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Check prices for these dates

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

Our top choices for Portland holiday 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 £366
includes taxes & fees
13 Sept - 14 Sept
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 £283
includes taxes & fees
7 Sept - 8 Sept
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 £184
includes taxes & fees
7 Sept - 8 Sept
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 £273
includes taxes & fees
7 Sept - 8 Sept
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 £187
includes taxes & fees
8 Sept - 9 Sept
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 £34
includes taxes & fees
6 Sept - 7 Sept
#6 Blakley Hobbit Campground-Tent spot
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, (155 reviews)
"It was all amazing! Great hosts! Beautiful home! "
United States
Aliyah C.
The price is £137
includes taxes & fees
6 Sept - 7 Sept
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 £93
includes taxes & fees
7 Sept - 8 Sept
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 £273
includes taxes & fees
8 Sept - 9 Sept
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)
"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 £135
includes taxes & fees
7 Sept - 8 Sept
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 £295
includes taxes & fees
7 Sept - 8 Sept
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 £128
includes taxes & fees
7 Sept - 8 Sept
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 £534
includes taxes & fees
7 Sept - 8 Sept
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 £34
includes taxes & fees
6 Sept - 7 Sept
#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 £34
includes taxes & fees
6 Sept - 7 Sept
#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 £137
includes taxes & fees
6 Sept - 7 Sept
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 £168
includes taxes & fees
11 Sept - 12 Sept
Country Living at its Finest
A rural setting with two wooden cabins, one with an attached garage, and a red car parked nearby.

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 £106
includes taxes & fees
6 Sept - 7 Sept
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 £34
includes taxes & fees
6 Sept - 7 Sept
#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 £34
includes taxes & fees
6 Sept - 7 Sept
#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

AmericInn by Wyndham West Salem

AmericInn by Wyndham West Salem

8/10 Good
"The body soap and shampoo containers were empty in the shower unit. Luckily I carry my own as a back up."
John 1-night trip
Posted 8 hours ago
AmericInn by Wyndham West Salem

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 £93 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.