancing the country setting. The distant fields are visible in the backdrop.
Guest house in Kaukauna
4.97 out of 5 average rating, 97 reviews

Country Sky Private Guest House (3 bedroom 1 Bath)

Welcome to our private guest suite on country acres! We welcome guests in our 1,050 sq foot 3 bedroom 1 bath guest house. The suite is a private separate building on our property. We are 11 minutes from Green Bay/Lambeau Field, 20 minutes from Appleton/Fox Cities, and 50 miles (1 hr 10min) from Oshkosh/EAA Venture We enjoy the country space and privacy with easy/quick access to urbanized cities around us for all the necessities. We love animals, but we are a pet-free rental.

LocationFamilyParking

Top guest favourite
Guest house in Oshkosh
4.96 out of 5 average rating, 202 reviews

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

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Top guest favourite
Home in Kaukauna
4.99 out of 5 average rating, 109 reviews

Modern Comfort & Charm with Historic Flair

Ann's Queen Anne is a historic 2-story home with an updated interior offering comfort, convenience, and style. New furnishings and luxurious features make this an ideal place for a retreat, or a base of operations for exploring the area or attending a Packers game at Lambeau Field. Attention to detail and personal touches will make your stay a unique and special experience. Close to Appleton, Oshkosh, Green Bay, Door County, Manitowoc & Sheboygan/Kohler.

FamilyLocationWifi

Top guest favourite
The modern lake house is framed by tall trees and features expansive floor-to-ceiling windows, providing views of the interior. Soft outdoor lighting subtly highlights the sleek architecture, while the lush green lawn invites a serene evening atmosphere.
Home in Clay Banks
4.98 out of 5 average rating, 121 reviews

Door County Lake House 50 min from Lambeau Field

We are excited to introduce our Architect-designed modern lake house in the town of Clay Banks! Enjoy serenity, sweeping views of Lake Michigan from a secluded back deck & expansive windows from every room in the house. Embrace slower living, waterfront amenities, neighborhood park with trails and the magic of lake life. You’ll enjoy water fun for the whole family, huge back deck with dining for 8, an outdoor lounge area, and fire pit near the water.

ValueFamilyGetting around

Guest favourite
Home in Greenleaf
4.88 out of 5 average rating, 24 reviews

Wine Country Farmhouse | Golf + Wineries

Wisconsin wine country is your backyard. Vineyard View is a beautifully updated 1900s farmhouse in the heart of Greenleaf — home to some of Northeast Wisconsin's best wineries and golf courses, all within minutes of your front door. Whether your crew is here to sip through a local wine trail, squeeze in 18 holes, or simply unwind around a fire pit under wide-open country skies, this is your home base. Located just minutes from De Pere and Green Bay.

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Popular amenities for Greenleaf holiday rentals