Portland Vacation Rentals

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Our top choices for Portland vacation rentals

10.0 out of 10, Exceptional, (1)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
$70 nightly
The price is $74
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Campground-RV spot #4

Vacation Home in Westby

The Honey Haven
10.0 out of 10, Exceptional, (46)
"Wonderful! Beautiful, serene place, clean environment, perfect!"
United States
Karen S.
$228 nightly
The price is $241
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Honey Haven

Vacation Home in La Farge

Place of Peace - the Artist's Refuge
9.8 out of 10, Exceptional, (17)
"Great location. Near a super apple orchard (J and R Country Ridge Orchard). Beautiful area, quiet evenings and peaceful mornings! "
United States
Kirk M.
$234 nightly
The price is $246
Jan 2 - Jan 3, 2026
Total with taxes and fees
Place of Peace - the Artist's Refuge
10.0 out of 10, Exceptional, (52)
"Great convenience, quiet, well maintained, cute & cozy! Would definitely stay again! "
United States
Lynette W.
$160 nightly
The price is $178
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua
10.0 out of 10, Exceptional, (22)
"Beautiful cabin 100% recommend good communication "
Mexico
anayeli
$278 nightly
The price is $293
Jan 4 - Jan 5, 2026
Total with taxes and fees
Quaint cabin overlooking the creek below and wetlands in the valley basin.
9.6 out of 10, Exceptional, (8)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
$297 nightly
The price is $313
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
10.0 out of 10, Exceptional, (3)
"Easy check in. Beautiful cabin. We will be back for sure!"
United States
Dana S. S.
$322 nightly
The price is $340
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ready to become a real love bird? Beautiful cabin to wake up hearing song birds
$145 nightly
The price is $153
Jan 5 - Jan 6, 2026
Total with taxes and fees
Farm Stay, convenient yet quiet - complete with cows in the backyard!

Vacation Home in Powell-Poage-Hamilton

Jake's Place
9.8 out of 10, Exceptional, (8)
"Great place, great location. Very clean & practical! "
United States
Cori C.
$285 nightly
The price is $328
Jan 4 - Jan 5, 2026
Total with taxes and fees
Jake's Place
10.0 out of 10, Exceptional, (1)
$40 nightly
The price is $42
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #9

Apartment in Holy Trinity-Longfellow

Hidden Gem - 1BR/1Bath in Lax WI
9.6 out of 10, Exceptional, (15)
"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
$144 nightly
The price is $166
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hidden Gem - 1BR/1Bath in Lax WI
9.6 out of 10, Exceptional, (22)
"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.
$669 nightly
The price is $706
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
10.0 out of 10, Exceptional, (2)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
$40 nightly
The price is $42
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #4
$40 nightly
The price is $42
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #3
10.0 out of 10, Exceptional, (3)
"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.
$40 nightly
The price is $42
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #10
2.0 star property
6.0 out of 10, (1)
"Pros: Good Host, great value and location, pet friendly, cleanCons: Listing said entire home, so did not realize host would be on the property. Listing should have mentioned kids that are very loud during our stay. Understandable with kids, but note should have been made as two people were unable to sleep. Not much room for parking with host’s vehicles. More clarity and details on the listing would significantly help."
United States
Dylan M.
$135 nightly
The price is $142
Jan 5 - Jan 6, 2026
Total with taxes and fees
Large home space minutes from La Crosse
9.0 out of 10, Wonderful, (2)
"We enjoyed the campground very much. A little lacking in facilities but location makes up for it in spades!"
United States
Nicholas B.
$40 nightly
The price is $42
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Campground-Tent spot #8
9.0 out of 10, Wonderful, (2)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
$70 nightly
The price is $74
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blakley Hobbit Campground-RV spot #1

Vacation Home in Cashton

Secluded Rustic Cabin
9.8 out of 10, Exceptional, (54)
"So relaxing and an amazing house"
United States
Ann W.
$466 nightly
The price is $491
Jan 3 - Jan 4, 2026
Total with taxes and fees
Secluded Rustic Cabin
2.0 star property
9.0 out of 10, Wonderful, (2)
"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.
$398 nightly
The price is $419
Jan 16 - Jan 17, 2026
Total with taxes and fees
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $242 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland vacation 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 vacation.

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 vacation rental in Portland?

Yes, you can find vacation rentals near top sights in Portland, or you can choose a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Portland?

Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.: This vacation home rental near Portland is located in a rural location and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so 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 larger area.

What are vacation rentals like in Portland?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Portland. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.