Portland Holiday Rentals

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Holiday Rentals in Portland

Our top choices for Portland holiday rentals

Blakley Hobbit Small Cabin

7.8 out of 10, Good, (45)
"Very nice place. 10/10 would stay again"
The price is AU$189
includes taxes & fees
2 Sept - 3 Sept
Blakley Hobbit Small Cabin

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

9.2 out of 10, Wonderful, (5)
"Nice place across from a campground. "
The price is AU$485
includes taxes & fees
2 Sept - 3 Sept
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

10.0 out of 10, Exceptional, (39)
"House was perfect, clean and cozy! Will definitely book again!"
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

Country Pines Cottage - 1000 SQ/FT in the country - Peaceful & Relaxing

10.0 out of 10, Exceptional, (179)
"This is the third time staying at this very quaint, super clean VRBO. I would highly recommend this well cared for place. "
Country Pines Cottage - 1000 SQ/FT in the country - Peaceful & Relaxing

Blakley Hobbit Large Cabin

8.4 out of 10, Very good, (37)
"We loved this spot and will definitely be booking it again. The cabin has everythinf you need for a quick easy vacation. "
The price is AU$261
includes taxes & fees
2 Sept - 3 Sept
Blakley Hobbit Large Cabin

Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.

10.0 out of 10, Exceptional, (400)
"Had a wonderful stay at the property! "
Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.

Cozy first floor at the heart of downtown Viroqua

10.0 out of 10, Exceptional, (47)
"Great spot right on the edge of downtown"
The price is AU$276
includes taxes & fees
2 Sept - 3 Sept
Cozy first floor at the heart of downtown Viroqua

Jake's Place

9.6 out of 10, Exceptional, (5)
"Was so much better than the large groups of people at motels and quit"
The price is AU$457
includes taxes & fees
2 Sept - 3 Sept
Jake's Place

Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View

9.8 out of 10, Exceptional, (141)
"Great spot for trout fishing and a great place to stay and relax on the porch after a full day exploring the many trout streams."
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View

Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

10.0 out of 10, Exceptional, (233)
"Great place to stay, the area was beautiful and the place was immaculate!"
Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

Riverview Cabin home!

9.6 out of 10, Exceptional, (47)
"Ive been going up to Stoddard for over 20 years what a beautiful house with amazing views."
Riverview Cabin home!

Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

10.0 out of 10, Exceptional, (256)
"We had a wonderful stay. Great hosts and a perfect cabin."
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (34)
"House was amazing and was exactly as advertised. Would definitely stay again."
The price is AU$374
includes taxes & fees
7 Sept - 8 Sept
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Quiet countryside shipping container home. Relax or enjoy outdoor recreation

10.0 out of 10, Exceptional, (74)
"Excellent, will definitely return"
Quiet countryside shipping container home. Relax or enjoy outdoor recreation

Lakeside Ranch Cabin.

8.8 out of 10, Excellent, (75)
"This place is such a beautiful little gem. We needed to get out of Chicago for a few days and this was the perfect spot to do that! I highly recommend! "
Lakeside Ranch Cabin.

Clean Log Cabin in Trout Fishing mecca!!!!

10.0 out of 10, Exceptional, (20)
"Great location to access driftless trout fishing. Plenty of space anc comfort for a larger group."
Clean Log Cabin in Trout Fishing mecca!!!!

Peaceful Country Comfort W Panoramic Views of Big Creek Valley

10.0 out of 10, Exceptional, (134)
"Thank you for hosting another great visit with our family!"
Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

9.8 out of 10, Exceptional, (7)
"Was such a charming property. We were made to feel very welcome. I’d like to go back and stay again."
Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

Place of Peace - the Artist's Refuge

10.0 out of 10, Exceptional, (7)
"What a beautiful location! We went hiking and enjoyed the scenery. Loved the baby cows across the road. Thank you for sharing with us!"
The price is AU$381
includes taxes & fees
6 Sept - 7 Sept
Place of Peace - the Artist's Refuge

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

9.8 out of 10, Exceptional, (40)
"Very nice property that we used for a weekend getaway."
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities
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 Portland Hotel Reviews

Find out more about Portland

Find out more about Portland

Everything you need to know about Portland 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 Portland 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 Portland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland 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 Portland holiday rentals we have selected for you start as low as AU$189 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland 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 Portland 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 Portland 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 Portland. 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 a holiday rental in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, 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 Portland has to offer?

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola: This holiday home rental outside of Portland offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a pool table.

What can I see and do in Portland?

While exploring the area, visit family-friendly sights like Dregne's Scandinavian Gifts, or get outside and enjoy nature at Norskedalen Nature and Heritage Center. Branches Winery and Elroy Sparta State Trail are a couple of places you'll find in the wider area.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for families.