Portland Vacation Rentals

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Our top choices for Portland vacation rentals

10.0 out of 10, Exceptional, (24 reviews)
"Beautiful relaxing getaway!"
United States
Amanda M.
The price is CA $331
CA $399 total
includes taxes & fees
Mar 3 - Mar 4
Your adventure begins the second you arrive!

Vacation Home in La Farge

Place of Peace - the Artist's Refuge
9.8 out of 10, Exceptional, (17 reviews)
"Easy in and out, the house had everything we needed, and the view was amazing!"
United States
shoua x.
The price is CA $178
CA $337 total
includes taxes & fees
Mar 3 - Mar 4
Place of Peace - the Artist's Refuge
8.0 out of 10, Very good, (40 reviews)
"House was exactly as described. Easy to find. Fun for the kids!"
United States
Emily K.
The price is CA $123
CA $230 total
includes taxes & fees
Mar 15 - Mar 16
Blakley Hobbit Large Cabin

Apartment in Viola

Blakley Hobbit Small Cabin
7.8 out of 10, Good, (51 reviews)
"Enjoy our stay."
United States
Sondra M.
The price is CA $89
CA $165 total
includes taxes & fees
Mar 15 - Mar 16
Blakley Hobbit Small Cabin

Vacation Home in Westby

The Honey Haven
10.0 out of 10, Exceptional, (47 reviews)
"Quiet, clean, nestled in nature!"
United States
jim g.
The price is CA $218
CA $345 total
includes taxes & fees
Mar 25 - Mar 26
The Honey Haven
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is CA $246
CA $426 total
includes taxes & fees
Mar 3 - Mar 4
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
9.6 out of 10, Exceptional, (26 reviews)
"Very clean and well appointed. We enjoyed the convenient location to La Crosse and the many area hiking opportunities. It is on the highway and the railroad is right next to that, just so you know. It didn't bother us much, but we weren't there during the day much either."
United States
Michelle S.
The price is CA $120
CA $155 total
includes taxes & fees
Mar 3 - Mar 4
Stylish 1 bedroom cottage along the Mississippi River

Cabin in Viroqua

Wagonwheel Ranch
9.8 out of 10, Exceptional, (18 reviews)
"Quiet location nice setting. Great host "
United States
Josh K.
The price is CA $381
CA $702 total
includes taxes & fees
Mar 3 - Mar 4
Wagonwheel Ranch
10.0 out of 10, Exceptional, (54 reviews)
"Wonderful place! Clean, full of amenities, within walking distance to everything downtown has to offer."
United States
Alina L.
The price is CA $130
CA $243 total
includes taxes & fees
Apr 1 - Apr 2
Cozy first floor at the heart of downtown Viroqua

Apartment in Holy Trinity-Longfellow

Hidden Gem - 1BR/1Bath in Lax WI
9.6 out of 10, Exceptional, (16 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 CA $149
CA $226 total
includes taxes & fees
Mar 6 - Mar 7
Hidden Gem - 1BR/1Bath in Lax WI

Vacation 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 CA $205
CA $447 total
includes taxes & fees
Mar 8 - Mar 9
Jake's Place

Vacation Home in Holy Trinity-Longfellow

4 BR w/ Bluff Views | Snow-Dusted Escape
9.4 out of 10, Exceptional, (33 reviews)
"Our stay was very nice. Tina was excellent in responding to a few of our needs. Lovey home and nicely decorated."
United States
Mary B.
The price is CA $175
CA $581 total
includes taxes & fees
Mar 8 - Mar 9
4 BR w/ Bluff Views | Snow-Dusted Escape
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 CA $68
CA $101 total
includes taxes & fees
Mar 3 - Mar 4
Blakley Hobbit Campground-RV spot #1
10.0 out of 10, Exceptional, (10 reviews)
"Great place to stay and explore the region. King bed was super comfy and the hot tub so relaxing. House was clean and very spacious- we loved it!"
United States
Kelly H.
The price is CA $326
CA $391 total
includes taxes & fees
Mar 4 - Mar 5
Valley Lodge w/Hot Tub & Arcade.

Vacation Home in Historic Downtown La Crosse

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
9.8 out of 10, Exceptional, (55 reviews)
"Loved the home! Perfect girls weekend!"
United States
Helen H.
The price is CA $252
CA $327 total
includes taxes & fees
Mar 3 - Mar 4
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
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 CA $338
CA $569 total
includes taxes & fees
Mar 14 - Mar 15
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

Vacation Home in Viroqua

Garden Ridge Retreat- Farm Stay
10.0 out of 10, Exceptional, (8 reviews)
"Really enjoyed our stay. Great hosts no issues at all. Amazing views would definitely visit again "
United States
Joseph M.
The price is CA $265
CA $616 total
includes taxes & fees
Mar 4 - Mar 5
Garden Ridge Retreat- Farm Stay
10.0 out of 10, Exceptional, (5 reviews)
"Easy check in. Beautiful cabin. We will be back for sure!"
United States
Dana S. S.
The price is CA $393
CA $472 total
includes taxes & fees
Mar 3 - Mar 4
Your adventure begins the second you arrive!

Vacation Home in Cashton

Secluded Rustic Cabin
9.8 out of 10, Exceptional, (55 reviews)
"So relaxing and an amazing house"
United States
Ann W.
The price is CA $399
CA $667 total
includes taxes & fees
Mar 3 - Mar 4
Secluded Rustic Cabin
9.6 out of 10, Exceptional, (23 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 CA $465
CA $971 total
includes taxes & fees
Mar 5 - Mar 6
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples: This vacation home rental near Portland is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind.

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. Elroy Sparta State Trail and LaCrosse River 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.