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
 Hidden Gem SLEEPS 10+! Ask about Mon-Thurs SPECIAL! Stay 2 nights, get one free

Hidden Gem SLEEPS 10+! Ask about Mon-Thurs SPECIAL! Stay 2 nights, get one free

Rockford
The price is AU$720 per night from 27 Mar to 28 Mar
AU$720
includes taxes & fees
27 Mar - 28 Mar
With a stay at this vacation home in Rockford, you'll be within a 5-minute drive of SwedishAmerican Hospital and Jefferson Street Bridge.
Hidden Gem SLEEPS 10+! Ask about Mon-Thurs SPECIAL! Stay 2 nights, get one free
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
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
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
The price is AU$1,610 per night from 17 Mar to 18 Mar
AU$1,610
includes taxes & fees
17 Mar - 18 Mar
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
3 bedroom house with a nature backyard!

3 bedroom house with a nature backyard!

Rockford
With a stay at this vacation home in Rockford, you'll be within a 15-minute walk of Sarbrook Park and Don Schmid Park.
3 bedroom house with a nature backyard!
Relaxing ranch in NE Rockford

Relaxing ranch in NE Rockford

Rockford
With a stay at this vacation home in Rockford, you'll be within a 5-minute drive of Anderson Japanese Gardens and SwedishAmerican Hospital.
Relaxing ranch in NE Rockford
NEW! Family-friendly cabin-style home w/ gameroom + gym

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

Rockford
The price is AU$598 per night from 31 Mar to 1 Apr
AU$598
includes taxes & fees
31 Mar - 1 Apr
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
Spacious 5-bedroom house with AC and WiFi in brilliant Machesney Park

Spacious 5-bedroom house with AC and WiFi in brilliant Machesney Park

Rockford
The price is AU$823 per night from 15 Apr to 16 Apr
AU$823
includes taxes & fees
15 Apr - 16 Apr
Located in Rockford, this vacation home is a 3-minute drive from Anderson Japanese Gardens and 7 minutes from Veterans Memorial Hall.
Spacious 5-bedroom house with AC and WiFi in brilliant Machesney Park
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
58 Holiday Homes
Lowest Price
AU$122
Highest Price
AU$1,610
Popular accommodation
Riverfront cabin on Rock River, Hidden Gem SLEEPS 10+! Ask about Mon-Thurs SPECIAL! Stay 2 nights, get one free, Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing, This 4 BR Home With A Great Game Room Is Located Close To Shopping And Dining, Father of the Bride Private Estate with Pool & Hot Tub - Sleeps 25, 3 bedroom house with a nature backyard!, Relaxing ranch in NE Rockford, NEW! Family-friendly cabin-style home w/ gameroom + gym, Spacious 5-bedroom house with AC and WiFi in brilliant Machesney Park

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$124 per night from 25 Mar to 26 Mar
AU$124
includes taxes & fees
25 Mar - 26 Mar
Located in Oregon, Paddle Wheel Inn is within a 15-minute drive of Lowden State Park and Castle Rock State Park.
Paddle Wheel Inn
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
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$122 per night from 17 Mar to 18 Mar
AU$122
includes taxes & fees
17 Mar - 18 Mar
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
Save an average of 15% on thousands of hotels when you're signed in
ROCK RIVER HIDEAWAY Outdoor Activities, Grill Fire Pit, Pet Friendly with fee

ROCK RIVER HIDEAWAY Outdoor Activities, Grill Fire Pit, Pet Friendly with fee

Oregon
Located in Oregon, this vacation home is on the waterfront, a 3-minute drive from Castle Rock State Park and 5 minutes from Village Way Dog Park.
ROCK RIVER HIDEAWAY Outdoor Activities, Grill Fire Pit, Pet Friendly with fee
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.