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Portland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Portland vacation rentals

Living area

1. Secluded Rustic Cabin

Secluded Rustic Cabin
Cashton
9.8 out of 10, Exceptional, (58 reviews)
"What a wonderful property! "
United States
Becky K.
$478 nightly
The price is $504
Aug 23 - Aug 24
Total with taxes and fees
Secluded Rustic Cabin
Interior

2. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely wonderful as always will be back"
United States
Chad E.
$220 nightly
The price is $232
Aug 26 - Aug 27
Total with taxes and fees
Your adventure begins the second you arrive!
Dining

3. Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Cashton
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.
$358 nightly
The price is $377
Aug 24 - Aug 25
Total with taxes and fees
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Interior

4. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (57 reviews)
"Great place. Perfect location for the Driftless. The host were terrific."
United States
John I.
$240 nightly
The price is $253
Aug 28 - Aug 29
Total with taxes and fees
The Honey Haven
Living area

5. The Incline

The Incline
Norwalk
10.0 out of 10, Exceptional, (6 reviews)
"This place is a perfect couples getaway! "
United States
Kurt T.
$343 nightly
The price is $362
Aug 23 - Aug 24
Total with taxes and fees
The Incline
Exterior

6. Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Ontario
10.0 out of 10, Exceptional, (6 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
$172 nightly
The price is $181
Aug 31 - Sep 1
Total with taxes and fees
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Terrace/patio

7. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (56 reviews)
"fishing cabin."
United States
joe
$115 nightly
The price is $121
Aug 24 - Aug 25
Total with taxes and fees
Blakley Hobbit Small Cabin
Exterior detail

8. Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
9.8 out of 10, Exceptional, (59 reviews)
"Nice place to stay right in town perfect for a couple "
United States
Pete G.
$160 nightly
The price is $178
Aug 24 - Aug 25
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua
Exterior

9. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very Good, (46 reviews)
"Very peaceful, charming rustic cabin. I highly recommend and we plan to come back. "
United States
Jonathan C.
$160 nightly
The price is $169
Aug 23 - Aug 24
Total with taxes and fees
Blakley Hobbit Large Cabin
Property grounds

10. Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Peaceful Country Comfort W Panoramic Views of Big Creek Valley
Sparta
10.0 out of 10, Exceptional, (154 reviews)
"It was all amazing! Great hosts! Beautiful home! "
United States
Aliyah C.
$174 nightly
The price is $184
Aug 30 - Aug 31
Total with taxes and fees
Peaceful Country Comfort W Panoramic Views of Big Creek Valley
Living area

11. The Hilltop

The Hilltop
Norwalk
10.0 out of 10, Exceptional, (11 reviews)
"Clean, well supplied, had everything we needed. Basic cooking utensils were there, very comfortable, water was great, AC worked well, very cozy!"
United States
Anatole W.
$343 nightly
The price is $362
Aug 25 - Aug 26
Total with taxes and fees
The Hilltop
Exterior

12. Country Living at its Finest

Country Living at its Finest
Viroqua
9.8 out of 10, Exceptional, (235 reviews)
"Great cabin -private but close enough to town and near many trout streams."
United States
jennifer g.
$211 nightly
The price is $223
Sep 11 - Sep 12
Total with taxes and fees
Country Living at its Finest
Property grounds

13. Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (1 review)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
$70 nightly
The price is $74
Aug 21 - Aug 22
Total with taxes and fees
Blakley Hobbit Campground-RV spot #4
Living area

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

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.0 out of 10, Wonderful, (15 reviews)
"Nice place"
United States
Thomas G.
$297 nightly
The price is $313
Aug 21 - Aug 22
Total with taxes and fees
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Living area

15. The Hideaway

The Hideaway
Norwalk
9.0 out of 10, Wonderful, (2 reviews)
"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.
$372 nightly
The price is $392
Aug 23 - Aug 24
Total with taxes and fees
The Hideaway
Room

16. Hidden Gem - 1BR/1Bath in Lax WI

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (17 reviews)
"Lovely property in a great area. Would absolutely stay here again!"
United States
Karen H.
$144 nightly
The price is $166
Sep 17 - Sep 18
Total with taxes and fees
Hidden Gem - 1BR/1Bath in Lax WI
Outdoor dining

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

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Norwalk
9.4 out of 10, Exceptional, (30 reviews)
"Everyone had a great time!"
United States
Jim K.
$679 nightly
The price is $716
Sep 15 - Sep 16
Total with taxes and fees
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Exterior

18. Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
9.8 out of 10, Exceptional, (10 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
$316 nightly
The price is $333
Aug 25 - Aug 26
Total with taxes and fees
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Interior

19. Breezy 4BR | Steps to UW Campus

Breezy 4BR | Steps to UW Campus
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (41 reviews)
"Walkable to grocery store, gas station and Restraunts which was super helpful since the rental car company was closed when we arrived at the airport due to our flight being delayed.Would definitely stay again"
United States
Kim M.
$380 nightly
The price is $437
Sep 1 - Sep 2
Total with taxes and fees
Breezy 4BR | Steps to UW Campus
Property grounds

20. Blakley Hobbit Campground-RV spot #1

Blakley Hobbit Campground-RV spot #1
Viola
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.
$70 nightly
The price is $74
Aug 22 - Aug 23
Total with taxes and fees
Blakley Hobbit Campground-RV spot #1
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

Microtel Inn by Wyndham Onalaska/La Crosse

Microtel Inn by Wyndham Onalaska/La Crosse

10/10 Excellent
"Nice place and breakfast"
Ariana 1-night trip
Posted 1 hour ago
Microtel Inn by Wyndham Onalaska/La Crosse

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.

Explore a world of travel with Expedia

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?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This vacation home rental near 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 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 Elroy Sparta State Trail. LaCrosse River Trail and La Crosse Fairgrounds Speedway 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.