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Portland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Portland vacation rentals

A cozy living room with a wooden ceiling, a grey sofa, and a view through a glass door to an outdoor patio.

1. 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 ￥46,443
￥79,988 total
includes taxes & fees
Sep 7 - Sep 8
Secluded Rustic Cabin
A dining area with a wooden table, white chairs, and a chandelier.

2. 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 ￥33,760
￥59,571 total
includes taxes & fees
Sep 7 - Sep 8
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

3. 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 ￥33,003
￥39,889 total
includes taxes & fees
Sep 7 - Sep 8
Your adventure begins the second you arrive!
A modern interior with a wooden ceiling, a grey sofa, a staircase, and a kitchen area.

4. 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 ￥47,634
￥57,458 total
includes taxes & fees
Sep 17 - Sep 18
The Incline
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

5. 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 ￥25,405
￥40,203 total
includes taxes & fees
Sep 15 - Sep 16
The Honey Haven
Two dogs sitting on a grassy field with a pond and trees in the background.

6. #6 Blakley Hobbit Campground-Tent spot

#6 Blakley Hobbit Campground-Tent spot
Viola
The price is ￥3,176
￥6,701 total
includes taxes & fees
Oct 2 - Oct 3
#6 Blakley Hobbit Campground-Tent spot
A two-story house with a balcony on the second floor.

7. 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 ￥24,368
￥29,427 total
includes taxes & fees
Sep 6 - Sep 7
Peaceful Country Comfort W Panoramic Views of Big Creek Valley
A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

8. 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 ￥10,321
￥19,265 total
includes taxes & fees
Sep 8 - Sep 9
Blakley Hobbit Small Cabin
A spacious living area with a fireplace, a sofa, a dining table, and a staircase leading to an upper level.

9. The Hilltop

The Hilltop
Norwalk
9.6 out of 10, Exceptional, (13 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.
The price is ￥47,634
￥57,458 total
includes taxes & fees
Sep 17 - Sep 18
The Hilltop
A grey door with a window above it, a keypad lock, and a doorbell.

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.
The price is ￥15,084
￥28,326 total
includes taxes & fees
Sep 7 - Sep 8
Cozy first floor at the heart of downtown Viroqua
A wooden cabin interior with a pool table, sofa, kitchen, and a balcony.

11. 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.
The price is ￥51,604
￥62,317 total
includes taxes & fees
Oct 4 - Oct 5
The Hideaway
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

12. 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 ￥14,290
￥26,802 total
includes taxes & fees
Sep 8 - Sep 9
Blakley Hobbit Large Cabin
A covered deck with outdoor furniture, a small table, and a grill.

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

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Norwalk
9.6 out of 10, Exceptional, (32 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is ￥54,160
￥113,090 total
includes taxes & fees
Sep 7 - Sep 8
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Two dogs sitting on a grassy field with a pond and trees in the background.

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 ￥3,176
￥6,701 total
includes taxes & fees
Sep 7 - Sep 8
#10 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

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 ￥3,176
￥6,701 total
includes taxes & fees
Sep 9 - Sep 10
#4 Blakley Hobbit Campground-Tent spot
A wooden cabin with a porch, deck, and outdoor seating area.

16. 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 ￥19,848
￥28,646 total
includes taxes & fees
Sep 8 - Sep 9
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
A wooden cabin with a porch and string lights, surrounded by trees.

17. 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 ￥23,871
￥35,664 total
includes taxes & fees
Sep 11 - Sep 12
Country Living at its Finest
A wooden door with a sign reading 'The Rylan' and a welcome mat on a wooden deck with a chair.

18. 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 ￥17,863
￥22,196 total
includes taxes & fees
Sep 7 - Sep 8
The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,
Two dogs sitting on a grassy field with a pond and trees in the background.

19. #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 ￥3,176
￥6,701 total
includes taxes & fees
Sep 15 - Sep 16
#8 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

20. #5 Blakley Hobbit Campground-Tent spot

#5 Blakley Hobbit Campground-Tent spot
Viola
The price is ￥3,176
￥6,701 total
includes taxes & fees
Sep 15 - Sep 16
#5 Blakley Hobbit Campground-Tent spot
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
"Clean and friendly"
Robert 1-night trip
Posted 10 hours ago
Stoney Creek Hotel La Crosse - Onalaska

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Portland!

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.