Portland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Portland vacation rentals

Exterior

Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very Good, (40 reviews)
"We enjoyed our stay, spending most of our time kayaking and hiking!! Beautiful quiet area and clean accommodations."
United States
Denise R.
The price is ￥14,278
￥26,779 total
includes taxes & fees
Apr 19 - Apr 20
Blakley Hobbit Large Cabin
Terrace/patio

Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.8 out of 10, Good, (51 reviews)
"Enjoy our stay."
United States
Sondra M.
The price is ￥10,312
￥19,248 total
includes taxes & fees
Apr 20 - Apr 21
Blakley Hobbit Small Cabin
Exterior

Place of Peace - the Artist's Refuge

Place of Peace - the Artist's Refuge
La Farge
9.6 out of 10, Exceptional, (18 reviews)
"Easy in and out, the house had everything we needed, and the view was amazing!"
United States
shoua x.
The price is ￥20,703
￥39,416 total
includes taxes & fees
Apr 19 - Apr 20
Place of Peace - the Artist's Refuge
1 bedroom, desk, free WiFi, bed sheets

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (27 reviews)
"Beautiful relaxing getaway!"
United States
Amanda M.
The price is ￥38,550
￥46,530 total
includes taxes & fees
Apr 20 - Apr 21
Your adventure begins the second you arrive!
Interior

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (47 reviews)
"Excellent stay. Clean with beautiful surroundings and a great dog to greet you."
United States
Jason B.
The price is ￥25,382
￥40,167 total
includes taxes & fees
Apr 23 - Apr 24
The Honey Haven
Smart TV, fireplace

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

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is ￥28,555
￥49,708 total
includes taxes & fees
Apr 19 - Apr 20
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Property grounds

Blakley Hobbit Campground-Tent spot #4

Blakley Hobbit Campground-Tent spot #4
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 ￥3,173
￥6,695 total
includes taxes & fees
Apr 19 - Apr 20
Blakley Hobbit Campground-Tent spot #4
Exterior detail

Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
10.0 out of 10, Exceptional, (55 reviews)
"Wonderful place! Clean, full of amenities, within walking distance to everything downtown has to offer."
United States
Alina L.
The price is ￥15,229
￥28,479 total
includes taxes & fees
Apr 27 - Apr 28
Cozy first floor at the heart of downtown Viroqua
Exterior

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
The price is ￥19,830
￥28,620 total
includes taxes & fees
Apr 19 - Apr 20
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Interior

Vintage Spring Getaway

Vintage Spring Getaway
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (34 reviews)
"Our stay was very nice. Tina was excellent in responding to a few of our needs. Lovey home and nicely decorated."
United States
Mary B.
The price is ￥19,189
￥66,400 total
includes taxes & fees
Apr 20 - Apr 21
Vintage Spring Getaway
1 bedroom, WiFi, bed sheets

Hidden Gem - 1BR/1Bath in Lax WI

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (16 reviews)
"A lovely, spacious, clean apartment above a yummy restaurant in a quiet residential neighborhood. We stayed there when we were in town for a 6-hour race in Goose Island State Park, and it was perfect! "
United States
Amy
The price is ￥17,292
￥26,271 total
includes taxes & fees
Apr 20 - Apr 21
Hidden Gem - 1BR/1Bath in Lax WI
Private kitchen

Jake's Place

Jake's Place
Powell-Poage-Hamilton
9.8 out of 10, Exceptional, (8 reviews)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is ￥23,796
￥52,177 total
includes taxes & fees
Apr 21 - Apr 22
Jake's Place
Exterior

Wagonwheel Ranch

Wagonwheel Ranch
Viroqua
9.8 out of 10, Exceptional, (19 reviews)
"Beautiful place"
United States
Francis H.
The price is ￥44,261
￥82,011 total
includes taxes & fees
Apr 27 - Apr 28
Wagonwheel Ranch
Dining

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 ￥39,263
￥66,528 total
includes taxes & fees
Apr 22 - Apr 23
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
2 bedrooms, WiFi, bed sheets

Farm Stay, convenient yet quiet - complete with cows in the backyard!

Farm Stay, convenient yet quiet - complete with cows in the backyard!
Bangor
The price is ￥16,023
￥24,436 total
includes taxes & fees
Apr 21 - Apr 22
Farm Stay, convenient yet quiet - complete with cows in the backyard!
Private kitchen

Historic 1922 Colonel May Schoolhouse

Historic 1922 Colonel May Schoolhouse
Viroqua
10.0 out of 10, Exceptional, (1 review)
The price is ￥39,977
￥48,201 total
includes taxes & fees
Apr 20 - Apr 21
Historic 1922 Colonel May Schoolhouse
Exterior

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, (58 reviews)
"The house is very historic and has great amenities!"
United States
Kaylee R.
The price is ￥29,269
￥37,674 total
includes taxes & fees
Apr 20 - Apr 21
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Property grounds

Blakley Hobbit Campground-RV spot #1

Blakley Hobbit Campground-RV spot #1
Viola
9.0 out of 10, Wonderful, (2 reviews)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is ￥7,932
￥11,716 total
includes taxes & fees
Apr 19 - Apr 20
Blakley Hobbit Campground-RV spot #1
Property grounds

Blakley Hobbit Campground-Tent spot #10

Blakley Hobbit Campground-Tent spot #10
Viola
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Huan B.
The price is ￥3,173
￥6,695 total
includes taxes & fees
Apr 19 - Apr 20
Blakley Hobbit Campground-Tent spot #10
Living area

“The Ridgeline” – Luxury private home, on 4 acres

“The Ridgeline” – Luxury private home, on 4 acres
Viroqua
The price is ￥28,412
￥46,713 total
includes taxes & fees
Apr 26 - Apr 27
“The Ridgeline” – Luxury private home, on 4 acres
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portland Hotel Reviews

Holiday Inn Express & Suites Onalaska La Crosse Area by IHG

Holiday Inn Express & Suites Onalaska La Crosse Area by IHG

10/10 Excellent
"Staff was very friendly any time of day or night. Room was very clean , bed was extremely comfortable, and the bathroom had Kohler fixtures. If i'm in the area again , I would definitely stay at the holiday inn midwest."
Cathy 2-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Onalaska La Crosse Area by IHG

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

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?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This vacation home rental near 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 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 Vernon Vineyards 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.