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Portland Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Portland vacation rentals

Exterior

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 SAR 507
SAR 717 total
includes taxes & fees
23 Jun - 24 Jun
Private cabin on the beautiful Kickapoo River Valley near Wildcat Mountain Park.
Exterior

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 SAR 338
SAR 634 total
includes taxes & fees
29 Jun - 30 Jun
Blakley Hobbit Large Cabin
Terrace/patio

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 SAR 244
SAR 455 total
includes taxes & fees
28 Jun - 29 Jun
Blakley Hobbit Small Cabin
Interior

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (50 reviews)
"Excellent stay. Clean with beautiful surroundings and a great dog to greet you."
United States
Jason B.
The price is SAR 601
SAR 950 total
includes taxes & fees
25 Jun - 26 Jun
The Honey Haven
Interior

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 SAR 664
SAR 804 total
includes taxes & fees
23 Jun - 24 Jun
Your adventure begins the second you arrive!
Property grounds

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, (145 reviews)
"Our host was so welcoming, their property so beautiful and peaceful. "
United States
Wendy H.
The price is SAR 571
SAR 689 total
includes taxes & fees
23 Jun - 24 Jun
Peaceful Country Comfort W Panoramic Views of Big Creek Valley
Exterior detail

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 SAR 402
SAR 728 total
includes taxes & fees
23 Jun - 24 Jun
Cozy first floor at the heart of downtown Viroqua
Property grounds

#6 Blakley Hobbit Campground-Tent spot

#6 Blakley Hobbit Campground-Tent spot
Viola
The price is SAR 75
SAR 158 total
includes taxes & fees
23 Jun - 24 Jun
#6 Blakley Hobbit Campground-Tent spot
Smart TV, fireplace, stereo

The Incline

The Incline
Norwalk
10.0 out of 10, Exceptional, (5 reviews)
"This place is a perfect couples getaway! "
United States
Kurt T.
The price is SAR 1,126
SAR 1,358 total
includes taxes & fees
23 Jun - 24 Jun
The Incline
Smart TV, fireplace

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 SAR 676
SAR 1,176 total
includes taxes & fees
23 Jun - 24 Jun
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Exterior

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 SAR 693
SAR 904 total
includes taxes & fees
23 Jun - 24 Jun
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Smart TV, fireplace, DVD player, music library

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 SAR 1,098
SAR 1,832 total
includes taxes & fees
23 Jun - 24 Jun
Secluded Rustic Cabin
Living area

Cozy 5BR Duplex by Mayo, 50-ft Parking

Cozy 5BR Duplex by Mayo, 50-ft Parking
Holy Trinity-Longfellow
The price is SAR 564
SAR 1,499 total
includes taxes & fees
30 Jun - 1 Jul
Cozy 5BR Duplex by Mayo, 50-ft Parking
Fireplace

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 SAR 1,107
SAR 2,139 total
includes taxes & fees
6 Jul - 7 Jul
Garden Ridge Retreat- Farm Stay
Outdoor dining

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 SAR 1,280
SAR 2,673 total
includes taxes & fees
25 Jun - 26 Jun
Spacious & secluded grand home near Kickapoo River, Bike Trails, & ATV routes
Dining

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 SAR 887
SAR 1,522 total
includes taxes & fees
10 Jul - 11 Jul
Charming 3-bedroom townhome with WiFi, AC in adorable Cashton
Property grounds

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
The price is SAR 188
SAR 277 total
includes taxes & fees
23 Jun - 24 Jun
Blakley Hobbit Campground-RV spot #4
Property grounds

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.
The price is SAR 188
SAR 277 total
includes taxes & fees
23 Jun - 24 Jun
Blakley Hobbit Campground-RV spot #1
Property grounds

Blakley Hobbit Campground-RV spot #2

Blakley Hobbit Campground-RV spot #2
Viola
The price is SAR 188
SAR 277 total
includes taxes & fees
23 Jun - 24 Jun
Blakley Hobbit Campground-RV spot #2
Property grounds

#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.
The price is SAR 75
SAR 158 total
includes taxes & fees
23 Jun - 24 Jun
#10 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

AmericInn by Wyndham Viroqua

AmericInn by Wyndham Viroqua

8/10 Good
"For a hotel in this area, it was well kept, the staff at the front desk were helpful and friendly. However the room wasn’t that clean. Stains on the walls, mold on the curtains cobwebs by the door."
Brandi 1-night trip
Posted 6 hours ago
AmericInn by Wyndham Viroqua

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 Norskedalen Nature and Heritage Center. Branches Winery and Elroy Sparta State 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.