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Portland Holiday Rentals

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Our top choices for Portland holiday rentals

Blakley Hobbit Large Cabin

Blakley Hobbit Large Cabin
Viola
8.0 out of 10, Very good, (43 reviews)
"Very peaceful, charming rustic cabin. I highly recommend and we plan to come back. "
United States
Jonathan C.
The price is NZ$299
includes taxes & fees
30 June - 1 July
Blakley Hobbit Large Cabin

Blakley Hobbit Small Cabin

Blakley Hobbit Small Cabin
Viola
7.8 out of 10, Good, (55 reviews)
"Enjoy our stay."
United States
Sondra M.
The price is NZ$215
includes taxes & fees
14 July - 15 July
Blakley Hobbit Small Cabin

#6 Blakley Hobbit Campground-Tent spot

#6 Blakley Hobbit Campground-Tent spot
Viola
The price is NZ$75
includes taxes & fees
29 June - 30 June
#6 Blakley Hobbit Campground-Tent spot

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, (2 reviews)
"Great host, beautiful property! Would definitely go back!"
United States
Bridgette B.
The price is NZ$340
includes taxes & fees
29 June - 30 June
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.

Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (29 reviews)
"Very secluded. Perfect for a weekend away. "
United States
Mathew D.
The price is NZ$380
includes taxes & fees
30 June - 1 July
Your adventure begins the second you arrive!

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (51 reviews)
"Excellent stay. Clean with beautiful surroundings and a great dog to greet you."
United States
Jason B.
The price is NZ$447
includes taxes & fees
29 June - 30 June
The Honey Haven

Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua
Viroqua
9.8 out of 10, Exceptional, (58 reviews)
"Nice place to stay right in town perfect for a couple "
United States
Pete G.
The price is NZ$352
includes taxes & fees
7 July - 8 July
Cozy first floor at the heart of downtown Viroqua

Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Peaceful Country Comfort W Panoramic Views of Big Creek Valley
Sparta
10.0 out of 10, Exceptional, (146 reviews)
"Our host was so welcoming, their property so beautiful and peaceful. "
United States
Wendy H.
The price is NZ$322
includes taxes & fees
29 June - 30 June
Peaceful Country Comfort W Panoramic Views of Big Creek Valley

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 NZ$433
includes taxes & fees
29 June - 30 June
Place of Peace - the Artist's Refuge

Breezy 4BR | Steps to UW Campus

Breezy 4BR | Steps to UW Campus
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (37 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 NZ$834
includes taxes & fees
29 June - 30 June
Breezy 4BR | Steps to UW Campus

Cozy 5BR Duplex by Mayo, 50-ft Parking

Cozy 5BR Duplex by Mayo, 50-ft Parking
Holy Trinity-Longfellow
The price is NZ$717
includes taxes & fees
20 July - 21 July
Cozy 5BR Duplex by Mayo, 50-ft Parking

The Hilltop

The Hilltop
Norwalk
10.0 out of 10, Exceptional, (11 reviews)
"Just a quick get away for the weekend. Close access to local restaurants, breweries, beautiful landscape."
United States
Heidi C.
The price is NZ$634
includes taxes & fees
29 June - 30 June
The Hilltop

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, (14 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is NZ$546
includes taxes & fees
29 June - 30 June
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

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, (69 reviews)
"Great communication with hostBeautiful historic home. Wonderful place to stay with a group. "
United States
Melissa W.
The price is NZ$427
includes taxes & fees
1 July - 2 July
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Garden Ridge Retreat- Farm Stay

Garden Ridge Retreat- Farm Stay
Viroqua
10.0 out of 10, Exceptional, (13 reviews)
"Was a great place for our annual 4 couple get together. Host gave us a tour of their farm and there was a wonderful selection of their own farm raised pork, beef and strawberries."
United States
Kurt F.
The price is NZ$979
includes taxes & fees
6 July - 7 July
Garden Ridge Retreat- Farm Stay

Secluded Rustic Cabin

Secluded Rustic Cabin
Cashton
9.8 out of 10, Exceptional, (55 reviews)
"What a wonderful property! "
United States
Becky K.
The price is NZ$850
includes taxes & fees
29 June - 30 June
Secluded Rustic Cabin

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 NZ$683
includes taxes & fees
12 July - 13 July
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton

#7 Blakley Hobbit Campground-Tent spot

#7 Blakley Hobbit Campground-Tent spot
Viola
The price is NZ$75
includes taxes & fees
29 June - 30 June
#7 Blakley Hobbit Campground-Tent spot

Blakley Hobbit Campground-RV spot #2

Blakley Hobbit Campground-RV spot #2
Viola
The price is NZ$131
includes taxes & fees
29 June - 30 June
Blakley Hobbit Campground-RV spot #2

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, (24 reviews)
"Everyone had a great time!"
United States
Jim K.
The price is NZ$1,237
includes taxes & fees
29 June - 30 June
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

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$215 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?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This holiday home rental outside of 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 that 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. Branches Winery and Vernon Vineyards 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.