Portland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Portland

Blakley Hobbit Large Cabin

Viola
8.2 out of 10, Very good, (39)
"We loved this spot and will definitely be booking it again. The cabin has everythinf you need for a quick easy vacation. "
United States
Justine C.
The price is NZ$297
includes taxes & fees
19 Nov - 20 Nov
Blakley Hobbit Large Cabin

Blakley Hobbit Small Cabin

Viola
7.8 out of 10, Good, (51)
"Great"
United States
Renee F.
The price is NZ$214
includes taxes & fees
22 Nov - 23 Nov
Blakley Hobbit Small Cabin

Blakley Hobbit Campground-Tent spot #9

Viola
10.0 out of 10, Exceptional, (1)
The price is NZ$74
includes taxes & fees
13 Dec - 14 Dec
Blakley Hobbit Campground-Tent spot #9

The Honey Haven

Westby
10.0 out of 10, Exceptional, (46)
"The property and our stay were amazing! We had a great get away and would definitely plan to be back"
United States
Kerri K.
The price is NZ$444
includes taxes & fees
15 Dec - 16 Dec
The Honey Haven

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

Viola
9.6 out of 10, Exceptional, (7)
"Quiet Place"
United States
Zofia Z.
The price is NZ$551
includes taxes & fees
27 Nov - 28 Nov
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Place of Peace - the Artist's Refuge

La Farge
10.0 out of 10, Exceptional, (13)
"We had a lovely, peaceful stay here. The house is clean, uncluttered, and open-feeling, and the view outside is beautiful. There were small luxurious touches throughout that made this place feel loved. The location was perfect for river trips on the Kickapoo. "
United States
Catherine W.
The price is NZ$434
includes taxes & fees
27 Nov - 28 Nov
Place of Peace - the Artist's Refuge

Cozy first floor at the heart of downtown Viroqua

Viroqua
10.0 out of 10, Exceptional, (52)
"Needed a place to stay for the weekend and this was a great accommodation. "
United States
Carla Sam S.
The price is NZ$314
includes taxes & fees
4 Dec - 5 Dec
Cozy first floor at the heart of downtown Viroqua

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

Norwalk
10.0 out of 10, Exceptional, (17)
"Our cabin was very clean, everything was where it was easy to find. The host was every kind and courteous. "
United States
Christina k.
The price is NZ$516
includes taxes & fees
17 Nov - 18 Nov
Quaint cabin overlooking the creek below and wetlands in the valley basin.

Jake's Place

Powell-Poage-Hamilton
9.8 out of 10, Exceptional, (8)
"Was so much better than the large groups of people at motels and quit"
United States
Jimmy S.
The price is NZ$520
includes taxes & fees
15 Dec - 16 Dec
Jake's Place

The best place for star gazing all night.

Norwalk
10.0 out of 10, Exceptional, (9)
"Very cozy get-away for a romantic night-in with the wife- perfectly set up for couples- the hot tub is amazing! Can't hear or see any neighbors or traffic- that was a plus for us."
United States
Ben D.
The price is NZ$614
includes taxes & fees
16 Nov - 17 Nov
The best place for star gazing all night.

Modern Mid-Century Home Near UW

Holy Trinity-Longfellow
9.2 out of 10, Wonderful, (32)
"Lovely atmosphere- great location. It was perfect for our family getaway to visit our son in college."
United States
Lynn M.
Modern Mid-Century Home Near UW

Blakley Hobbit Campground-RV spot #4

Viola
10.0 out of 10, Exceptional, (1)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
The price is NZ$130
includes taxes & fees
16 Nov - 17 Nov
Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-Tent spot #4

Viola
10.0 out of 10, Exceptional, (2)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
The price is NZ$74
includes taxes & fees
27 Nov - 28 Nov
Blakley Hobbit Campground-Tent spot #4

Large home space minutes from La Crosse

2.0 star property
Onalaska
The price is NZ$278
includes taxes & fees
9 Dec - 10 Dec
Large home space minutes from La Crosse

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

Norwalk
9.6 out of 10, Exceptional, (22)
"We had a wonderful time having a family gathering at this beautiful manor in a breathtaking setting! Thanks Paula!"
United States
John G.
The price is NZ$1,395
includes taxes & fees
17 Nov - 18 Nov
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

Blakley Hobbit Campground-Tent spot #10

Viola
10.0 out of 10, Exceptional, (2)
"The tent sites are right along the river. Not all of them have a fire pit, picnic table or grill but this is a lovely quiet serene spot to camp. "
United States
Deborah S.
The price is NZ$74
includes taxes & fees
16 Nov - 17 Nov
Blakley Hobbit Campground-Tent spot #10

Blakley Hobbit Campground-Tent spot #3

Viola
The price is NZ$74
includes taxes & fees
27 Nov - 28 Nov
Blakley Hobbit Campground-Tent spot #3

Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

2.0 star property
Cashton
9.0 out of 10, Wonderful, (2)
"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 NZ$739
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

Blakley Hobbit Campground-RV spot #1

Viola
9.0 out of 10, Wonderful, (2)
"Come up several times a year to this location nice mowed grass and close to river."
United States
Paul K.
The price is NZ$130
includes taxes & fees
16 Nov - 17 Nov
Blakley Hobbit Campground-RV spot #1
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$214 per night. Entering your travel dates in the search wizard you might find 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 Elroy Sparta State Trail. Branches Winery 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.