Woodland Holiday Rentals

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Holiday Rentals in Woodland

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

9.6 out of 10, Exceptional, (157)
"Enjoyed being close to the wedding venue. Samantha was available to answer any questions. The bedrooms were large and living space great for family. "
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

4 Bdrm 4 Bath Lake front Lake Sinissippi home

10.0 out of 10, Exceptional, (39)
"Great"
4 Bdrm 4 Bath Lake front Lake Sinissippi home

Beautiful lakefront, Newly Remodeled Lower Level!

9.8 out of 10, Exceptional, (176)
"We loved our 3 day weekend stay here at Rebecca’s home! This place is clean, spacious and quiet! We enjoyed the clean hot tub and watching the racing on the lake! Also enjoyed a delicious complementary bottle of wine on Valentine’s Day while doing a puzzle. Had all the amenities we needed for the weekend. Thank you so very much! We appreciate all the communication and added advice of things to do in the area!Highly recommend the stay here! "
Beautiful lakefront, Newly Remodeled Lower Level!

Beautiful Family Home on Quiet Lake Ashippun

10.0 out of 10, Exceptional, (12)
"We got together to celebrate one of our siblings birthday. My family is from all over and four flew into Milwaukee airport. It was a convenient location to do this. House is beautiful and roomy. Had 6 adults staying and all were comfortable and had plenty of space. We hosted our sibs party and all had a great time and were impressed with the house. Would recommend this property."
Beautiful Family Home on Quiet Lake Ashippun

Eclectic Hubertus Home w/ Game Room & Fire Pit!

9.6 out of 10, Exceptional, (8)
"Very clean, spacious property. Worked out well for us and our grown children and grandchildren. A couple of issues I will mention are no extra linens or towels were provided. Only what was out on the bed and one towel per person, which with young children could become an issue. The biggest thing we noticed was the lack of smoke or carbon monoxide detectors. Not one that we could find. Not sure how this can be possible for a property that is clearly used as a business. If not for those things, we...
Eclectic Hubertus Home w/ Game Room & Fire Pit!

Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

10.0 out of 10, Exceptional, (15)
"Really great location. Excellent accommodation. Clean very well equipped easy check in and out process. Only recommendation a few more blankets for beds. I’m from Fl and was in the teens needed a few extra lol. Thank you for a great home like atmosphere we were in town for our best friends funeral. "
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

Greenstone Cottage

10.0 out of 10, Exceptional, (16)
"Loved the property . Would recommend "
Greenstone Cottage

3 Bedroom Okauchee Lake

9.2 out of 10, Wonderful, (10)
"Property description is accurate, yes you are staying above a very popular bar so you will hear the music late into the evening. We were there for a holiday weekend so this was just fine for us and our adult kids! Hosts communicated promptly and even provided a waffle bar and snacks! Loved being able to go downstairs and order food and drinks. We also walked to nearby restaurants, a perfect location to experience some lake life. Thank you!"
3 Bedroom Okauchee Lake

Amazing Cottage Big Cedar Lake

10.0 out of 10, Exceptional, (4)
"This home was best stocked VRBO I have ever stayed in! Great deck for morning coffee, dinner and games. Easy walk to the water! "
Amazing Cottage Big Cedar Lake

Lakefront house! SUP and Kayak use included. Boat available for rent! Near golf!

9.4 out of 10, Exceptional, (9)
"Had a great time! Great location!"
Lakefront house! SUP and Kayak use included. Boat available for rent! Near golf!

Rock River Retreat Boathouse Bungalow...Relax, Refresh, and Enjoy this Zen Den

10.0 out of 10, Exceptional, (5)
"Beautiful property and close to a lot of great things"
Rock River Retreat Boathouse Bungalow...Relax, Refresh, and Enjoy this Zen Den

Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

10.0 out of 10, Exceptional, (31)
"Charming delightful immaculate beautiful comfortable home we had the pleasure of staying in . It just felt like home . Nothjng was overlooked the attention to detail incredible . Fantastic location within walking distance to downtown the lake the restaurants . Communication with owner was outstanding "
The price is AU$1,374
includes taxes & fees
3 Mar - 4 Mar
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

Rock River Haven - charming, spacious, peaceful

10.0 out of 10, Exceptional, (32)
"My teenage children and I stayed for two nights and enjoyed all the games, hot tub and beautiful view of the river. Thank you! "
Rock River Haven - charming, spacious, peaceful

Private estate with tennis court and more

10.0 out of 10, Exceptional, (39)
"Our family had a wonderful Thanksgiving holiday and weekend retreat. We got to see a flock of turkeys in the front yard on Thanksgiving morning! The house and property was as advertised. Plenty of space for our large party. The kitchen was well stocked which helped with our holiday meal prep. Family loved playing pool and the video games. Great place to stay! We will be back!"
Private estate with tennis court and more

Relax & Reboot in this Charming 2-Bedroom Townhome

The price is AU$391
includes taxes & fees
19 Mar - 20 Mar
Relax & Reboot in this Charming 2-Bedroom Townhome

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

10.0 out of 10, Exceptional, (2)
"We were able to be more freely in regards of cooking breakfast real eggs, do laundry, watched TV more comfortable better than in a hotel was the experience for us "
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

Luxury Vacation Smart Home w/ Hot-tub, Home Theatre & XBOX

The price is AU$721
includes taxes & fees
19 Feb - 20 Feb
Luxury Vacation Smart Home w/ Hot-tub, Home Theatre & XBOX

Stylish Historic Upper- A Short Walk to Downtown, Lakes & Restaurants

10.0 out of 10, Exceptional, (29)
"The Blue Bell was a lovely historic home a short walk from downtown Oconomowoc. The property has lots of character and has been renovated to retain its charm and also have the conveniences travelers desire. Plenty of room to relax and also working areas for remote workers. The hosts were very responsive. The kitchen, bathrooms, and coffee nook were all well stocked. Would highly recommend this property and these hosts!"
Stylish Historic Upper- A Short Walk to Downtown, Lakes & Restaurants

Okauchee Lake Vacation Rental w/ Boat Dock!

9.6 out of 10, Exceptional, (4)
"The good: Outside: the dock, swim pad, accessories, deck, outdoor furniture, neighborhood, location. Inside: everything worked, A/C was mostly sufficient with fan blowing into bedroom. The not so good: there is clearly a known ant problem on the center peninsula of the kitchen, saw spray in the utility room. Could use a thorough going-through for bugs, cobwebs, pet hair e Overall: for the location and price, this is a decent value if you're spending most of your time outside. Bring your own...
Okauchee Lake Vacation Rental w/ Boat Dock!

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

10.0 out of 10, Exceptional, (18)
"We enjoyed the peace and quiet and the lovely home!"
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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Other types of properties in Woodland you may be interested in

AmericInn by Wyndham Beaver Dam

2.5 star property
9.0 out of 10, Wonderful, (452)
"We stay here annually and the staff is amazing and the hotel is fabulously quaint, quiet, and cozy. The new renovations are fantastic too!! "
The price is AU$155
includes taxes & fees
23 Feb - 24 Feb
AmericInn by Wyndham Beaver Dam

Country Inn & Suites by Radisson, West Bend, WI

2.5 star property
8.2 out of 10, Very good, (730)
"Easy access to shopping and highway"
The price is AU$148
includes taxes & fees
23 Feb - 24 Feb
Country Inn & Suites by Radisson, West Bend, WI

TownePlace Suites by Marriott Milwaukee West Bend

2.5 star property
9.4 out of 10, Exceptional, (169)
"The staff and hotel are both top notch. One of the cleanest and nicest hotels I've stayed at ever. Every member of the staff went out of their way to assist our group."
The price is AU$196
includes taxes & fees
2 Mar - 3 Mar
TownePlace Suites by Marriott Milwaukee West Bend
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.

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?

Beautiful lakefront, Newly Remodeled Lower Level!: This holiday home rental outside of Woodland is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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. Erin Hills Golf Course and Horicon Marsh 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.