Portland Holiday Rentals

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Holiday Rentals in Portland

Blakley Hobbit Small Cabin

7.8 out of 10, Good, (48)
"Small, not fit for two people, photo was misleading, hard to find. Don’t advertise as a hobbit house. Couldn’t get hold of the owners. Sorry you guys, not any where near what advertised. Sorry. "
The price is NZ$210
includes taxes & fees
1 Oct - 2 Oct
Blakley Hobbit Small Cabin

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. "
The price is NZ$292
includes taxes & fees
5 Oct - 6 Oct
Blakley Hobbit Large Cabin

Secluded Rustic Cabin

10.0 out of 10, Exceptional, (51)
"This property is gorgeous! House is spacious and decks are great. "
The price is NZ$850
includes taxes & fees
1 Oct - 2 Oct
Secluded Rustic Cabin

Your Home Away From Home

9.6 out of 10, Exceptional, (146)
"This place is awesome and the owners are fantastic. If you are looking for a quiet place to relax, do some amazing trout fishing, and enjoy great people. This is your place !"
Your Home Away From Home

Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.

10.0 out of 10, Exceptional, (404)
"Had a wonderful stay at the property! "
Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.

Place of Peace - the Artist's Refuge

10.0 out of 10, Exceptional, (9)
"What a beautiful location! We went hiking and enjoyed the scenery. Loved the baby cows across the road. Thank you for sharing with us!"
The price is NZ$427
includes taxes & fees
1 Oct - 2 Oct
Place of Peace - the Artist's Refuge

Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

10.0 out of 10, Exceptional, (236)
"Great place to stay, the area was beautiful and the place was immaculate!"
Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

Lakeside cabin with Hot Tub and full kitchen! Sleeps up to 12 people.

9.0 out of 10, Wonderful, (41)
"We had a great time "
Lakeside cabin with Hot Tub and full kitchen! Sleeps up to 12 people.

Cabin in Beautiful Timber Coulee

10.0 out of 10, Exceptional, (89)
"Great place with excellent access to local fishing. We had a great stay!"
Cabin in Beautiful Timber Coulee

Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples

10.0 out of 10, Exceptional, (108)
"Nice open space for cooking/family time and kids loved playing school/writing on chalk board!"
Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples

Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View

9.8 out of 10, Exceptional, (144)
"Great spot for trout fishing and a great place to stay and relax on the porch after a full day exploring the many trout streams."
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View

3BR Ranch / Near Hospitals, Universities, Bluff, River, Coffee Shop, & More!

10.0 out of 10, Exceptional, (6)
"Lots of room. Large beds & bedrooms. Entire interior has been updated and is very cozy. The local Coffee house next door was an awesome bonus. "
3BR Ranch / Near Hospitals, Universities, Bluff, River, Coffee Shop, & More!

Quaint cabin overlooking the creek below and wetlands in the valley basin.

10.0 out of 10, Exceptional, (14)
"Great to have a quiet getaway."
The price is NZ$506
includes taxes & fees
1 Oct - 2 Oct
Quaint cabin overlooking the creek below and wetlands in the valley basin.

Jake's Place

9.8 out of 10, Exceptional, (6)
"Was so much better than the large groups of people at motels and quit"
The price is NZ$510
includes taxes & fees
12 Oct - 13 Oct
Jake's Place

Riverview Cabin home!

9.6 out of 10, Exceptional, (47)
"Great location and space for a family gathering. The house was well appointed and clean. Lots of room for our group of 10!"
Riverview Cabin home!

Cozy Newly Built Cabin with Scenic Views

10.0 out of 10, Exceptional, (77)
"Beautiful stay! Quiet, close enough to town to go out and about! Very clean and comfortable. "
Cozy Newly Built Cabin with Scenic Views

This big old charming house Viroqua

10.0 out of 10, Exceptional, (33)
"Had a really nice time and would definitely book future stays at this house."
This big old charming house Viroqua

Small Cabin on West Fork Kickapoo River

9.4 out of 10, Exceptional, (21)
"This was a very quaint, well kept little house, and it was perfect for our group and the best part was that it had a first class trout stream right in the backyard. And we actually caught a few fish. Loved this place and would like to go there again."
Small Cabin on West Fork Kickapoo River

Sunlit & spacious home in a quiet, natural setting

10.0 out of 10, Exceptional, (1)
"Very fun area for access to the outdoors and the host was very kind! Thanks and will definitely come back. "
Sunlit & spacious home in a quiet, natural setting

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

9.6 out of 10, Exceptional, (7)
"Nice place across from a campground. "
The price is NZ$542
includes taxes & fees
15 Oct - 16 Oct
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
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

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 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 NZ$210 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?

Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.: This holiday home rental outside of Portland is located in a rural location, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. It has 5 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. 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.