Portland Vacation Rentals

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Our top choices for Portland vacation rentals

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
10.0 out of 10, Exceptional, (1 review)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
$171 nightly
The price is $180
May 22 - May 23
Total with taxes and fees
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

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.
$160 nightly
The price is $169
May 25 - May 26
Total with taxes and fees
Blakley Hobbit Large Cabin

Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.8 out of 10, Good, (52 reviews)
"Enjoy our stay."
United States
Sondra M.
$115 nightly
The price is $121
May 22 - May 23
Total with taxes and fees
Blakley Hobbit Small Cabin

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
9.0 out of 10, Wonderful, (12 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
$297 nightly
The price is $313
May 25 - May 26
Total with taxes and fees
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (28 reviews)
"Beautiful relaxing getaway!"
United States
Amanda M.
$278 nightly
The price is $293
May 28 - May 29
Total with taxes and fees
Your adventure begins the second you arrive!

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (49 reviews)
"Excellent stay. Clean with beautiful surroundings and a great dog to greet you."
United States
Jason B.
$240 nightly
The price is $253
May 25 - May 26
Total with taxes and fees
The Honey Haven

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.
$70 nightly
The price is $74
May 22 - May 23
Total with taxes and fees
Blakley Hobbit Campground-RV spot #1

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

Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Norwalk
9.6 out of 10, Exceptional, (23 reviews)
"Everyone had a great time!"
United States
Jim K.
$675 nightly
The price is $712
May 26 - May 27
Total with taxes and fees
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes

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.
$398 nightly
The price is $419
May 25 - May 26
Total with taxes and fees
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (5 reviews)
"Easy check in. Beautiful cabin. We will be back for sure!"
United States
Dana S. S.
$329 nightly
The price is $347
May 26 - May 27
Total with taxes and fees
Your adventure begins the second you arrive!

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, (56 reviews)
"Great convenience, quiet, well maintained, cute & cozy! Would definitely stay again! "
United States
Lynette W.
$178 nightly
The price is $198
May 27 - May 28
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
9.0 out of 10, Wonderful, (2 reviews)
"We had the pleasure of getting a little snow during our stay which was awesome.But the roads from the cabin were sloppy with the melt the following day and we had trouble getting out to go for a grocery run. Kirsty and Kyle were very helpful and were kind enough to bring us some coffee and flour. Really great folks and a very beautiful and private location. Great space to reset from reality. Highly recommend."
United States
Nick W.
$356 nightly
The price is $375
May 25 - May 26
Total with taxes and fees
Your adventure begins the second you arrive!

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (10 reviews)
"Just a quick get away for the weekend. Close access to local restaurants, breweries, beautiful landscape."
United States
Heidi C.
$329 nightly
The price is $347
May 26 - May 27
Total with taxes and fees
Your adventure begins the second you arrive!

#4 Blakley Hobbit Campground-Tent spot

#4 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (2 reviews)
"A great spot for a getaway weekend. 20 minutes to viroqua"
United States
Luke S.
$40 nightly
The price is $42
May 22 - May 23
Total with taxes and fees
#4 Blakley Hobbit Campground-Tent spot

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

“The Ridgeline” – Luxury private home, on 4 acres
Viroqua
$333 nightly
The price is $351
May 31 - Jun 1
Total with taxes and fees
“The Ridgeline” – Luxury private home, on 4 acres

#10 Blakley Hobbit Campground-Tent spot

#10 Blakley Hobbit Campground-Tent spot
Viola
10.0 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Huan B.
$40 nightly
The price is $42
May 22 - May 23
Total with taxes and fees
#10 Blakley Hobbit Campground-Tent spot

#3 Blakley Hobbit Campground-Tent spot

#3 Blakley Hobbit Campground-Tent spot
Viola
$40 nightly
The price is $42
May 22 - May 23
Total with taxes and fees
#3 Blakley Hobbit Campground-Tent spot

Blakley Hobbit Campground-RV spot #4

Blakley Hobbit Campground-RV spot #4
Viola
10.0 out of 10, Exceptional, (1 review)
"Lovely spot right on river. Trout fishing all around area."
United States
Brett
$70 nightly
The price is $74
May 22 - May 23
Total with taxes and fees
Blakley Hobbit Campground-RV spot #4

Secluded Rustic Cabin

Secluded Rustic Cabin
Cashton
9.8 out of 10, Exceptional, (55 reviews)
"The house and property were beautiful, we loved relaxing in the 3 seasons room and hot tub, enjoying the view of the fall colors, and getting away from it all. "
United States
Morgan K.
$466 nightly
The price is $491
May 25 - May 26
Total with taxes and fees
Secluded Rustic Cabin

#5 Blakley Hobbit Campground-Tent spot

#5 Blakley Hobbit Campground-Tent spot
Viola
$40 nightly
The price is $42
May 22 - May 23
Total with taxes and fees
#5 Blakley Hobbit Campground-Tent spot
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

Find out more about Portland

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 $169 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?

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 Elroy Sparta State Trail. Vernon Vineyards and LaCrosse River Trail 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.