Holiday Rentals in Portland

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Our top choices for Portland holiday rentals

10.0 out of 10, Exceptional, (1 review)
The price is €40
includes taxes & fees
12 Jan - 13 Jan
Blakley Hobbit Campground-Tent spot #9

Holiday Home in Westby

The Honey Haven
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful! Beautiful, serene place, clean environment, perfect!"
United States
Karen S.
The price is €222
includes taxes & fees
12 Jan - 13 Jan
The Honey Haven
10.0 out of 10, Exceptional, (52 reviews)
"Wonderful place! Clean, full of amenities, within walking distance to everything downtown has to offer."
United States
Alina L.
The price is €157
includes taxes & fees
12 Jan - 13 Jan
Cozy first floor at the heart of downtown Viroqua
9.8 out of 10, Exceptional, (17 reviews)
"Great location. Near a super apple orchard (J and R Country Ridge Orchard). Beautiful area, quiet evenings and peaceful mornings! "
United States
Kirk M.
The price is €217
includes taxes & fees
12 Jan - 13 Jan
Place of Peace - the Artist's Refuge
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is €277
includes taxes & fees
12 Jan - 13 Jan
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Apartment in Holy Trinity-Longfellow

Hidden Gem - 1BR/1Bath in Lax WI
9.6 out of 10, Exceptional, (15 reviews)
"A lovely, spacious, clean apartment above a yummy restaurant in a quiet residential neighborhood. We stayed there when we were in town for a 6-hour race in Goose Island State Park, and it was perfect! "
United States
Amy
The price is €146
includes taxes & fees
12 Jan - 13 Jan
Hidden Gem - 1BR/1Bath in Lax WI
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful relaxing getaway!"
United States
Amanda M.
The price is €253
includes taxes & fees
19 Jan - 20 Jan
Quaint cabin overlooking the creek below and wetlands in the valley basin.
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in. Beautiful cabin. We will be back for sure!"
United States
Dana S. S.
The price is €306
includes taxes & fees
12 Jan - 13 Jan
Ready to become a real love bird? Beautiful cabin to wake up hearing song birds
The price is €137
includes taxes & fees
12 Jan - 13 Jan
Farm Stay, convenient yet quiet - complete with cows in the backyard!

Holiday Home in Powell-Poage-Hamilton

Jake's Place
9.8 out of 10, Exceptional, (8 reviews)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is €287
includes taxes & fees
12 Jan - 13 Jan
Jake's Place
10.0 out of 10, Exceptional, (2 reviews)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
The price is €40
includes taxes & fees
12 Jan - 13 Jan
Blakley Hobbit Campground-Tent spot #4
10.0 out of 10, Exceptional, (3 reviews)
"The tent sites are right along the river. Not all of them have a fire pit, picnic table or grill but this is a lovely quiet serene spot to camp. "
United States
Deborah S.
The price is €40
includes taxes & fees
12 Jan - 13 Jan
Blakley Hobbit Campground-Tent spot #10
The price is €40
includes taxes & fees
10 Feb - 11 Feb
Blakley Hobbit Campground-Tent spot #3
10.0 out of 10, Exceptional, (1 review)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
The price is €67
includes taxes & fees
12 Jan - 13 Jan
Blakley Hobbit Campground-RV spot #4
9.6 out of 10, Exceptional, (22 reviews)
"Twelve guys on our annual motorcycle trip. Excellent facilities, beautiful setting, and great riding in the area. Awesome porch with a gas grill and plenty of chairs. We were all impressed with this property and would absolutely book it again in the future."
United States
Jerry K.
The price is €629
includes taxes & fees
14 Jan - 15 Jan
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
9.0 out of 10, Wonderful, (2 reviews)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is €67
includes taxes & fees
10 Feb - 11 Feb
Blakley Hobbit Campground-RV spot #1

Holiday Home in Cashton

Secluded Rustic Cabin
9.8 out of 10, Exceptional, (54 reviews)
"So relaxing and an amazing house"
United States
Ann W.
The price is €432
includes taxes & fees
12 Jan - 13 Jan
Secluded Rustic Cabin
9.0 out of 10, Wonderful, (2 reviews)
"Was in town for a wedding, it was a comfortable place. The master bedroom bed was comfortable and everything was very clean."
United States
Catherine T.
The price is €370
includes taxes & fees
18 Jan - 19 Jan
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
9.0 out of 10, Wonderful, (2 reviews)
"We enjoyed the campground very much. A little lacking in facilities but location makes up for it in spades!"
United States
Nicholas B.
The price is €40
includes taxes & fees
12 Jan - 13 Jan
Blakley Hobbit Campground-Tent spot #8
The price is €40
includes taxes & fees
12 Jan - 13 Jan
Blakley Hobbit Campground-Tent spot #7
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

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 €233 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?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This holiday home rental outside of Portland offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.