Woodland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Woodland

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

Vacation 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.
$721 nightly
The price is $811
Dec 10 - Dec 11
Total with taxes and fees
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
Dining
One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails

Vacation Home in Richfield

10.0 out of 10, Exceptional, (19)
"Beautiful home with beautiful surroundings. Beautiful home great place to stay."
United States
Melissa H.
One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails
Terrace/patio
✨ Stylish Home with Fire Pit- Near Downtown & Weddings Venues ✨

Vacation 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.
✨ Stylish Home with Fire Pit- Near Downtown & Weddings Venues ✨
Outdoor dining
4 Bdrm 4 Bath Lake front Lake Sinissippi home

Vacation Home in Juneau

10.0 out of 10, Exceptional, (43)
"Great property. Lots to do at the house. Plenty of space. "
United States
Justin R.
4 Bdrm 4 Bath Lake front Lake Sinissippi home
Terrace/patio
Erin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!

Vacation 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!
Dining
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Vacation 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
3 bedrooms, in-room safe, free WiFi, bed sheets
Beautiful lakefront, Newly Remodeled Lower Level!

Vacation Home in Hustisford

9.6 out of 10, Exceptional, (190)
"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!
Marina
Charming 2-bedroom Lake House

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

Vacation 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!
Interior
Gleason's Chouse

Vacation 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.
Gleason's Chouse
Exterior
Greenstone Cottage

Vacation Home in Oconomowoc

10.0 out of 10, Exceptional, (28)
"Our family stayed for a lovely weekend at Greenstone cottage. The house was charming, the yard was relaxing, and the rooms were comfortable. "
United States
Jessica G.
Greenstone Cottage
Property grounds
3 miles from Sunburst Ski Hill. Close to great hikiing and snow mobile trails

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
Dining
Spacious Modern Build, 4 BD/4 BA, Near Downtown and Hwy

Vacation 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
Outdoor dining
Private estate with tennis court and more

Vacation Home in West Bend

10.0 out of 10, Exceptional, (46)
"This home is wonderful for family vacations. "
United States
Sarah L.
Private estate with tennis court and more
Interior
Lakefront house! SUP and Kayak use included. Near golf!

Vacation 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!
Property grounds
Cozy Treehouse on the Lake

Cabin in Campbellsport

9.8 out of 10, Exceptional, (13)
"Very beautiful place. "
United States
Jason W.
Cozy Treehouse on the Lake
Microwave, oven, stovetop
Relax & Reboot in this Charming 2-Bedroom Townhome

Vacation Home in Ixonia

9.6 out of 10, Exceptional, (4)
"Clean place. "
United States
John M.
$233 nightly
The price is $246
Dec 1 - Dec 2
Total with taxes and fees
Relax & Reboot in this Charming 2-Bedroom Townhome
Cottage (2 Bedrooms) | Interior
Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!

Cottage in Maplewood

3.0 star property
Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!
Fridge, microwave, oven, stovetop
Okauchee Lake Home: 4BR/4BA | Hot Tub | Central to town and wedding venues

Vacation 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
Fridge, microwave, oven, stovetop
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

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.
$344 nightly
The price is $387
Dec 19 - Dec 20
Total with taxes and fees
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf
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

Quality Inn & Suites

Quality Inn & Suites

10/10 Excellent
"Very clean and neat. Breakfast was presented well and in a clean environment. We would stay here again."
Timothy 1-night trip
Posted 3 days ago
Quality Inn & Suites

Find out more about Woodland

Everything you need to know about Woodland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Woodland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $246 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodland rentals

At Expedia, we put the best Woodland vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Woodland?

Yes, there are vacation rentals close to top sights in Woodland, or you can select a more secluded option if you're looking for relaxation.

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

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby: This vacation home rental outside of Woodland is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection 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 Little Switzerland are a couple of places you'll find in the larger area.

What are vacation rentals like in Woodland?

Vacation rentals are private properties you can book for several days or longer in Woodland. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for family trips or small group gatherings.