Woodland Holiday Rentals

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Holiday Rentals in Woodland

Luxury 8-br Lake Home with Pool, Cinema, and Arcade in Oconomowoc on LacLaBelle

Luxury 8-br Lake Home with Pool, Cinema, and Arcade in Oconomowoc on LacLaBelle

4 Bdrm 4 Bath Lake front Lake Sinissippi home

10.0 out of 10, Exceptional, (40)
"Great place! Perfect for multi family vacation. Lots of activitys for the kids to play. The host is very helpful."
4 Bdrm 4 Bath Lake front Lake Sinissippi home

We're NEW! Enjoy our Serene Blue Tree House Retreat - Trails, Cozy Vibes, Lake

We're NEW! Enjoy our Serene Blue Tree House Retreat - Trails, Cozy Vibes, Lake

Beautiful lakefront, Newly Remodeled Lower Level!

9.8 out of 10, Exceptional, (184)
"Everything was just as it was described. Very comfortable for four girlfriends getting away to play bridge!! "
Beautiful lakefront, Newly Remodeled Lower Level!

Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

10.0 out of 10, Exceptional, (34)
"We had a wonderful stay at Maison La Belle - perfect location and plenty of space. Will definitely book again!"
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

3 miles from Sunburst Ski Hill. Close to great hikiing and snow mobile trails

10.0 out of 10, Exceptional, (32)
"Property was very clean, the owner was very accommodating and easy to get ahold of. We had a great stay!"
3 miles from Sunburst Ski Hill. Close to great hikiing and snow mobile trails

Cozy Treehouse on the Lake

10.0 out of 10, Exceptional, (4)
"Very beautiful place. "
Cozy Treehouse on the Lake

Okauchee Lake Vacation Rental w/ Boat Dock!

9.2 out of 10, Wonderful, (5)
"Ideal lake location near bars and town and on the water."
Okauchee Lake Vacation Rental w/ Boat Dock!

Historical Log Cabin on 80 Acres in Hartford!

10.0 out of 10, Exceptional, (1)
"We stayed for a wedding, it was close to the venue and amazingly peaceful. Our dogs loved exploring the fields. Would highly recommend a stay here."
Historical Log Cabin on 80 Acres in Hartford!

Greenstone Cottage

10.0 out of 10, Exceptional, (20)
"Loved the property . Would recommend "
Greenstone Cottage

3 Bedroom Okauchee Lake

9.4 out of 10, Exceptional, (12)
"Great location!"
3 Bedroom Okauchee Lake

Eclectic Hubertus Home w/ Game Room & Fire Pit!

9.6 out of 10, Exceptional, (13)
"We loved the property, it had plenty of room and was perfect for what we needed. On top of that, the aesthetic was just amazing and the nature and peace surrounding the house put it over the top. "
Eclectic Hubertus Home w/ Game Room & Fire Pit!

Beautiful Family Home on Quiet Lake Ashippun

10.0 out of 10, Exceptional, (17)
"Excellent place to stay, just as described, great neighborhood."
Beautiful Family Home on Quiet Lake Ashippun

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

9.6 out of 10, Exceptional, (160)
"The property had plenty of room beds are very comfortable this location is going thru remodeling which will be beautiful when finished was short on kitchen supplies which I'm sure will be replaced when finished. I would rent again."
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Charming Horicon Cottage + Dock on Rock River

10.0 out of 10, Exceptional, (13)
"We had a relaxing week here. The area was safe and friendly."
Charming Horicon Cottage + Dock on Rock River

Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

10.0 out of 10, Exceptional, (3)
"This is a nice place to stay. The bedrooms are all spacious, clean and very comfy. The communication with the host was great. I would stay here again. "
The price is NZ$1,093
includes taxes & fees
14 July - 15 July
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Private estate with tennis court and more

10.0 out of 10, Exceptional, (40)
"The property was spacious and beautiful with something for everyone! A wonderful get away for anyone."
Private estate with tennis court and more

Peaceful Horicon Studio w/ Rock River Access!

9.6 out of 10, Exceptional, (10)
"This is a really fun studio cabin with a great location. The description said “Rock River access” but that is understated: the river is literally (and I do know the correct meaning of that word) less than 10 feet from the patio door. We stayed here for the Horicon Marsh Bird Festival and the location was ideal, a very short drive to Visitors Center and other sites. We also saw warblers in the cabin’s yard and many pelicans flying over and swimming in the river!"
Peaceful Horicon Studio w/ Rock River Access!

Big Cedar Lake House: Views, 100 Ft to Water!

10.0 out of 10, Exceptional, (18)
"This house was amazing. We loved everything about our stay! We hope to visit again! The only negative I can think of is the front door is a bit difficult to lock and unlock, but this was such a small negative and would not deter us from booking this amazing property again!"
Big Cedar Lake House: Views, 100 Ft to Water!

Hugel Hutte - Cozy cabin nestled in woods - Feels like a TreeHouse

Hugel Hutte - Cozy cabin nestled in woods - Feels like a TreeHouse
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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Frequently asked questions

Can I find holiday rentals in Woodland?

Yes, there are holiday rentals close to the most popular sights in Woodland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Luxury 8-br Lake Home with Pool, Cinema, and Arcade in Oconomowoc on LacLaBelle: This holiday home rental outside of Woodland is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What can I see and do in Woodland?

While exploring the area, visit family-friendly sights like Holy Hill, or get outside and enjoy nature at Horicon Marsh Education and Visitor Center. Wisconsin Automotive Museum and Erin Hills Golf Course are a couple of places you'll find in the wider area.

What are holiday rentals like in Woodland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodland. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips or small group gatherings.