Holiday rentals in Bosstown

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Top-rated holiday rentals in Bosstown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in De Soto

4.93 out of 5 average rating, 54 reviews

Paradise Point sleeps 4 Hot Tub

1 bedroom 1 bath with loft. Cozy home where you can see Paradise. This memorable place is anything but ordinary. Views for miles of the Mississippi River, bluff tops and you can soar with the Eagles. What a place to relax in the newly added hot tub while you enjoy the view in what is call "God's Country". This is promised to be a one of a kind view. The Deck with comfortable outdoor seating Located in the heart of WIsconsin's Driftless Region. New workout center for all our guest to use.

Guest favourite

Home in New Lisbon

5 out of 5 average rating, 28 reviews

Retreat on the Beach! EV Friendly! Hot tub!

Escape the craziness of life in this new construction home. This Beach Cottage home is perfect for your family to enjoy all Wisconsin seasons. Beach Lake is a clear Six acre private lake with a sandy bottom located near Buckhorn State Park, Castle Rock Lake, lots restaurants, and is only a 30-minute drive to the Wisconsin Dells. Our home has 4-bedrooms and 2 full baths, Full Kitchen, huge basement, patio, deck, private beach, insulated/heated garage with a EV charger. Hot tub October 2023.

Guest favourite

Bungalow in Richland Center

5 out of 5 average rating, 279 reviews

GloryView Ridgetop Bungalow

Farmhouse Bungalow sits on top of a ridge in the Southwest WI driftless area, boasting spectacular views. A site that works for anyone from a relaxing retreat to a great spot for adventures. Fall photography dream, cyclists paradise, star gazing/campfire, hiking, kayaking, canoeing, fly fishing, Frank Lloyd Wright, WI Dells and other local attractions. The home was completely renovated with all the modern conveniences but the Farmhouse charm. A sleeping loft adds additional functionality.

Guest favourite

Cottage in Harpers Ferry

4.89 out of 5 average rating, 163 reviews

Harpers Slough Cottage w/ Hot tub

Stunning inside and out with amazing river views! 80 feet of riverfront with private covered dock. Updated 3 bedroom and 2 bath home with views from balcony or the screened in porch with access from the master bedroom. Covered balcony and concrete beneath the entire property for lounging or activities. 30 mins from Lansing, Prairie Du Chien, Marquette, and Waukon. Also including the parks Pikes Peak, Spook Cave, and Yellow River Forest. Awesome for boating, fishing, and duck/goose hunting.

Guest favourite

Cabin in New Lisbon

4.93 out of 5 average rating, 134 reviews

Cozy, dog friendly, cabin, Castle Rock Lake area.

Close to Castle Rock Lake, 25 minutes to WI Dells, shopping, golf courses, fishing, casino, nightlife, beaches, and so much more. Relax and unwind in our cozy log cabin which is located on a dead road on 4 beautifully wooded acres. Enjoy the peace and quiet, or the lake is just 3 minutes away where you can enjoy boating, fishing and great restaurants and weekend entertainment featuring live music. Our place is good for couples, solo adventurers, business travelers, and families (with kids).

Guest favourite

Cabin in Ferryville

4.98 out of 5 average rating, 50 reviews

EAGLEVIEW NEST - hot tub, GRANDVIEW of Mississippi

THE VIEW of the Mighty Mississippi River from this cabin is absolutely amazing! We're so excited to offer our sixth vacation rental property for our guests to choose from. We know what you're looking for -- hot tub, fire pit, king bed -- and so much more. We're proud of our places and invest a lot into exceeding all expectations. It's a great place use as your home base for exploring our gorgeous Driftless Region. Don't wait, get your reservation in before it's booked up for 2021.

Guest favourite

Home in Spring Green

4.94 out of 5 average rating, 67 reviews

Hot Tub/$0 Cleaning Fee/Golf Course/The Hemlock

Our 4 bedroom, 2.5 bath home in downtown Spring Green, Home to Frank Lloyd Wright’s Taliesin, American Players Theater, the House on the Rock, and Tower Hill State Park, the vibrant village of Spring Green is a place where nature and art meet. Just 45 minutes from Madison, And the Dells Waterpark. Do You enjoy Golfing Or snow mobile Riding? Relax with the whole family at this peaceful place to stay. walk to downtown or the Rec Park with soft ball diamond and skate board Park.

Guest favourite

Home in New Lisbon

5 out of 5 average rating, 29 reviews

Lakehouse on Beach Lake w/Hot Tub & Screened Porch

Experience the ultimate beachfront retreat with a stunning lakeview, luxurious hot tub, screened porch, private sandy beach, and a cozy fire pit under the stars. WisCottage is a luxurious 5-bedroom vacation rental promising an unforgettable escape with breathtaking lake views, indulgent amenities, and endless opportunities for relaxation and adventure. This premier beachfront retreat is nestled conveniently near the picturesque shores of Castle Rock Lake and Wisconsin Dells.

Superhost

Cabin in Friendship

4.79 out of 5 average rating, 29 reviews

Bluff View Hideaway

Slow down at this peaceful and centrally-located place - On 5 acres with over 3000 DNR acres around it. Bring your pet too. Lg fenced in dog area w/doggie door just off the screen porch. 5 miles to Castle Rock Lake, 20 miles to WI Dells. Fishing, Horseback riding, ATV trails, & petting zoos nearby. Boat/kayaks/Tubing rentals nearby. Fantastic public hike on trails to the bluffs/tower that is in view from the cabin. Rest, Relaxation, and the songs of nature await.

Superhost

Chalet in La Crosse

4.79 out of 5 average rating, 191 reviews

Bayfront Chalet on Richmond Bay

Waterfront Property- 3 bedrooms, 2 full bath home - You will be amazed at the views from this extravagant French Island house on Richmond Bay. It features JennAir stainless steel appliances including dishwasher, laundry, central air, free Wifi, large deck and use of a nice sized dock for boating, kayaking or jet skiing. These items (boat,kayak,water crafts)are not included with . Airbnb. Fireplace is for aesthetics. Less than a 10 minute drive to the La Crosse Center.

Guest favourite

Cabin in Bagley

4.91 out of 5 average rating, 174 reviews

**Cozy & Dog Friendly** Rustic Cabin Retreat

Relax and recharge at this country getaway which is tucked amongst trees and the rolling hills. Surround yourself with nature while also having easy in and out access! This makes it a breeze to come and go as you please and explore all southwest Wisconsin has to offer! Ready for the whole family to enjoy, along with their furry friends. *9 minute drive to Wyalusing State Park *10 minute drive to Bagley / Wyalusing Public Beach *16 minute drive to Prairie du Chien

Guest favourite

Home in Lynxville

4.83 out of 5 average rating, 206 reviews

Highland Hideaway

A cozy, secluded two bedroom cabin located in the driftless region with incredible views of the Mighty Mississippi!!! If your looking for peace, quiet, and beautiful sunsets this is your place. Only 20 minutes from Wyalusing state park, The Effigy Mounds (sacred Indian Burial Grounds) Pikes Peak and Historic Villa Louis. This beautiful cabin centers you 30 miles from amazing hiking, fishing, hunting and nature for a weekend of disconnecting from busy life.