Holiday Rentals in Portland

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Holiday Rentals in Portland

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

10.0 out of 10, Exceptional, (39)
"Beautiful house and wonderful host. Close to downtown where all the fun is!"
The price is €393
includes taxes & fees
1 Sept - 2 Sept
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

Blakley Hobbit Small Cabin

7.8 out of 10, Good, (44)
"Easiest check-in, perfectly met expectations and needs."
The price is €110
includes taxes & fees
3 Aug - 4 Aug
Blakley Hobbit Small Cabin

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

9.8 out of 10, Exceptional, (141)
"Very near cabin ideally located for trout fushing. Very accurately described and the communication by the host was very good."
Fly Fishing in the Driftless Region - Bishop Creek Cabin with a View

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

10.0 out of 10, Exceptional, (230)
"Great place for a weekend getaway!"
Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (29)
"House was amazing and was exactly as advertised. Would definitely stay again."
The price is €205
includes taxes & fees
13 Aug - 14 Aug
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

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

8.8 out of 10, Excellent, (85)
"We were celebrating my sons 18th birthday with some of his friends. Everything worked out great, except there was hardly any Wi-Fi. Otherwise, everything was clean and spacious. "
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

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

10.0 out of 10, Exceptional, (253)
"We had a wonderful stay. Great hosts and a perfect cabin."
Arcadian Cabin at Bishop Branch, creek-front, public land access, great location

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

10.0 out of 10, Exceptional, (143)
"3 couples enjoying a weekend away :) "
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Secluded Rustic Cabin

9.8 out of 10, Exceptional, (48)
"Very nicely secluded. Would stay again."
The price is €393
includes taxes & fees
3 Aug - 4 Aug
Secluded Rustic Cabin

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

9.0 out of 10, Wonderful, (4)
"Quiet Place"
The price is €282
includes taxes & fees
2 Aug - 3 Aug
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Your Home Away From Home

9.6 out of 10, Exceptional, (144)
"Beautiful location and private area. Loved the little stream on the property!"
Your Home Away From Home

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

10.0 out of 10, Exceptional, (4)
"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!

Marina getaway located on the back sloughs of the mighty Mississippi.

10.0 out of 10, Exceptional, (66)
"We had a great stay! Perfect quiet place near everything!"
Marina getaway located on the back sloughs of the mighty Mississippi.

Peaceful Country Comfort W Panoramic Views of Big Creek Valley

10.0 out of 10, Exceptional, (131)
"We biked the Elroy Sparta Bike trail. Great location for that in an absolute beautiful location! Very clean and 2 nice bathrooms. Would stay again for sure!"
Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Cozy Amish built cabin in the heart of the Kickapoo Valley Reserve State Park.

9.4 out of 10, Exceptional, (11)
"We stayed in Brian’s cabin for a family reunion in La Farge and had a wonderful stay. The cabin was spacious, cozy, clean, and tidy. Brian was also very friendly and helpful when he stopped by to welcome us and tell us all about the area. Lastly, I loved all the beds in the cabin - plenty of room for our big crew to sleep comfortably and soundly. Would love to come back soon."
Cozy Amish built cabin in the heart of the Kickapoo Valley Reserve State Park.

'RiverSong' Waterfront La Crosse Home w/ Dock

10.0 out of 10, Exceptional, (78)
"An exceptional experience!"
'RiverSong' Waterfront La Crosse Home w/ Dock

Country Living at its Finest

9.8 out of 10, Exceptional, (210)
"Lovely, well appointed and clean cabin in the woods. It was difficult to find on gps and the internet connections were a bit unclear. However, the host came over quickly and helped to get things operating. They were very friendly and eager to address our questions. Lovely, quiet and serene surroundings. Would definitely return."
Country Living at its Finest

Cabin in Beautiful Timber Coulee

10.0 out of 10, Exceptional, (87)
"Awesome place! Would definitely stay again. Such a cool location!!! We had a family of otters hang out with us all weekend."
Cabin in Beautiful Timber Coulee

Jake's Place

9.6 out of 10, Exceptional, (5)
"Was so much better than the large groups of people at motels and quit"
The price is €262
includes taxes & fees
26 Aug - 27 Aug
Jake's Place

Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

9.8 out of 10, Exceptional, (11)
"Home is located in a great area with all the amenities needed. Very nice home!"
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse
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

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?

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!: This holiday home rental outside of Portland offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.