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Portland Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (59 reviews)
"What a wonderful property! "
United States
Becky K.
The price is SAR 1,098
SAR 1,773 total
includes taxes & fees
30 Sep - 1 Oct
Secluded Rustic Cabin
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

2. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"A great place to get away and relax."
United States
Betsy D.
The price is SAR 665
SAR 780 total
includes taxes & fees
6 Oct - 7 Oct
Your adventure begins the second you arrive!
A dining area with a wooden table, white chairs, and a chandelier.

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

Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Cashton
9.6 out of 10, Exceptional, (4 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 SAR 747
SAR 1,279 total
includes taxes & fees
30 Sep - 1 Oct
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
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 SAR 1,126
SAR 1,287 total
includes taxes & fees
30 Sep - 1 Oct
The Incline
A wooden cabin with a porch, deck, and outdoor seating area.

5. 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 SAR 469
SAR 673 total
includes taxes & fees
4 Oct - 5 Oct
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
A wooden interior with a table, bench, window, blinds, and a mounted television.

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, (3 reviews)
"Beautiful location"
United States
Brittany
The price is SAR 439
SAR 543 total
includes taxes & fees
26 Oct - 27 Oct
The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,
A rural landscape with a wooden fence, a field of crops, and distant buildings including a silo and a house.

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, (159 reviews)
"Loved the view and the peaceful setting! Very comfortable apartment, everything we needed and more. Perfect stay!"
United States
Nancy
The price is SAR 571
SAR 682 total
includes taxes & fees
30 Sep - 1 Oct
Peaceful Country Comfort W Panoramic Views of Big Creek Valley
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

8. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (62 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 SAR 601
SAR 911 total
includes taxes & fees
19 Oct - 20 Oct
The Honey Haven
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

9. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (47 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 SAR 338
SAR 634 total
includes taxes & fees
5 Oct - 6 Oct
Blakley Hobbit Large Cabin
A grey door with a window above it and a doorbell on the right side.

10. Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
10.0 out of 10, Exceptional, (62 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 SAR 383
SAR 703 total
includes taxes & fees
13 Oct - 14 Oct
Cozy first floor at the heart of downtown Viroqua
A spacious living area with a fireplace, a sofa, a dining table, and a staircase leading to an upper level.

11. 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 SAR 1,126
SAR 1,287 total
includes taxes & fees
30 Sep - 1 Oct
The Hilltop
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

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

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (18 reviews)
"Our stay was perfect! The host was easy to communicate with and even let us check in early. The place was so cute! The bed was super comfortable and everything looked good and felt clean. Very safe area and neighborhood. Such a bonus to have a restaurant attached to the property! We will for sure stay here again!"
United States
Heather
The price is SAR 409
SAR 622 total
includes taxes & fees
1 Oct - 2 Oct
Hidden Gem - 1BR/1Bath in Lax WI
Two dogs sitting on a grassy field with a pond and trees in the background.

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
The price is SAR 188
SAR 277 total
includes taxes & fees
30 Sep - 1 Oct
Blakley Hobbit Campground-RV spot #4
A compact kitchen with wooden walls, a sink, a microwave, a kettle, and a refrigerator.

14. The James a Pleasant 1-bedroom cabin in the Driftless Area near charming Viroqua

The James a Pleasant 1-bedroom cabin in the Driftless Area near charming Viroqua
Viroqua
The price is SAR 422
SAR 525 total
includes taxes & fees
30 Sep - 1 Oct
The James a Pleasant 1-bedroom cabin in the Driftless Area near charming Viroqua
A wooden cabin interior with a pool table, sofa, kitchen, and a balcony.

15. The Hideaway

The Hideaway
Norwalk
9.4 out of 10, Exceptional, (3 reviews)
"Extremely smooth experience. Pictures were very representative of actual cabin conditions. Would happily return for a longer stay."
United States
John H.
The price is SAR 1,220
SAR 1,394 total
includes taxes & fees
30 Sep - 1 Oct
The Hideaway
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

16. 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, (18 reviews)
"excellent out of the way retreat close to things we wanted to do and great place for us and our cats, the hot tub was a great treat"
United States
Joseph W.
The price is SAR 676
SAR 1,176 total
includes taxes & fees
30 Sep - 1 Oct
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

17. Bluff View Haven | Steps to Campus

Bluff View Haven | Steps to Campus
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 SAR 564
SAR 1,615 total
includes taxes & fees
30 Sep - 1 Oct
Bluff View Haven | Steps to Campus
A covered deck with outdoor furniture, a small table, and a grill.

18. 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, (34 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is SAR 1,281
SAR 2,512 total
includes taxes & fees
6 Oct - 7 Oct
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
A two-story house with a balcony, surrounded by a forest.

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

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
10.0 out of 10, Exceptional, (12 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is SAR 667
SAR 1,282 total
includes taxes & fees
5 Oct - 6 Oct
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
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

Country Inn & Suites by Radisson, Sparta, WI

Country Inn & Suites by Radisson, Sparta, WI

8/10 Good
"Hot tub title needs a cleaning and some title work. They could use more staff to keep up with breakfast"
kimberly 2-night trip
Posted 14 hours ago
Country Inn & Suites by Radisson, Sparta, WI

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.