Book Holiday Homes in Oregon

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Oregon

Riverfront cabin on Rock River

Riverfront cabin on Rock River

Rockford
Located in Rockford, this vacation home is on the waterfront, within a 5-minute drive of Barnstormer Distillery and Wayside Park.
Riverfront cabin on Rock River
Cozy home in Rockford 
Sleeps 8

Cozy home in Rockford Sleeps 8

Rockford
With a stay at this vacation home in Rockford, you'll be within a 5-minute drive of Wesley Willows Town Center and Javon Bea Hospital - Rockton.
Cozy home in Rockford Sleeps 8
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Oregon
Located in Oregon, this vacation home is a 3-minute drive from Castle Rock State Park and 6 minutes from Village Way Dog Park.
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
Save an average of 15% on thousands of hotels when you're signed in
Historic downtown home w/ playroom pool table, 2 doors from river

Historic downtown home w/ playroom pool table, 2 doors from river

Rockford
When you stay at this vacation home in Rockford, you'll be on a river, within a 10-minute walk of Burpee Museum of Natural History and Rockford Art Museum.
Historic downtown home w/ playroom pool table, 2 doors from river
This 4 BR Home With A Great Game Room Is Located Close To Shopping And Dining

This 4 BR Home With A Great Game Room Is Located Close To Shopping And Dining

Rockford
With a stay at this vacation home in Rockford, you'll be within a 5-minute drive of The Cherry Bowl and Weis Morris DaySpa Salon.
This 4 BR Home With A Great Game Room Is Located Close To Shopping And Dining
Rockford Cascade Getaway

Rockford Cascade Getaway

2 out of 5
Rockford
Located in Rockford, this vacation home is within a 10-minute drive of Don Schmid Park and Kishwaukee River Forest Preserve.
Rockford Cascade Getaway
Tranquil Escape Indoor Pool Spa Arcade

Tranquil Escape Indoor Pool Spa Arcade

Rockford
Located in Rockford, this vacation home is a 3-minute drive from Anderson Japanese Gardens and 6 minutes from Jefferson Street Bridge.
Tranquil Escape Indoor Pool Spa Arcade
Father of the Bride Private Estate with Pool & Hot Tub - Sleeps 25

Father of the Bride Private Estate with Pool & Hot Tub - Sleeps 25

Rockford
With a stay at this vacation home in Rockford, you'll be within a 5-minute drive of Midway Village & Museum Center and Midway Village Museum.
Father of the Bride Private Estate with Pool & Hot Tub - Sleeps 25
NEW! Family-friendly cabin-style home w/ gameroom + gym

NEW! Family-friendly cabin-style home w/ gameroom + gym

Rockford
The price is AU$566 per night from 9 Dec to 10 Dec
AU$566
includes taxes & fees
9 Dec - 10 Dec
Located in Rockford, this vacation home is within a 5-minute drive of Anderson Japanese Gardens and OSF Saint Anthony Medical Center.
NEW! Family-friendly cabin-style home w/ gameroom + gym
Don't see what you're looking for?
See all available properties in Oregon
View all properties
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.

Oregon Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oregon vacation homes are the perfect way for you to wing it.

Holiday houses in Oregon let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oregon in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oregon adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oregon with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oregon vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oregon Holiday Homes essential information

Accommodation
50 Holiday Homes
Lowest Price
AU$121
Highest Price
AU$566
Popular accommodation
Riverfront cabin on Rock River, Cozy home in Rockford Sleeps 8 , Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing, Historic downtown home w/ playroom pool table, 2 doors from river, This 4 BR Home With A Great Game Room Is Located Close To Shopping And Dining, Rockford Cascade Getaway, Tranquil Escape Indoor Pool Spa Arcade, Father of the Bride Private Estate with Pool & Hot Tub - Sleeps 25, NEW! Family-friendly cabin-style home w/ gameroom + gym

Top trending hotels in Oregon

Paddle Wheel Inn

Paddle Wheel Inn

2 out of 5
1457 IL Rt 2 North, Oregon, IL
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 26 Nov to 27 Nov
AU$121
includes taxes & fees
26 Nov - 27 Nov
Located in Oregon, Paddle Wheel Inn is within a 15-minute drive of Lowden State Park and Castle Rock State Park.
Paddle Wheel Inn
Chateau Lodge

Chateau Lodge

2 out of 5
1326 IL Route 2 N., Oregon, IL
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 26 Nov to 27 Nov
AU$138
includes taxes & fees
26 Nov - 27 Nov
Located in Oregon, Chateau Lodge is in the historical district, a 2-minute drive from Conover Square Mall and 9 minutes from Lowden State Park.
Chateau Lodge
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing

Oregon
Located in Oregon, this vacation home is a 3-minute drive from Castle Rock State Park and 6 minutes from Village Way Dog Park.
Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing
Save an average of 15% on thousands of hotels when you're signed in
Unique Victorian Cottage Close to Town

Unique Victorian Cottage Close to Town

Oregon
When you stay at this cottage in Oregon, you'll be on a river, within a 5-minute drive of Conover Square Mall and Lowden State Park.
Unique Victorian Cottage Close to Town
Don't see what you're looking for?
See all available properties in Oregon
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.