Portland Holiday Rentals

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Our top choices for Portland holiday rentals

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

Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.
Stoddard
10.0 out of 10, Exceptional, (410)
"The house was amazing and view outside was beautiful. We enjoyed our stay. We definitely would rent again."
United States
Shawn K.
Secluded, Romantic, Family Friendly and Cozy, Last House in the Valley.

Spacious Dog-Friendly 5BR Near UWL w/ Fire Pit & Fenced Yard

Spacious Dog-Friendly 5BR Near UWL w/ Fire Pit & Fenced Yard
Grandview-Emerson
10.0 out of 10, Exceptional, (51)
"Quiet and great location."
United States
Jeremy S.
Spacious Dog-Friendly 5BR Near UWL w/ Fire Pit & Fenced Yard

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

Lakeside cabin with Hot Tub and full kitchen! Sleeps up to 12 people.
Tomah
9.2 out of 10, Wonderful, (47)
"Well designed property with all the amenities. Everyone had plenty of space, and there is a nice porch and back deck for relaxing. The hot tub was well maintained and appreciated. The location was remote enough to be a getaway while being only minutes away from Tomah. "
United States
John G.
Lakeside cabin with Hot Tub and full kitchen! Sleeps up to 12 people.

Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.8 out of 10, Good, (51)
"Enjoy our stay."
United States
Sondra M.
Blakley Hobbit Small Cabin

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Historic Downtown La Crosse
9.8 out of 10, Exceptional, (50)
"Amazing house, great location, excellent host!"
United States
Ed R.
The price is AU$408
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Powell-Poage-Hamilton
10.0 out of 10, Exceptional, (157)
"Really enjoyed our stay here. Stayed just a couple nights and everything was clean, comfortable and cozy. Location was perfect for our needs. Would highly recommend.."
United States
Mary B.
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Place of Peace - the Artist's Refuge

Place of Peace - the Artist's Refuge
La Farge
9.8 out of 10, Exceptional, (17)
"It was great! The place is calm and quiet and surrounded by beautiful nature. Best place to decompress before classes start."
United States
Claudia S.
The price is AU$373
includes taxes & fees
15 Dec - 16 Dec
Place of Peace - the Artist's Refuge

Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

Arcadian Cabin at Bishop Branch, creek-front, public land access, great location
Viroqua
10.0 out of 10, Exceptional, (266)
"We loved the cabin! It was so relaxing to sit on the porch and enjoy the view. Jake and Becky made the stay very welcoming and responded to any questions that we had about the house. The location was perfect, being less than 10 minutes from shops and restaurants in Viroqua. Would definitely stay again!"
United States
Denise Z.
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.
Westby
10.0 out of 10, Exceptional, (15)
"Was such a charming property. We were made to feel very welcome. I’d like to go back and stay again."
United States
Julie
Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

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

Quaint cabin overlooking the creek below and wetlands in the valley basin.
Norwalk
10.0 out of 10, Exceptional, (19)
"Perfect little place for a getaway. Clean, comfortable and nice amenities for a cabin in the woods. Beautiful setting, and still within driving distance of restaurants and other recreational activities."
United States
Nathan U.
The price is AU$445
includes taxes & fees
18 Dec - 19 Dec
Quaint cabin overlooking the creek below and wetlands in the valley basin.

Lakeside Ranch Cabin.

Lakeside Ranch Cabin.
Tomah
8.8 out of 10, Excellent, (78)
"Great location and atmosphere. The kitchen was adequate for our needs, and we loved the hot tub every evening. The lawn was cut fresh, the lake was nice, the decking added nostalgia. We really enjoyed ourselves. "
United States
pamalarenee1
Lakeside Ranch Cabin.

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, (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$1,340
includes taxes & fees
16 Dec - 17 Dec
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

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

Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples
La Crosse
10.0 out of 10, Exceptional, (109)
"The numerous amenities, open layout, comfortable living spaces and cleanliness made this trip so enjoyable for the whole family. Our hosts really went above and beyond to make the stay stress-free. The kitchen was very functional and made for great, family dinners without the need to go out. We recommend this location and would return again! "
United States
Rebecca N.
Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples

Queen Anne Stay

Queen Anne Stay
Viroqua
10.0 out of 10, Exceptional, (13)
"The house has lots of space and is just blocks from great dining and bars. Will absolutely book this again for future trips to Viroqua. "
United States
Oren S.
Queen Anne Stay

Sunlit & spacious home in a quiet, natural setting

Sunlit & spacious home in a quiet, natural setting
La Crosse
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. "
United States
Solomon C.
Sunlit & spacious home in a quiet, natural setting

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities
La Crosse
10.0 out of 10, Exceptional, (42)
"House was well appointed with everything you need, the pool was great and the hosts even better!"
United States
Adam S.
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Tomah
8.8 out of 10, Excellent, (93)
"Great place. Will definitely come again. "
United States
Heather S.
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

NEW! Manor on Main- Celebrations, Reunions, Events

NEW! Manor on Main- Celebrations, Reunions, Events
Grandview-Emerson
9.4 out of 10, Exceptional, (15)
"We thoroughly enjoyed our stay in La Crosse and at the Manor on Main. The accommodations were very nice and worked well for our family reunion. We were a short walk from downtown and the river and the neighborhood was great."
United States
Janet W.
NEW! Manor on Main- Celebrations, Reunions, Events

Jake's Place

Jake's Place
Powell-Poage-Hamilton
9.8 out of 10, Exceptional, (8)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is AU$448
includes taxes & fees
4 Jan - 5 Jan 2026
Jake's Place

Capeside Cottage

Capeside Cottage
Bluffside
9.8 out of 10, Exceptional, (19)
"Great location with easy access to downtown. Game room was fun for our family. Beds were very comfortable. "
United States
Scott B.
Capeside Cottage
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$373 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?

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities: This holiday home rental outside of Portland is located on a river, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.