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Top Holiday Rentals in Woodland

Beautiful lakefront, large deck, family friendly!
9.8 out of 10, Exceptional, (161)
"Had a great stay. Wished it could have been longer."
Beautiful lakefront, large deck, family friendly!
Snow and ski sports
3 miles from Sunburst Ski Hill. Close to great hikiing and snow mobile trails
10.0 out of 10, Exceptional, (23)
"Cozy getaway located in a quiet spot with a beautiful view. Nancy was an amazing host. Thank you for everything!"
3 miles from Sunburst Ski Hill. Close to great hikiing and snow mobile trails
Exterior
Greenstone Cottage
10.0 out of 10, Exceptional, (6)
"Greenstone Cottage was clean and comfortable with a well-stocked kitchen. We appreciated being able to walk near the lake and to restaurants in downtown Oconomowoc. Property manager was easy to reach and helpful."
Greenstone Cottage
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Smart TV
3 Bedroom Okauchee Lake
10.0 out of 10, Exceptional, (7)
"This property was great! Exactly as described. The music on the weekend did not interfere with relaxing or sleeping. We were even greeted at the bar with a round of free drinks! Would definitely Saturday again if we are in the area!"
3 Bedroom Okauchee Lake
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Rock River Haven - charming, spacious, peaceful
10.0 out of 10, Exceptional, (26)
"Our stay was wonderful. Clean, cozy and the owners were very accommodating, we will surely be visiting again when we are in town. Perfect find, don't pass it up if you are in need of a place to stay while in Watertown. MJ and Andy thank you very much."
Rock River Haven - charming, spacious, peaceful
Smart TV
Amazing Cottage Big Cedar Lake
Amazing Cottage Big Cedar Lake
Property grounds
Eclectic Hubertus Home w/ Game Room & Fire Pit!
10.0 out of 10, Exceptional, (2)
"The house and property are amazing. We had four adults and four children on our trip. The house is huge so there is plenty of space for everyone. The place feels like its right out of the Brady Bunch, in a good way. Would definitely book this property again."
Eclectic Hubertus Home w/ Game Room & Fire Pit!
Aerial view
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!
9.6 out of 10, Exceptional, (150)
"Pictures were accurate. If you have a large group would advise bringing larger pans for cooking as the ones here were small and limited in numbers. The water softener would probably help eliminate or minimize the sulfur smell from the water, however, there was no salt in the brine tank to make it work. So if that is a concern I would also advise bringing bottled water. We stayed here for my daughter’s wedding and it was very convenient. Also host was very prompt in response times."
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!
Private kitchen
Beautiful Family Home on Quiet Lake Ashippun
Beautiful Family Home on Quiet Lake Ashippun
4 Bdrm 4 Bath Lake front Lake Sinissippi home
10.0 out of 10, Exceptional, (36)
"Awesome place to stay on the lake. Property had lots of beds to sleep on and things to do. Highly recommend!"
4 Bdrm 4 Bath Lake front Lake Sinissippi home
Smart TV
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews
10.0 out of 10, Exceptional, (13)
"We thoroughly enjoyed our stay. Great house, perfect view, brilliant location. We thank you so much for the festive decorations and tree! We’ll be back to see you one summer…"
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews
Dining
Peaceful Horicon Studio w/ Rock River Access!
10.0 out of 10, Exceptional, (2)
"Needed a change of scenery for a couple of days and this was perfect! Quaint, cute and a delight. Will be visiting again."
Peaceful Horicon Studio w/ Rock River Access!
Terrace/patio
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
10.0 out of 10, Exceptional, (21)
"CEO1: "It was such a cool house! Accommodations were excellent and the home was beautiful." CEO2: "Very nice house with wonderful attention to detail. Perfect for our purpose.""
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle
Fridge, oven, dishwasher, coffee/tea maker
2 bedrooms, 1 bathroom, full kitchen, full laundry, walk-in pantry
The price is £149
includes taxes & fees
9 Jun - 10 Jun
2 bedrooms, 1 bathroom, full kitchen, full laundry, walk-in pantry
Fridge, microwave, oven, stovetop
Cozy cottage on okauchee lake
Cozy cottage on okauchee lake
View from property
Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!
4.0 out of 10, (1)
"The boats are sit on tops, not kayaks. The property was not prepared when I arrived. Leaks in roof, I could see through roof . Wet floor in bathroom. No towels were out. I had to vacuum up a broken dish upon my arrival. Dirty sponges in sink. And the deck drops off to lawn with no stairs. No one but a giant would call that a step. And the dock is unsafe, boards have holes and end was unsecure."
Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!
Property grounds
Private estate with tennis court and more
10.0 out of 10, Exceptional, (29)
"Amazing home ! Just perfect for a large group and so many things to do on the property ! Greg was available for anything we needed we will be back for sure ."
Private estate with tennis court and more
Exterior
✨Chic Retreat by Wedding Venues, Lakes + Fire Pit ✨
10.0 out of 10, Exceptional, (5)
"Cute house and well stocked. We only stayed for 1 night but would stay again if in the area."
✨Chic Retreat by Wedding Venues, Lakes + Fire Pit ✨
Property grounds
Okauchee Lake Vacation Rental w/ Boat Dock!
Okauchee Lake Vacation Rental w/ Boat Dock!
Exterior
Stylish Historic Upper 🌊 Near Lakes, KING Bed + Walk 2 Downtown
10.0 out of 10, Exceptional, (22)
"We really enjoyed our stay! The home is clean and decor is cute. The beds and furniture were very comfortable. The home had everything we needed. The hosts communicated well. We loved walking into town. It’s close to a small beach front lake access. We will come back!"
Stylish Historic Upper 🌊 Near Lakes, KING Bed + Walk 2 Downtown
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See all available properties in Woodland
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 Woodland you may be interested in

Property amenity
Country Inn & Suites by Radisson, West Bend, WI
2.5 star property
8.2 out of 10, Very good, (658)
"Our suite was spacious. The bed was firm. Breakfast was basic but good."
The price is £70
includes taxes & fees
23 Jun - 24 Jun
Country Inn & Suites by Radisson, West Bend, WI
Individually furnished, desk, laptop workspace, blackout curtains
AmericInn by Wyndham West Bend
2.5 star property
8.4 out of 10, Very good, (444)
"Right off the Highway, easy access, very handy. I thought there was a swimming pool but there wasn't. That was the only amenities that was missing. "
The price is £62
includes taxes & fees
30 May - 31 May
AmericInn by Wyndham West Bend
Lobby
AmericInn by Wyndham Waupun
2.5 star property
9.0 out of 10, Wonderful, (311)
"The garbage cans were not changed. "
The price is £103
includes taxes & fees
2 Jun - 3 Jun
AmericInn by Wyndham Waupun
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.

Everything you need to know about Woodland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Woodland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodland holiday rentals we have selected for you start as low as £149 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodland rentals

At Expedia, we put the best Woodland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Woodland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Eclectic Hubertus Home w/ Game Room & Fire Pit!: This holiday home rental outside of Woodland offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a microwave and kitchenware. Make the most of games in this rental home to help you unwind.

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.

Recent reviews of Woodland properties
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