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Portland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (60 reviews)
"This was our second year staying at this property and we loved it as much as we did last time. It’s clean, well cared for and well stocked. The owner is very easy to reach and the check in and checkout process doesn’t get much easier. The location is absolutely spectacular."
United States
Ally D.
The price is ￥46,238
￥79,636 total
includes taxes & fees
Oct 18 - Oct 19
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
9.6 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 ￥32,015
￥57,629 total
includes taxes & fees
Oct 19 - Oct 20
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)
"A great place to get away and relax."
United States
Betsy D.
The price is ￥29,407
￥35,529 total
includes taxes & fees
Oct 27 - Oct 28
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 ￥47,424
￥57,204 total
includes taxes & fees
Nov 2 - Nov 3
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, (63 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 ￥25,293
￥40,026 total
includes taxes & fees
Oct 20 - Oct 21
The Honey Haven
A grey door with a window above it and a doorbell on the right side.

6. 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)
"Nice place to stay right in town perfect for a couple "
United States
Pete G.
The price is ￥15,650
￥29,084 total
includes taxes & fees
Oct 20 - Oct 21
Cozy first floor at the heart of downtown Viroqua
A wooden cabin with a porch, deck, and outdoor seating area.

7. 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, (8 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
The price is ￥19,760
￥28,685 total
includes taxes & fees
Oct 20 - Oct 21
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
A compact kitchen with wooden walls, a sink, a microwave, a kettle, and a refrigerator.

8. 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
10.0 out of 10, Exceptional, (1 review)
"We love this place- it's simple,comfortable,clean and everything you need is availableKathe is an excellent host. Our arrival time kept changing and she was very kind and available. We are definitely returning and this will be our go to as we come to this area every few months."
United States
Debbie S.
The price is ￥17,784
￥22,098 total
includes taxes & fees
Oct 26 - Oct 27
The James a Pleasant 1-bedroom cabin in the Driftless Area near charming Viroqua
A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

9. Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.6 out of 10, Good, (58 reviews)
"fishing cabin."
United States
joe
The price is ￥10,275
￥19,180 total
includes taxes & fees
Oct 17 - Oct 18
Blakley Hobbit Small Cabin
A covered deck with outdoor furniture, a small table, and a grill.

10. 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, (35 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is ￥53,928
￥112,605 total
includes taxes & fees
Oct 20 - Oct 21
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

11. Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.2 out of 10, Very good, (48 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 ￥14,227
￥26,684 total
includes taxes & fees
Oct 18 - Oct 19
Blakley Hobbit Large Cabin
A spacious living area with a fireplace, a sofa, a dining table, and a staircase leading to an upper level.

12. 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 ￥47,430
￥57,212 total
includes taxes & fees
Oct 18 - Oct 19
The Hilltop
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

13. 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 ￥28,454
￥49,532 total
includes taxes & fees
Oct 18 - Oct 19
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
A wooden cabin interior with a pool table, sofa, kitchen, and a balcony.

14. The Hideaway

The Hideaway
Norwalk
9.6 out of 10, Exceptional, (4 reviews)
"This is a very good spot."
United States
Joe G.
The price is ￥51,383
￥62,050 total
includes taxes & fees
Oct 18 - Oct 19
The Hideaway
Two dogs sitting on a grassy field with a pond and trees in the background.

15. #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 ￥3,162
￥6,672 total
includes taxes & fees
Oct 17 - Oct 18
#10 Blakley Hobbit Campground-Tent spot
A spacious living area with a wooden floor, a curved staircase, a sofa set, and large windows offering a view.

16. Garden Ridge Retreat- Farm Stay

Garden Ridge Retreat- Farm Stay
Viroqua
10.0 out of 10, Exceptional, (19 reviews)
"Very spacious retreat with lots of space options. The farm tour was fun and educational. Really enjoyed our time here, beautiful views!"
United States
Jeri C.
The price is ￥51,566
￥95,029 total
includes taxes & fees
Nov 16 - Nov 17
Garden Ridge Retreat- Farm Stay
A modern bar area with a large flat-screen TV displaying a beach scene, wooden cabinets, neon signs, and comfortable seating.

17. Vintage Gem Near College & Downtown

Vintage Gem Near College & Downtown
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 ￥25,854
￥81,692 total
includes taxes & fees
Oct 25 - Oct 26
Vintage Gem Near College & Downtown
A modern living room with a large window, a sofa, a coffee table, and a chair.

18. “The Ridgeline” – Luxury private home, on 4 acres

“The Ridgeline” – Luxury private home, on 4 acres
Viroqua
“The Ridgeline” – Luxury private home, on 4 acres
Two dogs sitting on a grassy field with a pond and trees in the background.

19. #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 ￥3,162
￥6,672 total
includes taxes & fees
Oct 17 - Oct 18
#4 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

20. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
The price is ￥3,162
￥6,672 total
includes taxes & fees
Oct 17 - Oct 18
#9 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

Baymont by Wyndham La Crosse/Onalaska

Baymont by Wyndham La Crosse/Onalaska

8/10 Good
"good"
Michael 1-night trip
Posted 2 days ago
Baymont by Wyndham 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.