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Portland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Portland vacation rentals

Terrace/patio

1. 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 29 - Aug 30
Total with taxes and fees
Blakley Hobbit Small Cabin
Interior

2. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"Absolutely wonderful as always will be back"
United States
Chad E.
$196 nightly
The price is $207
Aug 31 - Sep 1
Total with taxes and fees
Your adventure begins the second you arrive!
Property grounds

3. #10 Blakley Hobbit Campground-Tent spot

#10 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Huan B.
$40 nightly
The price is $42
Aug 29 - Aug 30
Total with taxes and fees
#10 Blakley Hobbit Campground-Tent spot
Exterior

4. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very Good, (46 reviews)
"A quiet spot w excellent scenery along the Kickapoo River. Great communication w host & easy check-in/out process."
United States
Rebecca B.
$160 nightly
The price is $169
Aug 29 - Aug 30
Total with taxes and fees
Blakley Hobbit Large Cabin
Dining

5. 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.
$356 nightly
The price is $375
Sep 7 - Sep 8
Total with taxes and fees
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
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 30 - Aug 31
Total with taxes and fees
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Living area

7. 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 30 - Aug 31
Total with taxes and fees
Secluded Rustic Cabin
Terrace/patio

8. The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,

The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,
Viroqua
10.0 out of 10, Exceptional, (1 review)
"It's a great little cabin, perfect if you need a place while exploring the creeks around Viroqua. Exceptionally clean, thoughtfully outfitted, very comfortable. The setting is excellent, and the owner Kathi went out of her way to make me feel welcome. Highly recommended."
United States
Christian H.
$133 nightly
The price is $140
Aug 31 - Sep 1
Total with taxes and fees
The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,
Interior

9. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (58 reviews)
"This was my second time staying at the Honey Haven and I would love to stay again. The host does a wonderful job keeping the property in great shape and the area that the property is in is so special."
United States
Eric R.
$240 nightly
The price is $253
Sep 2 - Sep 3
Total with taxes and fees
The Honey Haven
Exterior detail

10. 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)
"It was very clean. Perfectly located in quaint downtown Viroqua."
United States
Rose B.
$160 nightly
The price is $178
Aug 31 - Sep 1
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua
Property grounds

11. 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
Sep 3 - Sep 4
Total with taxes and fees
Peaceful Country Comfort W Panoramic Views of Big Creek Valley
Living area

12. The Hilltop

The Hilltop
Norwalk
9.6 out of 10, Exceptional, (12 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
Sep 8 - Sep 9
Total with taxes and fees
The Hilltop
Property grounds

13. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
$40 nightly
The price is $42
Aug 29 - Aug 30
Total with taxes and fees
#9 Blakley Hobbit Campground-Tent spot
Property grounds

14. #8 Blakley Hobbit Campground-Tent spot

#8 Blakley Hobbit Campground-Tent spot
Viola
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.
$40 nightly
The price is $42
Aug 29 - Aug 30
Total with taxes and fees
#8 Blakley Hobbit Campground-Tent spot
Exterior

15. Country Living at its Finest

Country Living at its Finest
Viroqua
9.8 out of 10, Exceptional, (238 reviews)
"Great cabin -private but close enough to town and near many trout streams."
United States
jennifer g.
$210 nightly
The price is $222
Sep 11 - Sep 12
Total with taxes and fees
Country Living at its Finest
Property grounds

16. 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 29 - Aug 30
Total with taxes and fees
Blakley Hobbit Campground-RV spot #1
Property grounds

17. 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 29 - Aug 30
Total with taxes and fees
Blakley Hobbit Campground-RV spot #4
Property grounds

18. #4 Blakley Hobbit Campground-Tent spot

#4 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (2 reviews)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
$40 nightly
The price is $42
Aug 29 - Aug 30
Total with taxes and fees
#4 Blakley Hobbit Campground-Tent spot
Living area

19. Stylish 1 bedroom cottage along the Mississippi River

Stylish 1 bedroom cottage along the Mississippi River
Stoddard
9.6 out of 10, Exceptional, (32 reviews)
"Perfect for a weekend getaway! Super clean and had everything we needed. "
United States
Dean H.
$155 nightly
The price is $164
Aug 30 - Aug 31
Total with taxes and fees
Stylish 1 bedroom cottage along the Mississippi River
Room

20. 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
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

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

10/10 Excellent
"The property's pretty outdated and beat up.\nIt shows from a minute you walk in the door the staff is very helpful. I enjoyed my stay i did not sleep under the covers because as soon as I opened app the bed, there was something black in the bed. So I j covered"
Michael 1-night trip
Posted less than an hour ago
Stoney Creek Hotel La Crosse - Onalaska

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 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.