A calm lake surrounded by autumn-colored trees and rocky terrain.

Boscobel Holiday Rentals

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Our top choices for Boscobel holiday rentals

1. Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (14 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
The price is NZ$266
includes taxes & fees
15 Nov - 16 Nov
Crooked Creek - Relaxation Cabin

2. Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (16 reviews)
"Worked well for our 2-day stay. "
United States
John V.
The price is NZ$335
includes taxes & fees
29 Nov - 30 Nov
Crooked Creek - Serenity Cabin

3. Crooked Creek - Rustic Cabin

Crooked Creek - Rustic Cabin
Boscobel
9.6 out of 10, Exceptional, (13 reviews)
"very nice and quiet place to hang your hat."
United States
reuben n.
The price is NZ$302
includes taxes & fees
15 Nov - 16 Nov
Crooked Creek - Rustic Cabin

4. Charming 3-bedroom upstairs apartment in welcoming Fennimore.

Charming 3-bedroom upstairs apartment in welcoming Fennimore.
Fennimore
9.4 out of 10, Exceptional, (6 reviews)
"The property was exactly as described. The decor was super cute and the beds were very comfortable! Highly recommend this property!"
United States
Christina
The price is NZ$297
includes taxes & fees
17 Nov - 18 Nov
Charming 3-bedroom upstairs apartment in welcoming Fennimore.

5. Blackbear Lodge, 3 bedroom cabin with Hot Tub Jacuzzi

Blackbear Lodge, 3 bedroom cabin with Hot Tub Jacuzzi
Harpers Ferry
Blackbear Lodge, 3 bedroom cabin with Hot Tub Jacuzzi

6. Sunset Studio, Amazing River Views, HOT TUB! New Listing!

Sunset Studio, Amazing River Views, HOT TUB! New Listing!
Eastman
9.4 out of 10, Exceptional, (22 reviews)
"Loved it will be back!"
United States
Nick C.
The price is NZ$495
includes taxes & fees
15 Nov - 16 Nov
Sunset Studio, Amazing River Views, HOT TUB! New Listing!

7. Highland: Driftless Fun Awaits

Highland: Driftless Fun Awaits
Highland
10.0 out of 10, Exceptional, (1 review)
"Great property. Had everything we needed. Highly recommend. "
United States
Joshua
The price is NZ$364
includes taxes & fees
7 Dec - 8 Dec
Highland: Driftless Fun Awaits

8. Ohio Street Retreat-hot tub, pool, massage chair

Ohio Street Retreat-hot tub, pool, massage chair
Prairie du Chien
10.0 out of 10, Exceptional, (100 reviews)
"Nice stay, will stay again."
United States
Thomas D.
The price is NZ$357
includes taxes & fees
15 Nov - 16 Nov
Ohio Street Retreat-hot tub, pool, massage chair

9. Private location 2 bedroom mobile home great view of the Mississippi River

Private location 2 bedroom mobile home great view of the Mississippi River
Lynxville
9.8 out of 10, Exceptional, (41 reviews)
"Very clean and an excellent view of the Mississippi River"
United States
Joshua l.
The price is NZ$258
includes taxes & fees
25 Nov - 26 Nov
Private location 2 bedroom mobile home great view of the Mississippi River

10. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
The price is NZ$352
includes taxes & fees
19 Nov - 20 Nov
River Road Retreat

11. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (55 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
The price is NZ$499
includes taxes & fees
17 Nov - 18 Nov
Cabin on the Kickapoo

12. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (42 reviews)
"Had everything we needed."
United States
Tawnia
The price is NZ$361
includes taxes & fees
25 Nov - 26 Nov
River Road Getaway

13. Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route

Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route
Eastman
9.2 out of 10, Wonderful, (36 reviews)
"We had a good stay, we loved the animals and the hot tub"
United States
Brooke N.
The price is NZ$555
includes taxes & fees
15 Nov - 16 Nov
Hot Tub! Cowboy Retreat! SW Wisconsin Driftless Region on UTV Route

14. Copper Creek Getaway Sleeps 6 Hot Tub

Copper Creek Getaway Sleeps 6 Hot Tub
Seneca
10.0 out of 10, Exceptional, (2 reviews)
"Great area to explore, lots of friendly people. Enjoyed the trip and where we stayed was a great relaxing place."
United States
Cindy B.
The price is NZ$618
includes taxes & fees
16 Nov - 17 Nov
Copper Creek Getaway Sleeps 6 Hot Tub

15. Timber Ridge Lodge -HOT TUB- POOL

Timber Ridge Lodge -HOT TUB- POOL
Harpers Ferry
9.0 out of 10, Wonderful, (38 reviews)
"Great place. Plenty of room for all 6 of us. Enjoyed all the amenities."
United States
Tommy H.
The price is NZ$500
includes taxes & fees
16 Nov - 17 Nov
Timber Ridge Lodge -HOT TUB- POOL
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.
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Top Boscobel Hotel Reviews

Find out more about Boscobel

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?

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin: This holiday home rental outside of Boscobel is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.