Holiday rentals in Kendall

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Top-rated holiday rentals in Kendall

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Top guest favourite
A rustic cabin is surrounded by lush greenery, showcasing a spacious front porch with multiple wooden chairs and a swing. An outdoor fire pit is surrounded by seating, creating an inviting space for gatherings. A shaded gazebo adds to the outdoor comforts.
Cabin in Hill Point
4.97 out of 5 average rating, 631 reviews

Big R's Retreat Secluded and located in Nature

Welcome to our home: where we have found peace and relaxation for over 20 years. A German native, Big R fell in love with the open land and rolling hills of Wisconsin, becoming a US citizen in the 80s. He met Curly, a Chicago city girl, who brought a little city to his country life. They enjoy raising buffalo and spending warmer days on their porch enjoying the fresh air and beautiful views (with no mosquitos!). Now they want to share their idyllic and peaceful home with you. Drive down a dead-end road and pull up to a rustic cabin filled with high-tech and cozy amenities. We have something for everyone with a gas fireplace, tv (complete with dish, Cinemax, HBO and a Bluetooth sound system), board games and a full kitchen. Take a drink outside to soak in the hot tub or sit around the campfire. When the day is done, you will fall asleep instantly on the memory foam bed, either in the loft or the bedroom, and wake up to a beautiful sunrise looking out over your little getaway.

Top guest favourite
An A-frame home is featured, showcasing large glass windows that allow natural light to fill the interior. An outdoor deck is furnished with a cozy seating area and a fire pit. A hot tub is positioned nearby, surrounded by trees on the spacious property.
Home in Hancock
4.99 out of 5 average rating, 101 reviews

Luxury A-Frame | Sauna | Hot & Cold Tub | 7 acres

Welcome to Cedar Sands, our A-Frame resort style oasis 10 miles (13 min drive) to Sand Valley Golf Club on 7 acres of forest. Our year-round outdoor sauna, ice bath, hot tub, and firepit are the perfect amenities to create a wellness spa atmosphere after a long day on the course, trails, or lake. The property nestles up to a trout stream you can fish at the back of the lot. Inside, enjoy our hardwood floors, electric fireplace, coffee bar, and more to make your time away as relaxing as possible.

Guest favourite
A rustic log cabin is framed by green trees, featuring a steeply pitched roof and decorative wood accents. A welcoming front porch leads to a door with a unique design, while a large window showcases flowing red curtains, blending natural elements with cabin charm.
Cabin in Ontario
4.91 out of 5 average rating, 138 reviews

Country Living Cabin

Brush Creek Log Cabins is your perfect get away for couples or the whole family. If you are looking to relax, do some recreational activities like canoeing , bike riding, hiking, antiquing and Amish shopping or spend time with that special someone you can find it just a few hours from home. We are in between Ontario and Cashton, off of Hwy 33. Over looking the Amish farms below. There are fairs and festivals many with tractor pulls nearby. Warrens cranberry festival and the Dells are nearby.

Top guest favourite
A durable fabric shelter is set amidst lush greenery, featuring an inviting porch with outdoor seating. Flower boxes are trimmed with vibrant blooms, and a picnic table is positioned nearby. The structure is designed for comfort, blending seamlessly with the natural surroundings.
Campsite in Kendall
4.9 out of 5 average rating, 166 reviews

Driftless Bluff Glamping Cabin, Peaceful, Secluded

Rustic forest glamping in a heavy duty waterproof fabric shelter, 14 x 20ft. with a 5ft. awning. The perfect get away from it all, relax and enjoy nature. Flashlights, solar lights, propane 2-burner stove, and fire pit with grate. Kitchen set up with cooler, dishes, silverware, fully stocked coffee bar, filter water pitcher, shower bucket and most everything else. Compost toilet and foot pump sink. Small wood stove for when it's cold and a fan for when it's hot with battery to charge extras.

Guest favourite
A spacious deck is surrounded by lush greenery, featuring a wooden table with colorful chairs. A comfortable bench adds seating, while a gas grill is positioned nearby, creating an inviting outdoor space perfect for relaxation and dining.
Cabin in Forest
4.97 out of 5 average rating, 201 reviews

Driftless Trout Cabin - Hillsboro, Wisconsin

Welcome to our spring-fed cordwood log cabin on 5.66 acres in Wisconsin’s beautiful Driftless region. Enjoy: - World class trout fishing for native brookies or abundant browns - Hiking nearby at the breathtaking Wildcat Mountain State Park or the 8,569 acre Kickapoo Valley Reserve - Canoeing or kayaking the beautiful Kickapoo River - Biking renowned bikes trails through the countryside - Sipping Wonderstate Coffee or Driftless Glen Bourbon on the deck while listening to the babbling spring

Top guest favourite
A rustic cabin exterior is depicted with wooden accents and a stone chimney. The porch features steps leading to a scenic view of the Mississippi River and rolling hills, framed by trees under a clear blue sky.
Cabin in Ferryville
4.99 out of 5 average rating, 106 reviews

Eagle View Lodge - 1850's Log Cabin w/ Hot Tub

In the heart of the Driftless, atop the Mississippi , enjoy the tranquility of a centuries-old Appalachian cabin. Relax on the deck & take in dramatic sunsets, soaring eagles & glistening stars. Soak in the hot tub & gaze at the majestic Mississippi. Host unforgettable dinners in the screened deck & share stories by the fireplace. Only 30 mins from Viroqua & Prairie du Chien, experience the natural beauty of the driftless region - hiking, fishing, hunting, biking - whatever inspires you.

Top guest favourite
A spacious grassy area is shown, featuring several sheep grazing peacefully. A large tree provides shade near the cabin, which features a green metal roof and a screened-in porch. A rustic swing is visible beneath the tree, enhancing the serene environment.
Tiny home in Ontario
4.91 out of 5 average rating, 151 reviews

Maggie's Place at Echo Valley Farm

Enjoy simple living in this cabin set in the heart of our farm. Walk the property or go the short distance to Wildcat Mountain State Park or to Kickapoo Valley Reserve. A hiker's paradise you can also enjoy fresh baked goods from our bakery May through October, or pre order year round. Linens on 2 comfortable beds, bottled water and wash water, coffee maker, electric kettle, fire pit, charcoal grill and a non chemical port-o-let. No frig. No pets. LGBTQ owned and operated. BIPOC welcome.

Top guest favourite
The exterior of Hidden Hollow House features a two-story white farmhouse surrounded by lush greenery and colorful flowerbeds. A wooden sign reading 'Hidden Hollow' is positioned prominently at the front. A small deck with seating invites relaxation amidst the peaceful surroundings.
Home in Hillsboro
4.92 out of 5 average rating, 123 reviews

Driftless Area Hidden Hollow House

We are excited to offer you the opportunity to visit Hidden Hollow House! Secluded among the rolling hills and rock outcroppings of the Driftless Area it offers the peace and quiet you have been looking for yet centrally located between small towns and outdoor recreational areas. Come and enjoy a restful and quiet stay while exploring the beautiful and friendly Driftless Area. You will have a sense of peace knowing you have found a place to return to and re-energize whenever you need it!

Top guest favourite
An outdoor deck features a cedar hot tub and seating area, surrounded by natural landscapes. In the background, a fire pit is set up with chairs, while a picturesque sunset casts a warm glow over the serene surroundings.
Cabin in Viola
4.99 out of 5 average rating, 181 reviews

Secluded cabin,cedar sauna & hot tub,outdoorshower

360 views in the middle of 75 organic acres, no neighbors in site. Outdoor Cedar hot tub & infrared sauna, heated outdoor shower, two king loft bedrooms, full kitchen, back deck with custom hibachi grill to watch sunrise and front covered deck to watch sunset. Indoor/ outdoor fire places. Wildflower fields.We try to give our couples priority booking when they rent our wedding venue 2 miles down the hill (Chapters on the Horizon) that is why we do not instant book.

Top guest favourite
The exterior of the home features a light green facade with a metal roof. A welcoming porch is visible, furnished with white rocking chairs. Lush grass surrounds the house, and a large tree can be seen beside it, contributing to a peaceful countryside setting.
Home in Union Center
4.99 out of 5 average rating, 147 reviews

Charming country home - great vacation area.

This attractive, peaceful country home is nearby to many family tourist attractions: including Wisconsin Dells, Lake Redstone Park, Elroy-Sparta Bike Trail, fishing, hiking, and canoeing. Provisions for a simple country breakfast are included in your stay. This newly remodeled home with a 2 story layout provides plenty of room for up to 7 guests. Large backyard includes a firepit, as well as a view of the adjacent golf course. Large driveway to park in.

Top guest favourite
A two-story house features a white exterior with green trim, including a covered front porch with seating. A balcony is visible on the second floor above the porch. Lush green grass surrounds the home, with trees providing shade in the background.
Home in Wilton
4.98 out of 5 average rating, 196 reviews

Cozy Three Bedroom House

Relax while you enjoy slow living in the peaceful town of Wilton. There are plenty of activities and places to see nearby if you’d like to get out and enjoy the small town atmosphere. Sparta Elroy Bike Trail (Just down the road) Wildcat Mountain (11 Miles) Wisconsin Dells (60 Miles) Canoeing/Tubing/Kayaking on the Kickapoo (8 Miles) Things to Do/Check Out: Friday Night Fish Frys Tractor Pulls Cheese Stores/Creamerys Horseback Riding Fishing

Top guest favourite
A path lined with glowing string lights leads to a charming lodge nestled among trees. The structure features large windows and a welcoming entrance, surrounded by natural landscaping and gravel. Two outdoor chairs are positioned for relaxation amidst the serene woodland setting.
Tiny home in Elroy
4.99 out of 5 average rating, 134 reviews

Opal Little Lodge - Panoramic Tree Top View

Check out Emerald Little Lodge also! Opal is nestled into the trees overlooking a peaceful woodland valley and giving the illusion of being in a tree house. Designed and built by Wisconsin Tiny Homes, Opal showcases a light and airy blend of modern and traditional design and is thoughtfully and luxuriously appointed. Immerse yourself in nature and enjoy a restful getaway alone or with a companion! Dedicated 500Mbps fiber optic WiFi.

Popular amenities for Kendall holiday rentals