Portland Vacation Rentals

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Vacation Rentals in Portland

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

La Crosse
10.0 out of 10, Exceptional, (41)
"Overall was a great experience. The property manager communication was great. The property was clean and well-kept."
United States
Bill H.
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

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

Powell-Poage-Hamilton
10.0 out of 10, Exceptional, (156)
"Really enjoyed our stay here. Stayed just a couple nights and everything was clean, comfortable and cozy. Location was perfect for our needs. Would highly recommend.."
United States
Mary B.
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples

La Crosse
10.0 out of 10, Exceptional, (109)
"Nice open space for cooking/family time and kids loved playing school/writing on chalk board!"
United States
Sara D.
Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples

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

Westby
10.0 out of 10, Exceptional, (12)
"Was such a charming property. We were made to feel very welcome. I’d like to go back and stay again."
United States
Julie
Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

Blakley Hobbit Small Cabin

Viola
7.8 out of 10, Good, (51)
"Great"
United States
Renee F.
$115 nightly
The price is $121
Nov 22 - Nov 23
Total with taxes and fees
Blakley Hobbit Small Cabin

Blakley Hobbit Large Cabin

Viola
8.2 out of 10, Very Good, (39)
"We loved this spot and will definitely be booking it again. The cabin has everythinf you need for a quick easy vacation. "
United States
Justine C.
$160 nightly
The price is $169
Nov 14 - Nov 15
Total with taxes and fees
Blakley Hobbit Large Cabin

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

Norwalk
9.6 out of 10, Exceptional, (22)
"We had a wonderful time having a family gathering at this beautiful manor in a breathtaking setting! Thanks Paula!"
United States
John G.
$747 nightly
The price is $788
Nov 17 - Nov 18
Total with taxes and fees
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

3BR Ranch / Near Hospitals, Universities, Bluff, River, Coffee Shop, & More!

Holy Trinity-Longfellow
10.0 out of 10, Exceptional, (12)
"Don't hesitate!! Amazing beautiful home with an amazing host. Style , grace , comfortable. If any issues arise rest assured Kim will handle it. She went above and beyond for my family and I will absolutely book with her every visit. If she has others around the world I'd be happy to only use her properties from this point forward if able so I know it would be elegant and homey. You will not regret this stay!!"
United States
Dawn S.
3BR Ranch / Near Hospitals, Universities, Bluff, River, Coffee Shop, & More!

Quaint cabin overlooking the creek below and wetlands in the valley basin.

Norwalk
10.0 out of 10, Exceptional, (17)
"Our cabin was very clean, everything was where it was easy to find. The host was every kind and courteous. "
United States
Christina k.
$278 nightly
The price is $293
Nov 16 - Nov 17
Total with taxes and fees
Quaint cabin overlooking the creek below and wetlands in the valley basin.

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

Stoddard
10.0 out of 10, Exceptional, (407)
"Amazing views and very quiet area"
United States
Shawntelle M.
Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.

Riverview Cabin home!

Stoddard
9.6 out of 10, Exceptional, (50)
"Great Place! Amazing views! The fishing was excellent! We will definitely be back!"
United States
Keith K.
Riverview Cabin home!

Lakeside Ranch Cabin.

Tomah
8.8 out of 10, Excellent, (77)
"Wonderful, private experience."
United States
Molly M.
Lakeside Ranch Cabin.

This big old charming house Viroqua

Viroqua
10.0 out of 10, Exceptional, (34)
"Great house! We had everything we needed and had a great weekend!!"
United States
Kimberly
This big old charming house Viroqua

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

Grandview-Emerson
10.0 out of 10, Exceptional, (49)
"Our stay was absolutely wonderful! It started with the amazing host, Beth! The house might look small from the outside, but, was very comfortable for our family, especially with 3 bedrooms having king-size beds. From start to finish this experience was top-notch!! I highly recommend this VRBO."
United States
Deb U.
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

Place of Peace - the Artist's Refuge

La Farge
10.0 out of 10, Exceptional, (13)
"We had a lovely, peaceful stay here. The house is clean, uncluttered, and open-feeling, and the view outside is beautiful. There were small luxurious touches throughout that made this place feel loved. The location was perfect for river trips on the Kickapoo. "
United States
Catherine W.
$235 nightly
The price is $247
Nov 23 - Nov 24
Total with taxes and fees
Place of Peace - the Artist's Refuge

Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Sparta
10.0 out of 10, Exceptional, (137)
"We very much enjoyed our stay at Larry's and Luann's VRBO apartment. It had everything we needed, was extremely clean and very comfortable. Larry and Luann are great hosts - very responsive and very accommodating. We would highly recommend this property!"
United States
Andrea A.
Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Jake's Place

Powell-Poage-Hamilton
9.8 out of 10, Exceptional, (8)
"Was so much better than the large groups of people at motels and quit"
United States
Jimmy S.
$254 nightly
The price is $292
Nov 16 - Nov 17
Total with taxes and fees
Jake's Place

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

La Crosse
9.8 out of 10, Exceptional, (46)
"Gorgeous place!"
United States
Kevin D.
$209 nightly
The price is $240
Nov 16 - Nov 17
Total with taxes and fees
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

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

Viroqua
10.0 out of 10, Exceptional, (266)
"We had a wonderful stay. Great hosts and a perfect cabin."
United States
Travis H.
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

Relax and watch all the different wildlife pass by as you put life on pause

Norwalk
9.0 out of 10, Wonderful, (2)
"We had the pleasure of getting a little snow during our stay which was awesome.But the roads from the cabin were sloppy with the melt the following day and we had trouble getting out to go for a grocery run. Kirsty and Kyle were very helpful and were kind enough to bring us some coffee and flour. Really great folks and a very beautiful and private location. Great space to reset from reality. Highly recommend."
United States
Nick W.
$294 nightly
The price is $310
Nov 14 - Nov 15
Total with taxes and fees
Relax and watch all the different wildlife pass by as you put life on pause
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 $121 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?

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities: This vacation home rental near Portland is located on a river and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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.