Portland Holiday Rentals

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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Portland holiday rentals

1 bedroom, desk, free WiFi, bed sheets

Cabin in Norwalk

Your adventure begins the second you arrive!
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful relaxing getaway!"
United States
Amanda M.
The price is HK$1,897
HK$2,248 total
includes taxes & fees
8 Mar - 9 Mar
Your adventure begins the second you arrive!
Exterior

Holiday Home in La Farge

Place of Peace - the Artist's Refuge
9.8 out of 10, Exceptional, (17 reviews)
"Easy in and out, the house had everything we needed, and the view was amazing!"
United States
shoua x.
The price is HK$1,021
HK$1,943 total
includes taxes & fees
5 Mar - 6 Mar
Place of Peace - the Artist's Refuge
Exterior

Cabin in Viola

Blakley Hobbit Large Cabin
8.0 out of 10, Very good, (40 reviews)
"House was exactly as described. Easy to find. Fun for the kids!"
United States
Emily K.
The price is HK$702
HK$1,317 total
includes taxes & fees
15 Mar - 16 Mar
Blakley Hobbit Large Cabin
Terrace/patio

Apartment in Viola

Blakley Hobbit Small Cabin
7.8 out of 10, Good, (51 reviews)
"Enjoy our stay."
United States
Sondra M.
The price is HK$507
HK$947 total
includes taxes & fees
15 Mar - 16 Mar
Blakley Hobbit Small Cabin
Interior

Holiday Home in Westby

The Honey Haven
10.0 out of 10, Exceptional, (47 reviews)
"Quiet, clean, nestled in nature!"
United States
jim g.
The price is HK$1,249
HK$1,976 total
includes taxes & fees
25 Mar - 26 Mar
The Honey Haven
Smart TV, fireplace

Holiday Home in Viola

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is HK$1,405
HK$2,437 total
includes taxes & fees
2 Apr - 3 Apr
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Smart TV, fireplace, books, stereo

Cottage in Stoddard

Stylish 1 bedroom cottage along the Mississippi River
9.6 out of 10, Exceptional, (26 reviews)
"Very clean and well appointed. We enjoyed the convenient location to La Crosse and the many area hiking opportunities. It is on the highway and the railroad is right next to that, just so you know. It didn't bother us much, but we weren't there during the day much either."
United States
Michelle S.
The price is HK$688
HK$891 total
includes taxes & fees
5 Mar - 6 Mar
Stylish 1 bedroom cottage along the Mississippi River
Exterior

Cabin in Viroqua

Wagonwheel Ranch
9.8 out of 10, Exceptional, (18 reviews)
"Quiet location nice setting. Great host "
United States
Josh K.
The price is HK$2,178
HK$3,985 total
includes taxes & fees
10 Mar - 11 Mar
Wagonwheel Ranch
Exterior detail

Apartment in Viroqua

Cozy first floor at the heart of downtown Viroqua
10.0 out of 10, Exceptional, (54 reviews)
"Wonderful place! Clean, full of amenities, within walking distance to everything downtown has to offer."
United States
Alina L.
The price is HK$741
HK$1,392 total
includes taxes & fees
1 Apr - 2 Apr
Cozy first floor at the heart of downtown Viroqua
1 bedroom, WiFi, bed sheets

Apartment in Holy Trinity-Longfellow

Hidden Gem - 1BR/1Bath in Lax WI
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 HK$851
HK$1,292 total
includes taxes & fees
5 Mar - 6 Mar
Hidden Gem - 1BR/1Bath in Lax WI
Private kitchen

Holiday Home in Powell-Poage-Hamilton

Jake's Place
9.8 out of 10, Exceptional, (8 reviews)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is HK$1,171
HK$2,567 total
includes taxes & fees
5 Mar - 6 Mar
Jake's Place
Interior

Holiday Home in Holy Trinity-Longfellow

4 BR w/ Bluff Views | Snow-Dusted Escape
9.4 out of 10, Exceptional, (33 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 HK$1,113
HK$3,488 total
includes taxes & fees
5 Mar - 6 Mar
4 BR w/ Bluff Views | Snow-Dusted Escape
Property grounds

Camping in Viola

Blakley Hobbit Campground-RV spot #1
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 HK$390
HK$576 total
includes taxes & fees
9 Mar - 10 Mar
Blakley Hobbit Campground-RV spot #1
Smart TV, video games, table football, books

Cabin in Coon Valley

Valley Lodge w/Hot Tub & Arcade.
10.0 out of 10, Exceptional, (10 reviews)
"Great place to stay and explore the region. King bed was super comfy and the hot tub so relaxing. House was clean and very spacious- we loved it!"
United States
Kelly H.
Valley Lodge w/Hot Tub & Arcade.
Exterior

Holiday Home in Historic Downtown La Crosse

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
9.8 out of 10, Exceptional, (56 reviews)
"Loved the home! Perfect girls weekend!"
United States
Helen H.
The price is HK$1,440
HK$1,871 total
includes taxes & fees
5 Mar - 6 Mar
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Dining

Holiday Home in Cashton

Charming 3-bedroom townhome with WiFi, AC in adorable 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 HK$1,936
HK$3,280 total
includes taxes & fees
14 Mar - 15 Mar
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
5 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Viroqua

Garden Ridge Retreat- Farm Stay
10.0 out of 10, Exceptional, (8 reviews)
"Really enjoyed our stay. Great hosts no issues at all. Amazing views would definitely visit again "
United States
Joseph M.
The price is HK$1,517
HK$3,523 total
includes taxes & fees
8 Mar - 9 Mar
Garden Ridge Retreat- Farm Stay
Smart TV, fireplace, stereo

Cabin in Norwalk

Your adventure begins the second you arrive!
10.0 out of 10, Exceptional, (5 reviews)
"Easy check in. Beautiful cabin. We will be back for sure!"
United States
Dana S. S.
The price is HK$2,253
HK$2,715 total
includes taxes & fees
5 Mar - 6 Mar
Your adventure begins the second you arrive!
Smart TV, fireplace, DVD player, music library

Holiday Home in Cashton

Secluded Rustic Cabin
9.8 out of 10, Exceptional, (55 reviews)
"So relaxing and an amazing house"
United States
Ann W.
The price is HK$2,283
HK$3,833 total
includes taxes & fees
12 Mar - 13 Mar
Secluded Rustic Cabin
Outdoor dining

Holiday Home in Norwalk

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
9.6 out of 10, Exceptional, (23 reviews)
"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 HK$2,662
HK$5,551 total
includes taxes & fees
12 Mar - 13 Mar
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
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

Baymont by Wyndham La Crosse/Onalaska

Baymont by Wyndham La Crosse/Onalaska

10/10 Excellent
"The hotel could use some updating but it is clean and the staff is friendly. Housekeeping even cleaned our room and changed our towels after the first night without us asking. We’ve stayed here before and will again. Thank you! "
Sue 2-night trip
Posted 15 hours ago
Baymont by Wyndham La Crosse/Onalaska

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 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?

Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples: This holiday home rental outside of Portland is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

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 LaCrosse River 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.