Book Holiday Homes in Oregon

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Featured Holiday Homes in Oregon

ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

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 Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
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
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!
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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
Fish, Hike & Boat: Modern Rock Falls Home

Fish, Hike & Boat: Modern Rock Falls Home

Rock Falls
With a stay at this vacation home in Rock Falls, you'll be within a 10-minute drive of Westwood Tennis Center and Sinnissippi Park.
Fish, Hike & Boat: Modern Rock Falls Home
Duplex overlooking Rock River

Duplex overlooking Rock River

Byron
Located in Byron, this vacation home is on a river, within a 10-minute drive of Stillman's Defeat Memorial Site and Wayside Park.
Duplex overlooking Rock River
Huge 2+BR Near Hospitals & Aerospace: Lives like a 3 bedroom with addtl spaces

Huge 2+BR Near Hospitals & Aerospace: Lives like a 3 bedroom with addtl spaces

Rockford
Located in Rockford, this vacation home is within a 5-minute drive of Midway Village & Museum Center and Weis Morris DaySpa Salon.
Huge 2+BR Near Hospitals & Aerospace: Lives like a 3 bedroom with addtl spaces
 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
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
Take Dad Fishing! Available for Father’s Day!

Take Dad Fishing! Available for Father’s Day!

Rockford
Located in Rockford, this vacation home is on the waterfront, within a 10-minute drive of Boylan Tennis Center and Javon Bea Hospital - Rockton.
Take Dad Fishing! Available for Father’s Day!
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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
73 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night, Riverfront cabin on Rock River, 3 bedroom house with a nature backyard!, Getaway Cabin on the Rock River, enjoy kayaking, canoeing and fishing, Fish, Hike & Boat: Modern Rock Falls Home, Duplex overlooking Rock River, Huge 2+BR Near Hospitals & Aerospace: Lives like a 3 bedroom with addtl spaces, Hidden Gem SLEEPS 10+! Ask about Mon-Thurs SPECIAL! Stay 2 nights, get one free, Take Dad Fishing! Available for Father’s Day!

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
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
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
ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

ROCK RIVER HIDEAWAY Grill, Fire Pit, Pet Friendly with fee of 30.00 per night

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 Grill, Fire Pit, Pet Friendly with fee of 30.00 per night
Save an average of 15% on thousands of hotels when you're signed in
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
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.

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^Subject to availability and chosen travel dates.