Portland Vacation Rentals

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Vacation Rentals in Portland

TV, DVD player, books, video library
Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.
10.0 out of 10, Exceptional, (347)
"Perfect place for a quiet getaway. Owners were super communicative and helpful, and the house was perfectly clean and comfortable. Loved it!"
Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.
Exterior
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
10.0 out of 10, Exceptional, (104)
"8th St Blues was the perfect place for our girls weekend!"
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Fridge, microwave, oven, stovetop
NEW LISTING Riverview Cabin home!
9.6 out of 10, Exceptional, (34)
"We loved our stay. It was perfect for our group gathering."
NEW LISTING Riverview Cabin home!
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Property grounds
Driftless Area Country House: large deck, spring fed creek, Amish area
10.0 out of 10, Exceptional, (57)
"What a fantastic property! There were 6 of us for a Girl’s weekend and we were very comfortable. The house was beautiful with 5 bedrooms, kitchen and bath well-stocked with everything you could need, and very clean! It is a very remote location which was great for us. It was 45 minutes to LaCrosse which did not bother us, but something visitors should not glaze over in the listing as Rose is sure to note that. This property was even better than we expected. We are already talking about a return...
Driftless Area Country House: large deck, spring fed creek, Amish area
Property grounds
Quiet countryside shipping container home. Relax or enjoy outdoor recreation
10.0 out of 10, Exceptional, (50)
"We really loved our stay from the uniqueness of the home to the spotless and so well thought out for all the amenities. Loved the property location. Highly recommend!"
Quiet countryside shipping container home. Relax or enjoy outdoor recreation
Property grounds
Your Home Away From Home
9.6 out of 10, Exceptional, (122)
"Great space, great area, and so thankful this was pet friendly. The park down the road had a walking path that was perfect for our dogs to get out and exercise. Definitely hoping we will be welcomed back!"
Your Home Away From Home
Property grounds
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
8.8 out of 10, Excellent, (64)
"We loved the cabin. It was quiet and peaceful. Just what we were looking for."
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.
Exterior
Cozy Newly Built Cabin with Scenic Views
10.0 out of 10, Exceptional, (27)
"We had a storm and power was out. chad called and then brought flashlights. Good job keeping us comfortable for the brief inconvenience. Nice place, quiet and clean."
Cozy Newly Built Cabin with Scenic Views
Smart TV, fireplace
Secluded luxury House in the Hills w/king bed
10.0 out of 10, Exceptional, (13)
"We enjoyed the home tremendously-it was as beautiful as the photos and Tiffany was extremely accommodating. We appreciated all the details she saw to for our comfort and enjoyment. We would definitely ity stay again!"
Secluded luxury House in the Hills w/king bed
Fridge, microwave, oven, stovetop
Exquisite comfort for family and friends in the heart of Downtown Viroqua.
10.0 out of 10, Exceptional, (214)
"We all loved the Lodge. It was a great condo. Very well appointed. Very clean. Very spacious. Awesome location. The Viroqua Farmers Market was just a block away. Awesome market too!!"
Exquisite comfort for family and friends in the heart of Downtown Viroqua.
Fridge, microwave, oven, stovetop
Capeside Cottage
9.8 out of 10, Exceptional, (7)
"House was clean and well stocked with towels and kitchen supplies. Communication with host was good-very quick to respond to any questions or requests. Nice weekend in a quiet neighborhood!"
Capeside Cottage
Property grounds
Marina getaway located on the back sloughs of the mighty Mississippi.
10.0 out of 10, Exceptional, (38)
"If you’re a couple looking for the absolutely perfect place to stay, this is it. Quiet, charming and a beautiful setting. A short drive to anywhere in the area. We loved every part of this place! Next time we come to La Crosse and this place isn’t available we’ll have to change dates. Thanks Emily for such a great space!"
Marina getaway located on the back sloughs of the mighty Mississippi.
Smart TV, fireplace
Cabin in Beautiful Timber Coulee
10.0 out of 10, Exceptional, (53)
"We had a great stay here for a trout fishing trip. The cabin is very nice, well appointed and quiet. The host was very communicative and helpful. I would certainly recommend staying here and will look to stay here again myself. We've stayed at a number of places in the driftless and this stay was one of the best."
Cabin in Beautiful Timber Coulee
Property grounds
Rocky Ridge Retreat - A new modern rustic cabin.
10.0 out of 10, Exceptional, (27)
"A very peaceful and quiet place for a getaway. We really enjoyed our stay and found the place to be very clean and had everything we needed. The area offers several parks for a day of hiking."
Rocky Ridge Retreat - A new modern rustic cabin.
Private kitchen | Fridge, microwave, oven, stovetop
Cozy first floor at the heart of downtown Viroqua
9.8 out of 10, Exceptional, (18)
"The place worked great for our short stay!"
The price is $95
$178 total
includes taxes & fees
May 6 - May 7
Cozy first floor at the heart of downtown Viroqua
Exterior
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location
10.0 out of 10, Exceptional, (208)
"Lovely cabin in a beautiful setting. Cozy, comfortable. Hope to come back soon."
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location
Fridge, microwave, oven, stovetop
Blakley Hobbit Large Cabin
8.2 out of 10, Very Good, (22)
"My son turned 10 and for his birthday wanted to go to a cabin and fish all wknd with a couple friends. This cabin was perfect, they could wake up and walk right out to the river and fish at their leisure."
The price is $90
$169 total
includes taxes & fees
May 2 - May 3
Blakley Hobbit Large Cabin
View from property
The Honey Haven
10.0 out of 10, Exceptional, (10)
"The house was beautiful & had everything we needed. Hosts were very responsive to any questions we had. We would definitely stay here again!"
The price is $160
$252 total
includes taxes & fees
May 6 - May 7
The Honey Haven
Property grounds
Birch Lake Secluded Getaway- Serenity home 5 bedroom sleeps up to 14
9.0 out of 10, Wonderful, (35)
"Other than the fact that we came in the blizzard of Jan. 2024, this place was perfect for us. It had more than ample space for 11 people to sleep. The hot tub was an added bonus for a few of our group. One slept next to the fireplace on our last night. The only downside we had, and thats no fault of anyone but mother nature, was it can be difficult to find on the backroads of Tomah in a snow storm. They did a great job keeping us plowed out. Overall, we were all very happy with our stay and will...
Birch Lake Secluded Getaway- Serenity home 5 bedroom sleeps up to 14
View from property
Beautiful secluded cabin with amazing country views
10.0 out of 10, Exceptional, (9)
"Loved this cozy house for a relaxing weekend with friends. Saw so many birds sitting in the lovely back deck!"
Beautiful secluded cabin with amazing country views
Don't see what you're looking for?
See all available properties in Portland
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.

Other types of properties in Portland you may be interested in

Interior
Stoney Creek Hotel La Crosse - Onalaska
2.5 star property
9.0 out of 10, Wonderful, (1315)
"Clean, modern, good free breakfast, nice hot tub and indoor/outdoor pool."
The price is $106
$120 total
includes taxes & fees
May 5 - May 6
Stoney Creek Hotel La Crosse - Onalaska
Sports facility
Hampton Inn Lacrosse/Onalaska
2.5 star property
9.0 out of 10, Wonderful, (635)
"The pool is chilly. The hot tube is cold. Breakfast sausage is cold. "
The price is $101
$115 total
includes taxes & fees
May 28 - May 29
Hampton Inn Lacrosse/Onalaska
Indoor pool
AmericInn by Wyndham West Salem
2.5 star property
8.4 out of 10, Very Good, (684)
"Liked the decor in the room. Clean and great for what we needed!"
The price is $64
$70 total
includes taxes & fees
May 26 - May 27
AmericInn by Wyndham West Salem
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.

Everything you need to know about Portland vacation rentals

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

Portland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland vacation 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 vacation.

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 vacation rental in Portland?

Yes, you can find vacation rentals near top sights in Portland, or you can choose a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Portland?

Secluded, Romantic, Family Friendly And Cozy, Last House In The Valley.: This vacation home rental near Portland is located in a rural location and has a balcony, a selection of games, and a barbecue grill 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 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. LaCrosse River Trail and La Crosse Fairgrounds Speedway are a couple of places you'll find in the larger area.

What are vacation rentals like in Portland?

Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Portland. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.

Recent reviews of Portland properties
Expedia verified reviews

Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel

Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel

5/5 Excellent
"Awesome place to stay. Mason was beyond helpful"
A verified traveler stayed at Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel
Posted 10 hours ago
Holiday Inn Express & Suites Onalaska La Crosse Area, an IHG Hotel