Book Holiday Homes in Portland

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Featured Holiday Homes in Portland

This big old charming house Viroqua

This big old charming house Viroqua

Viroqua
Located in Viroqua, this vacation home is within a 5-minute drive of Fortney Underground Theater and Vernon Memorial Healthcare.
This big old charming house Viroqua
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

Tomah
With a stay at this vacation home, you'll be centrally located in Tomah, within a 15-minute drive of Tomah Health and Area Community Theatre.
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included

Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included

La Crosse
The price is AU$681 per night from 6 Jan to 7 Jan
AU$681
includes taxes & fees
6 Jan - 7 Jan 2025
With a stay at this vacation home in La Crosse (Grandview-Emerson), you'll be steps from University of Wisconsin-La Crosse and 3 minutes by foot from Myrick ...
Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included
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Wisconsin's Driftless Region Retreat

Wisconsin's Driftless Region Retreat

Viroqua
Located in Viroqua, this vacation home is in a rural location, within a 10-minute drive of Viroqua Clinic and Viroqua Country Club.
Wisconsin's Driftless Region Retreat
Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.

Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.

Stoddard
When you stay at this vacation home in Coon Valley, you'll be 13 minutes by car from Shrine of our Lady of Guadalupe.
Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.
Driftless Area Country House: large deck, spring fed creek, Amish area

Driftless Area Country House: large deck, spring fed creek, Amish area

Wilton
Located in Wilton, this vacation home is in a rural location, within a 15-minute drive of Tomah Health and Area Community Theatre.
Driftless Area Country House: large deck, spring fed creek, Amish area
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

La Crosse
The price is AU$407 per night from 5 Jan to 6 Jan
AU$407
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at this vacation home in La Crosse, you'll be a 3-minute walk from Swarthout Museum and 6 minutes by foot from Children's Museum of La Crosse.
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
3-bedroom country home in the driftless.

3-bedroom country home in the driftless.

Westby
Located in Westby, this vacation home is within a 15-minute drive of Vernon Vineyards and Branches Winery.
3-bedroom country home in the driftless.
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

La Crosse
Located in La Crosse, this vacation home is on a river, a 4-minute drive from Mount La Crosse Ski Area and 5 minutes from Shrine of our Lady of Guadalupe.
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities
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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.

Portland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Portland vacation homes are the perfect way for you to wing it.

Holiday houses in Portland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Portland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Portland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Portland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Portland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Portland Holiday Homes essential information

Accommodation
68 Holiday Homes
Lowest Price
AU$113
Highest Price
AU$681
Popular accommodation
This big old charming house Viroqua, Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People., Spacious Dog Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Firewood Included, Wisconsin's Driftless Region Retreat, Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley., Driftless Area Country House: large deck, spring fed creek, Amish area , Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion, 3-bedroom country home in the driftless. , Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

Top trending hotels in Portland

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

2.5 out of 5
3060 S Kinney Coulee Rd, Onalaska, WI
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 29 Dec to 30 Dec
AU$184
includes taxes & fees
29 Dec - 30 Dec
With a stay at Stoney Creek Hotel La Crosse - Onalaska in Onalaska, you'll be in the business district, just a 4-minute walk from Gundersen Lutheran Onalaska ...
Stoney Creek Hotel La Crosse - Onalaska
Stay Suites

Stay Suites

2.5 out of 5
9409 Highway 16, Onalaska, WI
Fully refundableReserve now, pay when you stay
The price is AU$128 per night from 24 Dec to 25 Dec
AU$128
includes taxes & fees
24 Dec - 25 Dec
With a stay at Stay Suites in Onalaska, you'll be a 5-minute walk from Lost Island Wine and 7 minutes by foot from Valley View Mall.
Stay Suites
AmericInn by Wyndham West Salem

AmericInn by Wyndham West Salem

2.5 out of 5
125 Buol Road, West Salem, WI
Fully refundableReserve now, pay when you stay
The price is AU$113 per night from 30 Dec to 31 Dec
AU$113
includes taxes & fees
30 Dec - 31 Dec
Located in West Salem, AmericInn by Wyndham West Salem is within a 5-minute drive of Hamlin Garland House and Marie W. Heider Center for the Arts.
AmericInn by Wyndham West Salem
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Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel

Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel

2.5 out of 5
2614 MIDWEST DRIVE, Onalaska, WI
Fully refundable
The price is AU$162 per night from 5 Jan to 6 Jan
AU$162
includes taxes & fees
5 Jan - 6 Jan 2025
Located in Onalaska, Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel is within a 5-minute drive of Lost Island Wine and Valley View Mall.
Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel
Don't see what you're looking for?
See all available properties in Portland
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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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^Subject to availability and chosen travel dates.