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Holiday Rentals in Portland

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Check prices for these dates

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

Our top choices for Portland holiday rentals

A wooden deck with a barbecue grill, overlooking a river and autumn foliage.

1. 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 €113
includes taxes & fees
15 Oct - 16 Oct
Blakley Hobbit Small Cabin
A wooden interior with a table, bench, window, blinds, and a mounted television.

2. 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, (4 reviews)
"Beautiful location"
United States
Brittany
The Rylan a Cozy 1-bedroom cabin in serene Driftless area just outside Viroqua,
A wooden cabin with a porch, deck, and outdoor seating area.

3. 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 €166
includes taxes & fees
18 Oct - 19 Oct
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

4. 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 €209
includes taxes & fees
27 Oct - 28 Oct
Your adventure begins the second you arrive!
A rustic wooden cabin with a front porch, a staircase, and a small deck area.

5. 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 €155
includes taxes & fees
18 Oct - 19 Oct
Blakley Hobbit Large Cabin
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 €167
includes taxes & fees
20 Oct - 21 Oct
Cozy first floor at the heart of downtown Viroqua
A dining area with a wooden table, white chairs, and a chandelier.

7. 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 €393
includes taxes & fees
14 Nov - 15 Nov
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Two dogs sitting on a grassy field with a pond and trees in the background.

8. 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 €70
includes taxes & fees
15 Oct - 16 Oct
Blakley Hobbit Campground-RV spot #4
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

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

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (19 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 €152
includes taxes & fees
15 Oct - 16 Oct
Hidden Gem - 1BR/1Bath in Lax WI
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

10. 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 €230
includes taxes & fees
20 Oct - 21 Oct
The Honey Haven
A cozy living room with a wooden ceiling, a grey sofa, and a view through a glass door to an outdoor patio.

11. 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.
Secluded Rustic Cabin
A modern interior with a wooden ceiling, a grey sofa, a staircase, and a kitchen area.

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 €326
includes taxes & fees
15 Oct - 16 Oct
The Incline
A compact kitchen with wooden walls, a sink, a microwave, a kettle, and a refrigerator.

13. 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 €129
includes taxes & fees
26 Oct - 27 Oct
The James a Pleasant 1-bedroom cabin in the Driftless Area near charming Viroqua
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television.

14. 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 €281
includes taxes & fees
15 Oct - 16 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.

15. 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.
Vintage Gem Near College & Downtown
Two dogs sitting on a grassy field with a pond and trees in the background.

16. #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 €42
includes taxes & fees
15 Oct - 16 Oct
#4 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

17. Blakley Hobbit Campground-RV spot #1

Blakley Hobbit Campground-RV spot #1
Viola
9.0 out of 10, Wonderful, (4 reviews)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is €70
includes taxes & fees
18 Oct - 19 Oct
Blakley Hobbit Campground-RV spot #1
Two dogs sitting on a grassy field with a pond and trees in the background.

18. #9 Blakley Hobbit Campground-Tent spot

#9 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (1 review)
The price is €42
includes taxes & fees
15 Oct - 16 Oct
#9 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

19. #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 €42
includes taxes & fees
15 Oct - 16 Oct
#10 Blakley Hobbit Campground-Tent spot
Two dogs sitting on a grassy field with a pond and trees in the background.

20. Blakley Hobbit Campground-RV spot #3

Blakley Hobbit Campground-RV spot #3
Viola
6.0 out of 10, (1 review)
"This is a beautiful property. The price is a little high for the lack of amenities and the road was busier than I expected but we loved the place anyhow. "
United States
Kirstin
The price is €70
includes taxes & fees
28 Oct - 29 Oct
Blakley Hobbit Campground-RV spot #3
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

10/10 Excellent
"Our room was clean. The staff was always busy cleaning, taking care of the pool, etc. The staff was always friendly. The property is in the middle of a major renovation, where they are removing everything in the upper floors and rebuilding them."
Mike 1-night trip
Posted 16 hours ago
Baymont by Wyndham La Crosse/Onalaska

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as €155 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Portland has to offer?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This holiday home rental outside of 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 that 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 wider area.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for families.