A cityscape with a prominent domed building, a calm body of water reflecting the skyline, and a row of trees lining the waterfront.

Oregon Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oregon holiday rentals

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (203 reviews)
"Good location"
United States
ANCA
The price is NZ$211
includes taxes & fees
2 Dec - 3 Dec
The Dylin

2. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is NZ$389
includes taxes & fees
2 Dec - 3 Dec
Pool with Slide. Great for Business Travelers!

3. King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

4. Spacious 3-bedroom apartment in Downtown Stoughton

Spacious 3-bedroom apartment in Downtown Stoughton
Stoughton
The price is NZ$617
includes taxes & fees
2 Nov - 3 Nov
Spacious 3-bedroom apartment in Downtown Stoughton

5. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (58 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
The price is NZ$215
includes taxes & fees
8 Nov - 9 Nov
A Room with a View

6. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (56 reviews)
"Great and easy stay! The place was comfortable and inviting. Would stay again!"
United States
Taylor S.
The price is NZ$591
includes taxes & fees
30 Nov - 1 Dec
2 Bed, 2 Bath Apartment at Cannery Square

7. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great location - able to walk to many stores and restaurants. Spacious for a studio and very quiet."
United States
Martha T.
The price is NZ$463
includes taxes & fees
6 Nov - 7 Nov
Studio Apartment at Cannery Square

8. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
The price is NZ$465
includes taxes & fees
2 Nov - 3 Nov
Charming Downtown Two Bedroom w/ Fireplace

9. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
The price is NZ$323
includes taxes & fees
29 Nov - 30 Nov
King Suite | Free Breakfast. Pool and Hot Tub

10. Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful place, great stay."
United States
Thomas D.
The price is NZ$454
includes taxes & fees
2 Nov - 3 Nov
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

11. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is NZ$430
includes taxes & fees
3 Nov - 4 Nov
Studio Apartment at Cannery Square

12. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (34 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is NZ$427
includes taxes & fees
21 Nov - 22 Nov
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

13. Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is NZ$449
includes taxes & fees
2 Nov - 3 Nov
Escape to tranquility – your countryside haven, and at times with a horse or two

14. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (47 reviews)
"Great stay! Very close to everything downtown."
United States
Garrett M.
The price is NZ$542
includes taxes & fees
16 Nov - 17 Nov
Doty ★ Walk to Everything -Hotel Quality- Downtown

15. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (31 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is NZ$573
includes taxes & fees
2 Nov - 3 Nov
2 Bed, 2 Bath Apartment at Cannery Square

16. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Everything was very nice"
United States
Anonymous traveller
The price is NZ$782
includes taxes & fees
16 Nov - 17 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

17. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
The price is NZ$506
includes taxes & fees
30 Nov - 1 Dec
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

18. New Luxury & Spacious House in the Heart of Janesville

New Luxury & Spacious House in the Heart of Janesville
Janesville
8.8 out of 10, Excellent, (12 reviews)
"Great location for downtown Janesville "
United States
Tim M.
New Luxury & Spacious House in the Heart of Janesville

19. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (15 reviews)
"We love this property on the Sugar River. Very spacious, rustic but with all the modern amenities. Beautiful view of the water and lots of wildlife in area. "
United States
Lisa and Peter R.
The price is NZ$1,292
includes taxes & fees
5 Nov - 6 Nov
Lake Cabin | Sauna · River · Game Room

20. Blue Lakeview Home

Blue Lakeview Home
Edgerton
The price is NZ$461
includes taxes & fees
29 Nov - 30 Nov
Blue Lakeview Home
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oregon Hotel Reviews

Find out more about Oregon

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oregon holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oregon. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oregon. Seeing all the best attractions is bound to make you fall in love with Oregon. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oregon short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Oregon?

Yes, there are holiday rentals close to the most popular sights in Oregon, or you can select a more secluded option if you're looking for a relaxing stay. Oregon is known for its golf courses.

What are some of the best holiday rentals that Oregon has to offer?

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail: This holiday home rental outside of Oregon is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Oregon?

Choose from 5 Expedia holiday rentals in Oregon for a memorable holiday.

What can I see and do in Oregon?

Explore the area and family-friendly sights such as Verona Ice Arena, or get out into nature at a spot like Lake Waubesa. In the wider area, you’ll find Legend at Bergamont and Alliant Energy Center.

What are holiday rentals like in Oregon?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oregon. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.