Pet-friendly holiday rentals in Baraboo

Driftless Glamping on a Bluff

Rustic camping in the Driftless Region on the top of a bluff in a 20ft Bell Tent ,extra tent with queen air mattress. Relax without having to pack, set up , tear down and put away when you get home, more time to do things you enjoy. Go trout fishing, walk or ride the Omaha Trail Tunnel, Elroy- Sparta Trail, or the 400 Trail. Necedah Wildlife Refuge, Buckhorn, Castle Rock, Wisconsin Dells, Amish scenic drive, and Wildcat State Park with canoeing down the Kickapoo River are all within 30 minutes.

Outdoor spaces · Pets · Access

Cool quiet country cabin on boulders and 120 acres

Funky, tidy 23 year old country cabin on 120 acres of farmland & woods in a private, quiet rural setting. It's cozy, 950 sq ft, built with stone and wood. Open concept with a two story fireplace, porch fireplace, firepit, and open loft for sleeping (1 bed), with spiral stairs, lots of windows, walnut floors and trim, oak beams and pine kitchen tops. Shower is big and open, with doors opening to a back deck for outdoor showering. Beautiful covered porch overlooking rolling meadows and woods.

Pets · Walkability · Decor

Private Log Cabin in 10 Acre Forest

Take it easy at this rustic authentic log cabin. Deep in the woods, your private haven awaits on over 10 acres to hike or hunt. Enjoy the stunning rock formations in the backyard and shady trees welcoming you along the drive to this peaceful escape! Sit on the wrap around deck and watch the deer, turkey and other wildlife or build a bonfire to warm yourself on the cool evenings. This is a truly unique and tranquil getaway. Less than 20 minutes to all the action of The Wisconsin Dells.

Outdoor spaces · Walkability · Value

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

Walkability · Outdoor spaces · Check-in

Oasis, NEW Hot Tub, Fire-pit lounge and Coffee Bar

Wild Peak Cottage a newly renovated A-Frame, just a hop, skip, and a jump from Castle Rock Lake, less than 1 mile! Brand NEW hot tub as of 2/18/2026!! Gather around the fire pit, swing on hammocks, roast marshmallows, and create lasting memories. Relax in our large hot tub, under the stars surrounded by pine trees Walking distance (less than 1 mile) to Castle Rock Lake, 25 minutes to Wisconsin Dells, and a short distance to hiking, fishing, wineries, and so much more!

Pets · Outdoor spaces · Indoor spaces

Cabin in the woods with a pond and pet friendly!

Escape to Nature on 20 Private Acres! Unwind at our peaceful cabin on 20 acres of Wisconsin woods. Enjoy the private stocked pond with a kayak and paddle boat, fishing, bonfires, and trails. The cabin has 3 private bedrooms (1 king, 2 queens) plus a loft queen bed open to the living room, 2 full baths, perfect for families or friends. 30 min to Wisconsin Dells, 10 min to downtown Montello, 30 min to Cascade Mountain, 40 min to Devil’s Head Resort.

Outdoor spaces · Pets · Beach

Wild Rose Ranch Guest house

Enjoy the quiet peaceful nature of the Baraboo Bluffs and the convenience of being close to WI Dells(15 min), Baraboo, ( 5 min), Baraboo Bluffs,(back yard), Devils Lake( 5 min), Cascade Mountain(10 min), Devils Head(10 min), Circus World(3 min). Good for couples, families and dogs (pet fee$200). Backyard views of the Baraboo bluffs. UTV route access from the house. Additional $20 fee/guest/night after 6 guests.

Pets · Outdoor spaces · Getting around

Dog-Friendly Mighty Pine Cabin Escape w/Sauna

We welcome you to Ridge & Valley Hospitality where our overall goal is to create a place of rest and relaxation. We use beautiful design aesthetics and intentional planning to weave together a property that will clear your mind, and stimulate your senses. Connect with nature in the phenomenal Driftless Area of SW Wisconsin close to House on the Rock, Wisconsin Dells, and more. Bring your canine companion too.

Outdoor spaces · Pets · Heating

Quietwater Cottage-Peaceful, On Water, Sandbars!

Quietwater Cottage is conveniently located on the Lake Wisconsin waterfront midway between Madison and the Wisconsin Dells, just 1-1/2 hours from Milwaukee, 3 hours from Chicago. Great place to come back to after a day of hiking for a soak with a GREAT view of nature! Watch crimson sunsets from the 16' x 25' deck. We are pet friendly for well behaved dogs with a $25/night pet fee (maximum of 2 dogs).

Outdoor spaces · Walkability · Backyard

Hot Tub, Private Log Cabin Lazy Bear Welcomes You!

We've pulled out all the stops for you! This beautiful 3 level, 3 bedroom, 2 full bath home has over 1800 square feet to stretch out in. You'll be greeted with pretty flooring and a gorgeous all new kitchen complete with perfect granite tops and brand new appliances. Lazy Bear is a full (real) log home surrounded by woods and located on a dead-end road with just a few other homes down the road.

Pets · Outdoor spaces · Accuracy

The Loch at WhiskyWood - secluded cabin + hot-tub

Tucked within the secluded pine forest of Whiskeywood, The Loch is a cozy Scottish-inspired retreat designed for rest and quiet escape. Surrounded by towering pines, it offers fresh air, peaceful privacy, and a relaxing woodland atmosphere—perfect for unwinding, reconnecting with nature, and enjoying the charm of a Highlands-inspired getaway. 🌲🏴󠁧󠁢󠁳󠁣󠁴󠁿

Walkability · Pets · Backyard

Spring Bank Cabin

Spring Bank Cabin is an 18'x42' off the grid cabin tucked in amongst the rolling hills of the driftless area, sitting on 13 acres of open meadow and forested land with a 28' covered porch! It's equipped with solar panels and a generator, and has a full functioning bath and kitchen. Ask us about our discount for children 10 and under!

Walkability · Outdoor spaces · Bathroom