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

10.0 out of 10, Exceptional, (1)
"We had the most amazing family getaway at this beautiful lakefront house! The location was perfect, right on the water with a huge backyard. We spent so much time relaxing by the pier, lounging in comfy chairs, and taking out the canoes and paddleboat on the lake. The large patio was a favorite spot, where we enjoyed making s’mores around the firepit.The kids had an absolute blast in the game room, which had everything we could have wanted—like a mini Chuck E. Cheese right at the house! There...
Luxury 8-br Lake Home with Pool, Cinema, and Arcade in Oconomowoc on LacLaBelle

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

4 Bdrm 4 Bath Lake front Lake Sinissippi home

10.0 out of 10, Exceptional, (40)
"Myself and a group of friends stayed at Chase's home in August and we had such a great time. The house was spacious enough for all of us to be together. The weather was fantastic so we got to use the different outdoor toys and hangout in the water a lot too. Nice and private area where we felt comfortable to do as we pleased. We would definitely come back again!"
4 Bdrm 4 Bath Lake front Lake Sinissippi home

Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

10.0 out of 10, Exceptional, (35)
"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

Cozy Treehouse on the Lake

10.0 out of 10, Exceptional, (5)
"The decor of this property made me truly feel like I was in a treehouse. They were attentive to every detail. The only thing that I would change would be to have a bathroom downstairs. We stayed upstairs so it wasn’t an issue, but if another family were to stay downstairs, it might be. They’re online guidebook gave us ideas of things to do in the area, which we did and enjoyed. I would definitely return again."
Cozy Treehouse on the Lake

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

10.0 out of 10, Exceptional, (34)
"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

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!

Beautiful lakefront, Newly Remodeled Lower Level!

9.8 out of 10, Exceptional, (185)
"Perfect place on a gorgeous lake! Hustisford was adorable and we enjoyed our visit! Thank you for sharing!"
Beautiful lakefront, Newly Remodeled Lower Level!

Beautiful Family Home on Quiet Lake Ashippun

10.0 out of 10, Exceptional, (20)
"Excellent place to stay, just as described, great neighborhood."
Beautiful Family Home on Quiet Lake Ashippun

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

Eclectic Hubertus Home w/ Game Room & Fire Pit!

9.6 out of 10, Exceptional, (13)
"We thoroughly enjoyed our stay!!!"
Eclectic Hubertus Home w/ Game Room & Fire Pit!

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

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

3 Bedroom Okauchee Lake

9.6 out of 10, Exceptional, (14)
"Great location!"
3 Bedroom Okauchee Lake

Charming Horicon Cottage + Dock on Rock River

10.0 out of 10, Exceptional, (14)
"We had a relaxing week here. The area was safe and friendly."
Charming Horicon Cottage + Dock on Rock River

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

9.6 out of 10, Exceptional, (161)
"Loved the place already planning a future trip"
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

10.0 out of 10, Exceptional, (3)
"Gorgeous interior, responsive host, clear instructions. Enjoyed proximity to hiking, cafe, and arcade. "
The price is AU$744
includes taxes & fees
8 Aug - 9 Aug
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

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 AU$1,051
includes taxes & fees
28 July - 29 July
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Peaceful Horicon Studio w/ Rock River Access!

9.6 out of 10, Exceptional, (11)
"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, (19)
"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!
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 Woodland Hotel Reviews

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 Sinissippi Lake. Erin Hills Golf Course and Dodge County Fairgrounds 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.