Portland Holiday Rentals from €108: Search Short-Term Rentals

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Holiday Rentals in Portland

Escape to a serene cabin surrounded by lush greenery, featuring a cozy porch with a picnic table and bench.

"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."

Cozy cabin nestled among the trees, offering a peaceful retreat with a wooden deck and a small window.

"Easiest check-in, perfectly met expectations and needs."

includes taxes & fees

8 Aug - 9 Aug

Relax in a serene setting with expansive forest views from large windows, accompanied by a comfortable seating area with two armchairs and a small table.

"Great stay. Clean and comfortable. Would stay again."

Cozy cabin-style room with a dining area, sofa, and small kitchen.

"We stayed in Brian’s cabin for a family reunion in La Farge and had a wonderful stay. The cabin was spacious, cozy, clean, and tidy. Brian was also very friendly and helpful when he stopped by to welcome us and tell us all about the area. Lastly, I loved all the beds in the cabin - plenty of room for our big crew to sleep comfortably and soundly. Would love to come back soon."

Escape to a serene cabin surrounded by lush greenery and a majestic tree.

"We had a wonderful stay. Great hosts and a perfect cabin."

Stunning Victorian-style building with a charming front porch and beautifully manicured lawn.

"House was amazing and was exactly as advertised. Would definitely stay again."

includes taxes & fees

13 Aug - 14 Aug

Cozy cabin-style accommodation with a fully equipped kitchen, dining area, and bar.

"We loved this spot and will definitely be booking it again. The cabin has everythinf you need for a quick easy vacation. "

includes taxes & fees

31 Aug - 1 Sept

Enjoy meals in this cozy dining area with a long table and comfortable seating.

"We biked the Elroy Sparta Bike trail. Great location for that in an absolute beautiful location! Very clean and 2 nice bathrooms. Would stay again for sure!"

Enjoy a peaceful retreat with a scenic view from this serene property, featuring a spacious deck and beautifully maintained lawn.

"Wonderful accommodations. My husband and I stayed. Quiet, beautiful views, and close to Hillsboro. Well stocked kitchen, full size appliances, and the bath is beautiful. "

includes taxes & fees

7 Sept - 8 Sept

Relax on the riverside deck with a view of the calm water, surrounded by trees and a distant building.

"We enjoyed our stay at this spacious cabin overlooking a peaceful pond. While the water isn’t swimmable, it was still lovely to look at from the large deck, which was one of the highlights of the property. The hot tub was a nice touch, and the air conditioning worked well, keeping the home comfortable during our stay. The layout features one bedroom and bathroom on the upper level, with additional bedrooms downstairs. Be aware that this cabin is not handicap accessible. It has a metal spiral...

Stunning home with a front porch and a charming entrance.

"Enjoyed our stay. House worked out great- the number of beds/bedrooms and having 2 bathrooms was wonderful. Close to the downtown- easy 30 minute walk."

Standalone cabin surrounded by a lush lawn and two large trees, offering a retreat.

"Loved the place! Clean, cozy and comfortable. Will absolutely stay again if in the area. "

Enjoy a game of pool or relax in the seating area.

"Quiet Place"

includes taxes & fees

2 Sept - 3 Sept

"Nice quiet place to stay, WIFI would be Nic as there in no cell service."

Relax in this spacious living room with a high ceiling and large windows offering a view of the surrounding landscape.

"Had a wonderful stay at the property! "

Rows of grapevines thrive under a trellis system, surrounded by a fence and lush green grass.

"Great place for a weekend getaway!"

Enjoy cooking in this kitchen with a central island, gas stove, refrigerator, and microwave.

"Was so much better than the large groups of people at motels and quit"

includes taxes & fees

11 Aug - 12 Aug

Relax on the lakeside deck with comfortable seating and dining areas.

"2nd time staying at Birch Lake. It is so beautiful and peaceful. Great spot for a girl's weekend!"

Stunning two-story home with a balcony and garage entrance, set amidst a beautifully manicured lawn and lush trees.

"Very nice property that we used for a weekend getaway."

Relax on the lakeside deck with comfortable seating and a tranquil atmosphere.

"This is our second time staying here. It had everything we needed for our group and plenty of space to spread out. Showering took some time as the water pressure was not good in any of the bathrooms, but we managed."

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Top Portland Hotel Reviews

Stoney Creek Hotel La Crosse - Onalaska

10/10 Excellent

"We had a Themed Room and it was nice and big and even had a balcony to sit outside! We loved it!"

Hampton Inn Lacrosse/Onalaska

10/10 Excellent

"I enjoyed the accommodations very well, room was nice, grounds were well kept. I actually left some clothes behind and realized it 2 hours later while traveling back to Georgia. I called the hotel, told them what I'd done and they gathered the stuff up and shipped it to me. Very grateful. "

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, apart-hotels, 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 favorite 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 depends 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 €108 per night. Entering your travel dates in the search wizard you might find 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?

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!: This holiday home rental outside of Portland offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.

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Holiday Rentals in Portland

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Holiday Rentals in Portland

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

Blakley Hobbit Small Cabin

Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

Cozy Amish built cabin in the heart of the Kickapoo Valley Reserve State Park.

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

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Blakley Hobbit Large Cabin

Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Place of Peace - the Artist's Refuge

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

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Cozy Newly Built Cabin with Scenic Views

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

Tranquil Amish-built cabin near Wildcat State Park

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

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

Jake's Place

Lakeside cabin with Hot Tub and full kitchen! Sleeps up to 12 people.

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

Birch Lake Secluded Getaway- Serenity home 5 bedroom sleeps up to 14

Top Portland Hotel Reviews

Stoney Creek Hotel La Crosse - Onalaska

AmericInn by Wyndham Viroqua

Baymont by Wyndham La Crosse/Onalaska

Holiday Inn Express & Suites Onalaska La Crosse Area by IHG

Country Inn & Suites by Radisson, Sparta, WI

Welch Motel

Spark by Hilton La Crosse Onalaska

Hampton Inn Lacrosse/Onalaska

AmericInn by Wyndham West Salem

Find out more about Portland

Frequently asked questions