Woodland Holiday Rentals

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Holiday Rentals in Woodland

Holiday Home in Richfield

10.0 out of 10, Exceptional, (18)
"Beautiful home with beautiful surroundings. Beautiful home great place to stay."
United States
Melissa H.
NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

Holiday Home in Hartford

10.0 out of 10, Exceptional, (5)
"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. "
United States
Nicole D.
The price is NZ$1,433
includes taxes & fees
10 Dec - 11 Dec
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Holiday Home in Oconomowoc

10.0 out of 10, Exceptional, (3)
"The house was absolutely perfect for our group. The backyard was a great area for our group to get together play yard games and be able to enjoy the lake at the same time. For the few hours of rain we experienced, we were able to enjoy the fun arcade games in the basement to pass our time. Oh and how could I forget the indoor pool!Katie was a wonderful host. Great communication and she was readily available to help us on the property if any requests were asked. She is very knowledgeable about...
United States
Billy L.
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Holiday Home in Juneau

10.0 out of 10, Exceptional, (43)
"Wonderful place for our families and 8 children age ranges 2-10. Very kind house who understood the chaos. Many water toys to explore the water and life jackets, beach towels and even sunscreen. Thank you so much for a pleasant stay and for being kind. "
United States
Jennifer M.
4 Bdrm 4 Bath Lake front Lake Sinissippi home

Holiday Home in Rubicon

9.6 out of 10, Exceptional, (4)
"This place was absolutely amazing! It’s cozy and filled with things to do! I absolutely recommend and would stay here again. "
United States
Maylee K.
Erin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!

Holiday Home in Hubertus

9.6 out of 10, Exceptional, (166)
"Very comfortable and spacious for 12 people. Excellent location for nearby restaurants and park facilities. Definitely recommend for a stay, and loved how big the kitchen was! "
United States
Elaine D.
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Holiday Home in Hustisford

9.6 out of 10, Exceptional, (189)
"The house was so nice And very clean Communication with the owner was excellent Nice quiet place to relax "
United States
Heidi H.
Beautiful lakefront, Newly Remodeled Lower Level!

Holiday Home in Oconomowoc

10.0 out of 10, Exceptional, (5)
"We really liked our stay here. The property was fantastic and the house is wonderful. We played bocce outside and multiple neighbors stopped and had lovely chats with us!"
United States
Donny S.
Spacious Modern Build, 4 BD/4 BA, Near Downtown and Hwy

Holiday Home in Okauchee Lake

9.8 out of 10, Exceptional, (7)
"The lake view is gorgeous; the accommodations spacious; and the opportunities for a good time endless!"
United States
Chrisanne W.
Okauchee Lake Home: 4BR/4BA | Hot Tub | Central to town and wedding venues

Holiday Home in Oconomowoc

10.0 out of 10, Exceptional, (17)
"Clean, cozy and convenient for walks dowtown! Stayed a week- Loved all of the special touches- including lots of towels, keurig pods and the smores basket! Thank you for a liovely stay in Oconomowoc."
United States
sk k.
The price is NZ$907
includes taxes & fees
21 Dec - 22 Dec
✨ Stylish Home with Fire Pit- Near Downtown & Weddings Venues ✨

Holiday Home in Campbellsport

10.0 out of 10, Exceptional, (41)
"This was by far the most unique setting of any we have enjoyed! So much care and thought was put into the decor. Anything a person might have needed for food prep or personal care was provided. The downstairs bed, where we slept, was so comfy. "
United States
Richard C.
The price is NZ$355
includes taxes & fees
22 Nov - 23 Nov
Gleason's Chouse

Holiday Home in Hartford

9.8 out of 10, Exceptional, (10)
"Very welcoming and beautiful property. We loved being right on the lake. Nicely decorated and the kitchen was well stocked.Allie & Ljilijana were easy to work with and great hosts.Would highly recommend this property."
United States
Nikki A.
Charming 2-bedroom Lake House

Apartment in Kewaskum

10.0 out of 10, Exceptional, (40)
"We very much enjoyed our stay in a bucolic setting."
United States
Colin B.
3 miles from Sunburst Ski Hill. Close to great hikiing and snow mobile trails

Holiday Home in West Bend

10.0 out of 10, Exceptional, (46)
"What great property! Stayed here for our annual golf trip and this place has everything you need. The back yard and patio was our go to hangout spot. If we are back in the area again this is the place we will rent again. "
United States
Nate W.
Private estate with tennis court and more

Holiday Home in Beaver Dam

9.6 out of 10, Exceptional, (13)
"The house is beautifully remodeled. Up-to-date kitchen, modern appliances, which was important to us as we like to cook and share family meals. Comfortable bedrooms, lots of space for storage. Nice patio area with great view of lake, especially at sunset. Our family enjoyed our stay."
United States
Judy D.
Lakefront house! SUP and Kayak use included. Near golf!

Cabin in Campbellsport

9.8 out of 10, Exceptional, (11)
"Very beautiful place. "
United States
Jason W.
Cozy Treehouse on the Lake

Holiday Home in Ixonia

9.6 out of 10, Exceptional, (4)
"Clean place. "
United States
John M.
The price is NZ$432
includes taxes & fees
8 Dec - 9 Dec
Relax & Reboot in this Charming 2-Bedroom Townhome

Apartment in Hartford

10.0 out of 10, Exceptional, (4)
"Gorgeous interior, responsive host, clear instructions. Enjoyed proximity to hiking, cafe, and arcade. "
United States
M. M.
The price is NZ$652
includes taxes & fees
21 Nov - 22 Nov
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

Cottage in Maplewood

3.0 star property
Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!

Cabin in Richfield

10.0 out of 10, Exceptional, (2)
"Definitely recommend for a small group (perfect for a couple). Feels like a treehouse, but has nice amenities and everything you need, plus a comfy bed! "
United States
Melissa B.
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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Top Woodland Hotel Reviews

Find out more about Woodland

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, 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 NZ$355 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?

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby: This holiday home rental outside of Woodland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 Sleeping Dragon Ranch, 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.