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Portland Vacation Rentals

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Our top choices for Portland vacation rentals

1. 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.
The price is CA $281
CA $339 total
includes taxes & fees
Sep 15 - Sep 16
Your adventure begins the second you arrive!

2. Secluded Rustic Cabin

Secluded Rustic Cabin
Cashton
9.8 out of 10, Exceptional, (58 reviews)
"What a wonderful property! "
United States
Becky K.
The price is CA $405
CA $694 total
includes taxes & fees
Sep 7 - Sep 8
Secluded Rustic Cabin

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.
The price is CA $294
CA $519 total
includes taxes & fees
Sep 7 - Sep 8
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

4. 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.
The price is CA $173
CA $250 total
includes taxes & fees
Sep 7 - Sep 8
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

5. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (56 reviews)
"fishing cabin."
United States
joe
The price is CA $90
CA $168 total
includes taxes & fees
Sep 7 - Sep 8
Blakley Hobbit Small Cabin

6. 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.
The price is CA $156
CA $193 total
includes taxes & fees
Sep 7 - Sep 8
The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,

7. 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.
The price is CA $125
CA $234 total
includes taxes & fees
Sep 7 - Sep 8
Blakley Hobbit Large Cabin

8. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (59 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.
The price is CA $221
CA $347 total
includes taxes & fees
Sep 8 - Sep 9
The Honey Haven

9. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
The price is CA $28
CA $58 total
includes taxes & fees
Sep 7 - Sep 8
#9 Blakley Hobbit Campground-Tent spot

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, (155 reviews)
"It was all amazing! Great hosts! Beautiful home! "
United States
Aliyah C.
The price is CA $210
CA $251 total
includes taxes & fees
Sep 7 - Sep 8
Peaceful Country Comfort W Panoramic Views of Big Creek Valley

11. 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)
"I had a great trip to Viroqua and staying definitely had a hand in that. The location makes for a perfect jumping off point for day trips in the area, has plenty of restaurants in walking distance, and shops within a short drive. Wish I would have stayed longer."
United States
Robert H.
The price is CA $131
CA $247 total
includes taxes & fees
Sep 7 - Sep 8
Cozy first floor at the heart of downtown Viroqua

12. The Incline

The Incline
Norwalk
10.0 out of 10, Exceptional, (7 reviews)
"This place is a perfect couples getaway! "
United States
Kurt T.
The price is CA $415
CA $501 total
includes taxes & fees
Sep 7 - Sep 8
The Incline

13. Country Living at its Finest

Country Living at its Finest
Viroqua
9.8 out of 10, Exceptional, (239 reviews)
"Great cabin -private but close enough to town and near many trout streams."
United States
jennifer g.
The price is CA $206
CA $305 total
includes taxes & fees
Sep 11 - Sep 12
Country Living at its Finest

14. #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.
The price is CA $28
CA $58 total
includes taxes & fees
Sep 7 - Sep 8
#10 Blakley Hobbit Campground-Tent spot

15. #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.
The price is CA $28
CA $58 total
includes taxes & fees
Sep 7 - Sep 8
#4 Blakley Hobbit Campground-Tent spot

16. Bright 4BR Retreat | UW-La Crosse

Bright 4BR Retreat | UW-La Crosse
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (43 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.
The price is CA $208
CA $632 total
includes taxes & fees
Sep 9 - Sep 10
Bright 4BR Retreat | UW-La Crosse

17. #7 Blakley Hobbit Campground-Tent spot

#7 Blakley Hobbit Campground-Tent spot
Viola
The price is CA $28
CA $58 total
includes taxes & fees
Sep 7 - Sep 8
#7 Blakley Hobbit Campground-Tent spot

18. #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.
The price is CA $28
CA $58 total
includes taxes & fees
Sep 7 - Sep 8
#8 Blakley Hobbit Campground-Tent spot

19. #6 Blakley Hobbit Campground-Tent spot

#6 Blakley Hobbit Campground-Tent spot
Viola
The price is CA $28
CA $58 total
includes taxes & fees
Sep 7 - Sep 8
#6 Blakley Hobbit Campground-Tent spot

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.
The price is CA $151
CA $229 total
includes taxes & fees
Sep 21 - Sep 22
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

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?

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.