Family-friendly holiday rentals in Baraboo

4.96 out of 5 average rating, 95 reviews

A modern cabin exterior features a striking combination of black and natural wood finishes. Large glass panels illuminate the interior, reflecting warm light. A covered patio with seating options and a stylish hanging chair is set against a backdrop of surrounding trees.

Cabin in Wisconsin Dells

Black sheep cabin with barrel sauna. New build!

Discover peace and style in this brand-new cabin tucked away in the woods—just minutes from the Dells. Modern aesthetic and thoughtful details, this secluded retreat blends natural beauty with upscale comfort. Wake up to birdsong, sip coffee on the private patio, and unwind in a space that feels serene & sophisticated. Whether you're seeking a romantic getaway, a quiet workcation, or a base for Dells adventures, this peaceful woodland hideaway offers the perfect balance of privacy and proximity

A quaint gray house features a dark front door framed by two windows with flower boxes. A stone path leads to the entrance, surrounded by lush green grass and shrubs. The home's simple design is complemented by a picturesque backdrop of leafy trees.

4.96 out of 5 average rating, 151 reviews

Cottage Near Devil's Lake

Perfect Location! Under ten minutes to almost everything. Our cozy and romantic getaway is nestled in the scenic Baraboo Bluffs, just minutes to Devil's Lake, Devil's Head Resort, Historic Downtown Baraboo, wineries, distilleries & more. Take the picnic set to Devil's Lake or Parfrey's Glen, then relax on the patio for smores and yard games around the fire pit. Finish the evening snuggled up with wine & vinyl on the player. We have ample parking so bring the boat, we'd love to help you getaway.

The house is illuminated at night, revealing a spacious deck adorned with soft lighting. Large windows display a welcoming interior ambiance. The surrounding garden features lush greenery and blooming flowers, while the towering trees create a serene backdrop.

5 out of 5 average rating, 159 reviews

Crown Lodge, Baraboo Bluffs

Nestled deep in the Baraboo Bluffs on a dead-end country road. A true cabin-in-the-woods feel without sacrificing space or amenities. Perfect for family getaways, outdoor enthusiasts, or anyone craving a peaceful recharge. Whether you’re sipping coffee or drinks on the deck while watching wildlife, hiking the bluffs, skiing nearby or visiting the Dells, there’s no shortage of things to do, or not do! Minutes from Devil’s Lake, Devil’s Head Resort, Ice Age Trails & 25 minutes to Wisconsin Dells

4.95 out of 5 average rating, 121 reviews

The open living area features high ceilings and large windows that allow natural light to fill the space. A green sectional sofa and matching ottoman are arranged around a coffee table. A wooden dining table is visible in the background, along with a modern kitchen.

Cabin in Portage

Secluded WI River Getaway w/ Hot Tub near Golfing

Get away from daily routines & refresh by the Wisconsin River at your private & peaceful retreat located near Devil's Lake, Cascade Ski & Devil's Head Ski/Golf Resorts & WI Dells. Perfect for families w/ 9 beds, 8 person Hot Tub, 6 Kayaks (May-Oct), Ping Pong, Foosball, Darts & Outdoor Games. The modern spacious design is filled w/ natural light, luxury comforts & new furnishings w/ Chef’s Kitchen, Weber Grill, Fireplace & Solo Stove. Ask us about nearby River Islands or day trips to ski/hike.

4.95 out of 5 average rating, 486 reviews

Cabin in Adams

Cozy Log Cabin in the Woods

Adams County TRH License #7333 Welcome to the Lucky Dog Cabin! Nestled in the trees, our charming log cabin is located 25 minutes North of the Wisconsin Dells and less than 10 minutes from Castle Rock Lake, Wisconsin River, and Quincy Bluff State Park. Come relax, unplug, and get away from it all. Enjoy the fresh air, starry nights, and peaceful nature sounds. Our 9 acre property offers a beautiful trail that leads to gorgeous sunset views, through the forest. A true nature-lover's paradise!

4.99 out of 5 average rating, 116 reviews

NEW Hot Tub! Perfect Location, Downtown Baraboo

Welcome to this thoughtfully renovated 80-year-old home that lives in the heart of Baraboo. With its perfect blend of vintage charm and modern comfort, this adorable home will be the perfect getaway. From being in the perfect neighborly location between Wisconsin Dells and Devils Lake State Park you have endless options to cater to any of your desires. You are only: 2 min to Downtown Baraboo 4 min to Circus World 11 min to Devils Lake 18 min to Wisconsin Dells 18 min to Cascade Mountain

4.9 out of 5 average rating, 210 reviews

Bungalow in Baraboo

Close to Wisconsin Dells freshly renovated home!

Beautiful bungalow located 15 minutes away from Lake Delton and all Wisconsin Dells attractions. And 4 minutes from gorgeous Devils Lake park. 15 minutes from all 3 different winter activities. Place has a beautiful sunroom, where you can enjoy a quiet neighborhood and read a book on the swing chair. House comes with a full kitchen, air fryer, coffee maker etc. Wi-Fi and electric fireplace. Fire pit with comfy chairs. We have variety of board games. House could accommodate up to 9 people.

4.92 out of 5 average rating, 260 reviews

Cabin in Merrimac

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

4.98 out of 5 average rating, 383 reviews

A cozy nook features a large window adorned with a stained glass design, allowing natural light to fill the space. A plush armchair sits beside a simple blue table, while a window seat is decorated with soft cushions, inviting relaxation in a wooden interior.

Cabin in Baraboo

Private Baraboo Bluffs Cabin with Peacocks!

This is a beautiful getaway surrounded by nature. It’s on 180 acres with walking trails. The vibe is unbeatable. You will find your peace. Hike! Relax in nature! Way up in the Baraboo bluffs and right by some of Wisconsin's favorite attractions. Minutes away from Devil’s Lake, ski hills and great hiking. Relax by the fire surrounded by nature. Nature therapy! Forest, wildflowers, and peacocks right out your window. Dogs allowed with prior approval but no other pets

4.99 out of 5 average rating, 138 reviews

A scenic view showcases the modern home nestled among vibrant trees on a Christmas tree farm. Rolling hills are seen in the background, adorned with foliage in shades of red, orange, and green. Neatly arranged rows of Christmas trees line the foreground.

Home in Merrimac

Real Christmas Tree Farm! Skiing nearby

Get lost in nature and stay where the magic grows on a real Christmas tree farm! Situated on rolling hills below the Baraboo bluffs, this 125 acre farm and nature preserve has several miles of hike/bike/ski trails, a private lake and two creeks. Modern home in a quiet rural neighborhood. Easy drive on beautiful country roads to the many attractions in the area--less than 10 minutes to Devil's Lake State Park, Lake Wisconsin as well as Devil's Head & Cascade ski areas.

A dining area features a light wood table surrounded by six chairs, positioned beneath a modern light fixture. Green walls offer a warm contrast to white accents. A decorative centerpiece holds plants, while large windows allow natural light to illuminate the space.

4.92 out of 5 average rating, 151 reviews

Green Door Getaway

Take a moment. Make yourself a cup of coffee in the bright kitchen. Find a cozy corner to read a good book. Grab the yoga mat and get your workout in while you stay. Spread out at the desk and finish your project. Connect with family and friends in the spacious living and dining areas. Enjoy a hike at a nearby State Park. Take in the thrills in the Dells. Ski down Christmas Mountain, Devil's Head or Cascade. Maggie's Green Door Getaway is ready for you to enjoy!

4.96 out of 5 average rating, 164 reviews

The open living area features a high, vaulted ceiling and wooden walls, creating a warm atmosphere. A stone fireplace stands at the center, flanked by large windows. A rustic dining table accommodates several chairs, while cozy seating arrangements are visible beside the fireplace.

Cabin in Baraboo

Devils Lake Lodge - Beautiful Lodge, Sleeps 10

Devil’s Lake Lodge is a stone’s throw from the entrance of Devil’s Lake State Park. Available for rental all year. 5 bedroom Rustic Chic Log Lodge is perfect for friends and family trips! Full kitchen, dining area, great room w/ gas fireplace, rec room w/ gas fireplace and Foosball table, lofted sitting area w/ reading nook and 3.5 baths. Stay to Hike, Bike, Swim, Run, Ski, Snowboard, Spa, Shop, Eat, Play. It's all near Devil's Lake Lodge. Enjoy the Journey.

Popular amenities for Baraboo family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 139 reviews

A scenic view from above showcases the lush, green lawn leading down to the riverbank. Cozy seating areas with umbrellas are visible on the patio, surrounded by well-maintained flower beds and a pathway that guides to the water's edge.

Home in Wisconsin Dells

Breezeway Bay - Waterfront House

4.91 out of 5 average rating, 119 reviews

Home in Wisconsin Dells

Dells Retreat - Sleeps 8 + Jacuzzi | Waterpark

4.91 out of 5 average rating, 121 reviews

A unique A-frame exterior features a mix of black wooden siding and natural brown shingles. A small patio area is visible with a round table and four black chairs, surrounded by well-kept shrubs and landscaped gravel.

Condo in Wisconsin Dells

Dells Retreat-A Romantic Haven-Jacuzzi,Pool&HotTub

4.87 out of 5 average rating, 106 reviews

A charming lakefront cabin nestled among vibrant autumn foliage. The property features a staircase leading down to the water, with a yellow kayak resting on the edge. Large windows of the cabin reflect natural light, enhancing the scenic view of trees in warm fall colors.

Cabin in Wautoma

Bayside Getaway

4.91 out of 5 average rating, 247 reviews

Cottage in Neshkoro

Nostalgic Lakehouse with Pontoon, HotTub & VHS

4.99 out of 5 average rating, 116 reviews

A recently renovated cabin is surrounded by a serene snow-covered landscape, featuring natural wood siding and large windows. In the foreground, a hot tub bubbles gently, while tall pine trees provide a wooded backdrop.

Cabin in Muscoda

Unwind at Driftless Pines Cabin

4.86 out of 5 average rating, 285 reviews

The hot tub is positioned on a deck with two glasses of red wine placed on its edge. A sunset casts warm hues over the water, while the silhouette of trees frames the scene. The distant hills create a serene backdrop.

Home in Poynette

Quietwater Cottage-Peaceful, On Water, Sandbars!

4.97 out of 5 average rating, 115 reviews

An outdoor firepit area features a circular arrangement of hanging chairs around a stone fire pit. Lush greenery surrounds the space, with a serene lake visible in the background, creating a tranquil atmosphere for relaxation and gatherings.

Home in Wautoma

Lakefront Retreat + Water Toys + Hot Tub!

Family- and pet-friendly home rentals

Bungalow in Richland Center

A modern kitchen and dining area are showcased, featuring wooden beams overhead and elegant cabinetry. A dining table is set for four, and stainless steel appliances are visible. Warm lighting casts a glow, creating a welcoming atmosphere in the space.

5 out of 5 average rating, 328 reviews

Glory View Ridgetop Bungalow

4.94 out of 5 average rating, 104 reviews

The rustic log cabin is surrounded by trees and features a green metal roof. Stone steps lead to the entrance, where a decorative flower bed enhances the natural setting. A flag gently flutters, adding a welcoming touch to the facade.

Cabin in Grand Marsh

Private Log Cabin in 10 Acre Forest

4.9 out of 5 average rating, 138 reviews

Sunset over the water is captured, with vibrant shades of orange reflecting on the surface. Silhouetted tree branches frame the scene, while hills are visible in the background under a softly clouded sky.

Guest suite in Poynette

Lake Wisconsin 2BR* GreatHiking nearby -Water View

4.92 out of 5 average rating, 181 reviews

An outdoor seating area is centered around a fire pit, surrounded by shaded trees and lush greenery. Two picnic-style tables are positioned nearby, providing ample space for gatherings. In the background, a serene lake is visible, enhancing the tranquil setting.

Cabin in Oxford

40 mins to Dells! Lakefront cabin. Kayaks included

4.91 out of 5 average rating, 105 reviews

Cabin in New Lisbon

Beautiful remodeled private cabin in the woods

4.9 out of 5 average rating, 151 reviews

Adirondack chairs are arranged along the shoreline, facing a calm lake. A large tree provides shade, while vibrant green grass extends along the bank. A small dock is visible on the water, reflecting the surrounding trees under a clear blue sky.

Holiday home in Adams

Vacation on the Lake! 15 min from Downtown Dells!

4.96 out of 5 average rating, 167 reviews

Cottage in Neshkoro

Pet Friendly Antique Schoolhouse with Fenced Yard

4.93 out of 5 average rating, 203 reviews

A quaint a-frame cabin is nestled among tall trees, with a wooden path leading to its entrance. A small porch features a wooden chair, while a sauna is positioned nearby, blending seamlessly into the forested surroundings.

Cabin in Cazenovia

Drift House, a peaceful a-frame retreat

Family-friendly home rentals with a pool

4.9 out of 5 average rating, 121 reviews

A sandy beach area stretches along the tranquil shore of Lake Delton. White lounge chairs are arranged in neat rows, facing the calm water. Gentle waves lap at the edge of the shore, bordered by lush greenery and a stone embankment.

Condo in Wisconsin Dells

Lakefront Condo - Private Beach | Pool

4.9 out of 5 average rating, 129 reviews

A log cabin-style home features a wide front deck with sturdy railings, complemented by large windows that allow natural light to flood the interior. A stone chimney and well-maintained landscaping add to the inviting exterior.

Cabin in Nekoosa

Lake Arrowhead Brown Bear Lodge Sand Valley GOLF

5 out of 5 average rating, 25 reviews

Home in Mauston

Revilo Moose Ridge (Private Pool-20 mins to Dells)

4.8 out of 5 average rating, 50 reviews

A circular, above-ground swimming pool with clear, inviting water is visible, surrounded by lush greenery. The pool deck features wooden planks, and a set of steps leads into the water, creating easy access. The tranquil lake can be seen in the background.

Cottage in Montello

Lakefront Escape, Exclusive Pool, near WI Dells

4.84 out of 5 average rating, 262 reviews

An indoor pool area is featured with large windows allowing for ample natural light. Two separate outdoor seating areas overlook the water, with patio chairs positioned along the poolside and balcony. A comfortable living room setup includes a sofa, coffee table, and window view of the surroundings.

Condo in Wisconsin Dells

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

4.98 out of 5 average rating, 58 reviews

Cabin in Lodi

Modern Cabin with pool, hot tub and outdoor sauna

4.89 out of 5 average rating, 228 reviews

A warm and inviting living area features wood paneling and exposed beams. A spacious sofa, adorned with patterned throws, faces a large flat-screen TV. Natural light filters through sliding glass doors that lead to an outdoor space. A rustic stone fireplace adds a cozy touch.

Home in Wisconsin Dells

Spacious Pine Cabin on Lake Delton