Portland Holiday Rentals

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Holiday Rentals in Portland

Place of Peace - the Artist's Refuge
10.0 out of 10, Exceptional, (10)
"We had a lovely, peaceful stay here. The house is clean, uncluttered, and open-feeling, and the view outside is beautiful. There were small luxurious touches throughout that made this place feel loved. The location was perfect for river trips on the Kickapoo. "
United States
Catherine W.
The price is AU$382
includes taxes & fees
27 Oct - 28 Oct
Place of Peace - the Artist's Refuge
Charming 2-bedroom house with AC, WiFi in serene Norwalk
9.4 out of 10, Exceptional, (9)
"Nice clean property"
United States
Jason
The price is AU$421
includes taxes & fees
9 Nov - 10 Nov
Charming 2-bedroom house with AC, WiFi in serene Norwalk
Blakley Hobbit Large Cabin
8.4 out of 10, Very good, (37)
"Cabin with a great view of the river, BUT “bathroom” is outside with a porta potty and outdoor shower. It does have electricity and running water. Overall, I would book it again, but I’ll be better prepared for what I’m actually booking. "
United States
Mickelene H.
The price is AU$262
includes taxes & fees
26 Oct - 27 Oct
Blakley Hobbit Large Cabin
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
9.6 out of 10, Exceptional, (22)
"Twelve guys on our annual motorcycle trip. Excellent facilities, beautiful setting, and great riding in the area. Awesome porch with a gas grill and plenty of chairs. We were all impressed with this property and would absolutely book it again in the future."
United States
Jerry K.
The price is AU$1,230
includes taxes & fees
28 Oct - 29 Oct
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Blakley Hobbit Campground-Tent spot #4
10.0 out of 10, Exceptional, (2)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
The price is AU$68
includes taxes & fees
3 Nov - 4 Nov
Blakley Hobbit Campground-Tent spot #4
Quaint cabin overlooking the creek below and wetlands in the valley basin.
10.0 out of 10, Exceptional, (16)
"Great to have a quiet getaway."
United States
Fred W.
The price is AU$456
includes taxes & fees
29 Oct - 30 Oct
Quaint cabin overlooking the creek below and wetlands in the valley basin.
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
9.6 out of 10, Exceptional, (7)
"Quiet Place"
United States
Zofia Z.
The price is AU$487
includes taxes & fees
1 Nov - 2 Nov
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
The best place for star gazing all night.
10.0 out of 10, Exceptional, (8)
"Just a quick get away for the weekend. Close access to local restaurants, breweries, beautiful landscape."
United States
Heidi C.
The price is AU$539
includes taxes & fees
6 Nov - 7 Nov
The best place for star gazing all night.
The Honey Haven
10.0 out of 10, Exceptional, (45)
"This VRBO was a wonderfully clean and comfortable retreat in the driftless. The owners (and their dog) were very friendly, and the location was beautiful."
United States
Lisa K.
The price is AU$393
includes taxes & fees
6 Nov - 7 Nov
The Honey Haven
Blakley Hobbit Campground-RV spot #4
10.0 out of 10, Exceptional, (1)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
The price is AU$116
includes taxes & fees
3 Nov - 4 Nov
Blakley Hobbit Campground-RV spot #4
Blakley Hobbit Campground-Tent spot #3
The price is AU$68
includes taxes & fees
3 Nov - 4 Nov
Blakley Hobbit Campground-Tent spot #3
Blakley Hobbit Campground-Tent spot #10
10.0 out of 10, Exceptional, (2)
"The tent sites are right along the river. Not all of them have a fire pit, picnic table or grill but this is a lovely quiet serene spot to camp. "
United States
Deborah S.
The price is AU$68
includes taxes & fees
3 Nov - 4 Nov
Blakley Hobbit Campground-Tent spot #10
Blakley Hobbit Campground-RV spot #1
9.0 out of 10, Wonderful, (2)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is AU$116
includes taxes & fees
6 Nov - 7 Nov
Blakley Hobbit Campground-RV spot #1
Blakley Hobbit Campground-Tent spot #8
9.0 out of 10, Wonderful, (2)
"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 AU$68
includes taxes & fees
3 Nov - 4 Nov
Blakley Hobbit Campground-Tent spot #8
Blakley Hobbit Campground-Tent spot #7
The price is AU$68
includes taxes & fees
26 Oct - 27 Oct
Blakley Hobbit Campground-Tent spot #7
Blakley Hobbit Campground-Tent spot #9
The price is AU$68
includes taxes & fees
6 Nov - 7 Nov
Blakley Hobbit Campground-Tent spot #9
Blakley Hobbit Campground-Tent spot #5
The price is AU$68
includes taxes & fees
26 Oct - 27 Oct
Blakley Hobbit Campground-Tent spot #5
Blakley Hobbit Campground-RV spot #2
The price is AU$116
includes taxes & fees
6 Nov - 7 Nov
Blakley Hobbit Campground-RV spot #2
Blakley Hobbit Campground-Tent spot #2
The price is AU$68
includes taxes & fees
26 Oct - 27 Oct
Blakley Hobbit Campground-Tent spot #2
Blakley Hobbit Campground-RV spot #3
6.0 out of 10, (1)
"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 AU$116
includes taxes & fees
6 Nov - 7 Nov
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

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, 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 favourite 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 depend 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 AU$189 per night. Entering your travel dates in the search wizard might find you 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?

Place of Peace - the Artist's Refuge : This holiday home rental outside of Portland is located on a river, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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. Branches Winery and Elroy Sparta State 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.