Woodland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Woodland vacation rentals

Exterior
Charming studio apartment - Perfect location for the outdoor explorer

Charming studio apartment - Perfect location for the outdoor explorer

Charming studio apartment - Perfect location for the outdoor explorer
Kewaskum
9.8 out of 10, Exceptional, (8)
"Perfect location friendly accommodating hosts!"
United States
steven s.
The price is ￥23,324
￥48,131 total
includes taxes & fees
Dec 25 - Dec 26
Charming studio apartment - Perfect location for the outdoor explorer
Fridge, microwave, oven, stovetop
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

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

SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf
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 ￥19,671
￥57,610 total
includes taxes & fees
Jan 3 - Jan 4, 2026
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf
Terrace/patio
✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨
Oconomowoc
10.0 out of 10, Exceptional, (20)
"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 ￥31,848
￥75,505 total
includes taxes & fees
Dec 25 - Dec 26
✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨
Fridge, microwave, oven, stovetop
Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.
2.0 star property
Oconomowoc
The price is ￥15,362
￥36,059 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.
Interior
The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!

The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!

The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!
2.0 star property
Beaver Dam
9.8 out of 10, Exceptional, (19)
"A beautiful home in a peaceful setting. Well appointed, everything we needed and more for a stress free relaxing getaway. Thank you Doug for the wonderful experience."
United States
Marjean P.
The price is ￥30,909
￥81,137 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!
Exterior
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

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

Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
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 ￥101,478
￥137,523 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
Interior
Historic, 4-bedroom house in charming Hartford

Historic, 4-bedroom house in charming Hartford

Historic, 4-bedroom house in charming Hartford
2.0 star property
Hartford
The price is ￥92,891
￥139,455 total
includes taxes & fees
Dec 29 - Dec 30
Historic, 4-bedroom house in charming Hartford
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodland Hotel Reviews

Holiday Inn Express & Suites Beaver Dam by IHG

Holiday Inn Express & Suites Beaver Dam by IHG

10/10 Excellent
"Great accommodations, clean, friendly staff, great breakfast "
SARAH 1-night trip
Posted 4 days ago
Holiday Inn Express & Suites Beaver Dam by IHG

Find out more about Woodland

Search for holiday rentals in Woodland on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodland using one of the methods below:

  • View our selection of featured holiday rentals in Woodland
  • Use the map to find apartments and other holiday homes in the Woodland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodland while they last

Look no further and take a look at our great range of rental properties in Woodland!

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?

One-of-a-kind Blue Tree House Retreat • Holy Hill Getaway • Hiking Trails: This vacation home rental outside of Woodland is located on a lake and has a balcony, a garden, 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.