Boscobel Holiday Rentals

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Holiday Rentals in Boscobel

Amish-Built Cabin in the Driftless Area
10.0 out of 10, Exceptional, (47)
"Had a great time in SW Wisconsin!"
Amish-Built Cabin in the Driftless Area
The Guest House
10.0 out of 10, Exceptional, (21)
"We found the property clean and perfect for our needs. The host was gracious and the loft was well supplied. They sell farm fresh beef and eggs. We had the eggs for breakfast each morning, what a treat. We would recommend Hollow Rule to anyone staying in the area."
The price is NZ$222
includes taxes & fees
10 Jun - 11 Jun
The Guest House
Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!
9.6 out of 10, Exceptional, (44)
"Absolutely beautiful, quiet farm location. Lodgings are scrupulously clean and beautifully decorated. The bathroom was bigger than my bedroom! Lovely host gave us a quick tour of the property, and we met a 2-week old filly. We will stay here again!"
The price is NZ$291
includes taxes & fees
12 Jun - 13 Jun
Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!
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The Harwood House
10.0 out of 10, Exceptional, (29)
"We stayed 3 nights, and had a great time. Everything was as described in the listing. The sun porch was nice, and really loved the coffee bar. We stayed when it was very warm for this time of year and the upstairs window air conditioner was a life (sleep) saver! Don't hesitate to book this property."
The Harwood House
SereniTree Cabin - Modern Rustic Getaway tucked in the trees
10.0 out of 10, Exceptional, (62)
"Super good time! Great cabin! The deck was amazing! We had loads of fun just hanging out, talking, and laughing! Thank you for a great weekend!"
SereniTree Cabin - Modern Rustic Getaway tucked in the trees
Maplewood Cabin: Secluded Romance with Private Hot Tub while Star Gazing.
10.0 out of 10, Exceptional, (16)
"My wife and I were looking for a relaxing cabin and this place was the exact place we were looking for. Great location. The cabin was comfortable and clean. The hot tub was the icing on the cake. We look forward to another visit."
Maplewood Cabin: Secluded Romance with Private Hot Tub while Star Gazing.
Romantic or a couple's getaway, seclusion and privacy in the Driftless region
10.0 out of 10, Exceptional, (16)
"Wonderful property, exactly what we were looking for in a quiet, relaxing weekend away!"
Romantic or a couple's getaway, seclusion and privacy in the Driftless region
Cozy Log Cabin next to the Mississippi River
9.6 out of 10, Exceptional, (62)
"This cabin and property were a perfect choice for our fishing getaway. We were a little concerned about the available space for 4 large adults in the cabin as well as two boats and two trucks, but everything turned out great. Cabin ended up being perfect. Location to the boat ramp was really good and we were able to fit our boats and trucks at the location. We would have preferred a bit more space for parking, but the road wasnt very busy and it all worked out just fine. Cabin is stocked with...
Cozy Log Cabin next to the Mississippi River
Wexford Hollow... 6 Bedroom Cabin w/ Pool & Hot Tub
The price is NZ$507
includes taxes & fees
5 Jun - 6 Jun
Wexford Hollow... 6 Bedroom Cabin w/ Pool & Hot Tub
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
10.0 out of 10, Exceptional, (403)
"The cabin was great. Loved it all. Been a long time since we were in Wisconsin and forgot about mosquitoes but they were very welcoming. Really enjoyed our stay here"
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Newly remodeled cozy retreat. Pet friendly & 3 minute walk to the river!
10.0 out of 10, Exceptional, (8)
"Was clean and had everything we needed. We had a great time exploring the area and Wyalusing State Park."
Newly remodeled cozy retreat. Pet friendly & 3 minute walk to the river!
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View
9.8 out of 10, Exceptional, (126)
"Small but cozy place. Was very peaceful and quiet at night. Looking forward to staying again in the future"
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
10.0 out of 10, Exceptional, (17)
"We came to enjoy a weekend away from worries and we very much accomplished it! We enjoyed some local food and walked along the river in between playing games at the cabin. The cabin itself was very clean and cozy!"
Newly remodeled log cabin next to beautiful Wisconsin River- Rivers Edge Cabin
Copper Roof Cottage
10.0 out of 10, Exceptional, (27)
"Perfect place to stay for a weekend getaway in Prairie du Chein!"
Copper Roof Cottage
Newly updated historical home
9.8 out of 10, Exceptional, (32)
"Loved the rental! Super clean and modern! Great location and hosts!"
Newly updated historical home
Rural Cabin in the Woods
9.2 out of 10, Wonderful, (24)
"My family and I thoroughly enjoyed our stay at this peaceful little cabin. It was a great spot to relax and give our kids and dogs some room to run around for the weekend with plenty of recreational options a short drive away."
The price is NZ$331
includes taxes & fees
7 Jun - 8 Jun
Rural Cabin in the Woods
Ohio Street Retreat
10.0 out of 10, Exceptional, (26)
"Many listings can seem to over-sell the condition of the property, or the scope of other benefits the property offers to people staying there. Neither of these things happened for me and my wife during our stay here. I believe the description was undersold in the listing, since the property more than exceeded our expectations. Extremely clean, and neat. All listed amenities were present, and those that we accessed were 100% useful. Definitely recommend this location to anyone considering a stay...
The price is NZ$247
includes taxes & fees
6 Jun - 7 Jun
Ohio Street Retreat
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
10.0 out of 10, Exceptional, (118)
"A beautiful cabin on a beautiful piece of land. As described in the listing and absolutely peaceful. This is our second time staying here and we will be back."
The Driftless Escape! Modern, large cabin/57 private acres in WI drift less area
Relax with beautiful views overlooking the Wisconsin River
10.0 out of 10, Exceptional, (30)
"Home was nicely remodeled and clean. Even the 3 car garage was quite clean. Nice view of flowing river."
Relax with beautiful views overlooking the Wisconsin River
Unique! A renovated old railroad depot turned into a cozy cottage.
10.0 out of 10, Exceptional, (93)
"The house itself is so cool and unique- really beautiful! I also so much appreciate that the beds are comfy, nice quality sheets and pillows, and nice fluffy bath towels. Sometimes rental owners skimp on those- not here. Also had a little snafu with the house- nobody’s fault- and the owners were so kind and responsive to my needs. They are wonderful and attentive people and truly care that their guests have an amazing experience."
Unique! A renovated old railroad depot turned into a cozy cottage.
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See all available properties in Boscobel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Boscobel you may be interested in

AmericInn by Wyndham Boscobel
2.5 star property
8.8 out of 10, Excellent, (350)
"Comfortable and clean room, delicious breakfast."
The price is NZ$151
includes taxes & fees
16 Jun - 17 Jun
AmericInn by Wyndham Boscobel
The Guest House
10.0 out of 10, Exceptional, (21)
"We found the property clean and perfect for our needs. The host was gracious and the loft was well supplied. They sell farm fresh beef and eggs. We had the eggs for breakfast each morning, what a treat. We would recommend Hollow Rule to anyone staying in the area."
The price is NZ$222
includes taxes & fees
10 Jun - 11 Jun
The Guest House
Amish-Built Cabin in the Driftless Area
10.0 out of 10, Exceptional, (47)
"Had a great time in SW Wisconsin!"
Amish-Built Cabin in the Driftless Area
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Boscobel holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Boscobel. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Boscobel. Seeing all the best attractions is bound to make you fall in love with Boscobel. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Boscobel short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Boscobel?

Yes, there are holiday rentals in Boscobel close to WI River Outings, or you can select a more secluded option if you're looking for a relaxing stay. Boscobel is known for its restaurants.

What are some of the best holiday rentals that Boscobel has to offer?

Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!: This holiday home rental outside of Boscobel is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What can I see and do in Boscobel?

Family-friendly attractions include WI River Outings, whereas Wisconsin River is a spot to enjoy the outdoors. Kickapoo River and Eagle Cave are a couple of places you'll find in the wider area.

What are holiday rentals like in Boscobel?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Boscobel. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.

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