Photo by Timothy Kilkenny

Holiday Rentals in Oregon

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Holiday Rentals in Oregon

Property grounds
Cozy cottage retreat that’s perfect for recharging.
10.0 out of 10, Exceptional, (35)
"Stayed with 3 other adult friends. Location was secluded, quiet and definitely felt cabin-y. The huge yard was perfect for lawn games and sitting by the fire. We enjoyed how many places there were to sit, inside and out. Sleeping arrangements were great and the cabin was very well suited for hosting guests. Little things like sunscreen that we had forgotten were a nice touch. The river was a little off color. Some of our group swam but I wouldn’t book the place with intentions of being in the...
Cozy cottage retreat that’s perfect for recharging.
Fridge, microwave, oven, stovetop
Legacy Guest House , Mount Horeb WI
10.0 out of 10, Exceptional, (36)
"Nice place to stay"
Legacy Guest House , Mount Horeb WI
Property grounds
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (80)
"Everything was absolutely great! Location was perfect, lots of good restaurants and shopping near the house. Beautiful scenery and tranquil setting for relaxing. House was just as advertised and had everything we needed. Hosts are amazing and so kind! You’ll love the visits from their pups! Highly recommend!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
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Fridge, microwave, oven, stovetop
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (136)
"We rented this place to visit family in Madison and attend a ren faire. It was great as we were looking for a small place with a full kitchen to cook. Neat touches with the Alexa with song and light recommendations. We enjoyed the living room white board - played lots of Pictionary. Our group was myself, my daughter, and my sister. The basement den made a great third bedroom. I might recommend a pull out couch."
Amazing townhouse, amazing attractions, amazing city!
1 bedroom, free WiFi, bed sheets
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (10)
"Cute, cozy, and comfortable. Located in a beautiful peaceful setting. Host had a-lot of little extras available to us . Host was very helpful and accommodating. Sue H"
The price is €123
per night
27 May - 28 May
Enjoy Nature with Full Comfort!
Outdoor dining
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
10.0 out of 10, Exceptional, (132)
"We loved our stay. The house was comfortable and clean. It had all the amenities. The location was spectacular, and the backyard was super peaceful. Joan was a great host and communication was easy. There are three bedrooms for six people and a full-size futon, which is great for our group of 6."
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
Exterior
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (187)
"This was our first experience renting this home & we're definitely booking this home again next year. Everything from very attentive, kind renters, too extremely clean & renovated home, extremely comfortable beds & pillows. Not to mention the gorgeous & relaxing back yard. Perfect place to stay, for sure"
A Pleasant Retreat- No Cleaning Fee & New Discounts
On the beach
Madison & ~UW~-Madison Area Lakefront Home
9.8 out of 10, Exceptional, (165)
"The cottage is clean and well stocked for a long weekend. The view of the lake is beautiful, and I'm sure it's even better in the warm months. We had everything we needed. Great little house for a long weekend."
Madison & ~UW~-Madison Area Lakefront Home
Property grounds
Lakefront Home w/ Gorgeous Sunsets, Kayaks, & Pier
9.8 out of 10, Exceptional, (7)
"This wonderful lake home far exceeded our expectations !!!! Beautifully decorated, extremely inviting and extremely clean….. We will be back !!!"
Lakefront Home w/ Gorgeous Sunsets, Kayaks, & Pier
Fridge, microwave, stovetop, coffee/tea maker
Waterfront Lake Koshkonong Home w/ Pier & Fire Pit
9.8 out of 10, Exceptional, (71)
"Everything as listed. The house was clean. Great stay."
Waterfront Lake Koshkonong Home w/ Pier & Fire Pit
Property grounds
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
10.0 out of 10, Exceptional, (17)
"Our stay at the Pink Acorn was amazing! Kelly truly makes her guests feel welcome. She left a sweet note and lovely treats. The house is stocked with everything you need and was exceptionally clean. The beds are super comfortable and have nice cozy blankets. Am added bonus was seeing rabbits and chipmunks in the backyard. Kelly leaves directions to walk to the beach around the corner and it’s a must do…and make sure to grab some ice cream at the shop across from the park."
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Fridge, microwave, oven, stovetop
Newly updated water retreat. PONTOON for rent, FREE golf & ICE at local course
10.0 out of 10, Exceptional, (21)
"We absolutely enjoyed our stay. Great location, clean, and had everything we needed. Would stay there again. Excellent communication and customer service! Thank you!"
Newly updated water retreat. PONTOON for rent, FREE golf & ICE at local course
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!
9.8 out of 10, Exceptional, (134)
"Excellent property, excellent host, excellent weekend. Absolutely would come back."
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!
Fridge, microwave, oven, stovetop
Two bedroom suite with city views in the heart of downtown Madison
10.0 out of 10, Exceptional, (1)
The price is €550
per night
26 May - 27 May
Two bedroom suite with city views in the heart of downtown Madison
Fridge, microwave, oven, stovetop
Monona Home
10.0 out of 10, Exceptional, (19)
"Great property. Fenced in back yard great for dogs!"
Monona Home
Property grounds
Newly renovated home close to downtown New Glarus
10.0 out of 10, Exceptional, (48)
"Property is a perfect place for a getaway. House is blocks from downtown and neighborhood is absolutely charming. Great amenities and all the comforts of home. Hosts were great with communication and recommendations. Beds are super comfortable. We will absolutely love to stay there again."
Newly renovated home close to downtown New Glarus
Beach
Sweet beach front on Lake Koshkonong w/lots of room & a Paddleboat
9.4 out of 10, Exceptional, (36)
"This is a great house in a quiet neighborhood. The views of the lake were amazing! The pictures don't do it justice. We were very pleasantly surprised by how spacious the great room was and how much seating was available. Likewise the deck was a pleasant surprise with both comfy cushioned furniture as well as firmer chairs. Something for everyone and just a great place to hang out with lovely breezes from the lake. I contacted the host once for something I could not find and she responded...
Sweet beach front on Lake Koshkonong w/lots of room & a Paddleboat
Fridge, microwave, oven, stovetop
Cozy, Spacious Downtown Verona 3 Bedroom Home
10.0 out of 10, Exceptional, (17)
"The property was clean, tidy and highly functional. 5 stars!"
Cozy, Spacious Downtown Verona 3 Bedroom Home
Property grounds
Spacious Home + Fire Pit, Waterfall, Hot Tub, Home Theater! 20 min to DT Madison
10.0 out of 10, Exceptional, (13)
"We stayed the weekend to watch our son play baseball against University of Wisconsin. Go Illini!! We also celebrated his 21st birthday with 3 other families. The house was clean and had plenty of space for everyone to sleep comfortably. We would definitely rent this house again."
Spacious Home + Fire Pit, Waterfall, Hot Tub, Home Theater! 20 min to DT Madison
Exterior
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
10.0 out of 10, Exceptional, (18)
"Everything about our stay was fantastic! The house was nicely decorated and extremely clean. The kitchen was well appointed and had everything we needed. Beds were comfy. Shower was great. A perfect place for our group of friends to spend a long weekend. I wouldn’t hesitate to stay here again!"
The price is €494
per night
18 Jun - 19 Jun
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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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.

Other types of properties in Oregon you may be interested in

Exterior
Sleep Inn & Suites Oregon - Madison
2.5 star property
9.2 out of 10, Wonderful, (158)
"I got a room with two queen beds and the beds were way too soft and wasn’t comfortable. I wasn’t able to sleep on the beds as it gave me back pain. "
The price is €84
per night
23 Jun - 24 Jun
Sleep Inn & Suites Oregon - Madison
Exterior
The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, (1615)
"Everything was clean and neat. "
The price is €138
per night
26 May - 27 May
The Madison Concourse Hotel and Governor's Club
Exterior
Best Western Plus InnTowner Madison
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Friendly staff and very clean room. Seems recently remodeled."
The price is €144
per night
28 May - 29 May
Best Western Plus InnTowner Madison
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.

Everything you need to know about Oregon holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oregon holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oregon holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oregon holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oregon. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oregon holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oregon holiday rentals we have selected for you start as low as €123 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oregon rentals

At Expedia, we put the best Oregon holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oregon rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oregon holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oregon. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Legacy Guest House , Mount Horeb WI: This holiday home rental outside of Oregon offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable 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.

What can I see and do in Oregon?

Explore the area and family-friendly sights such as Henry Vilas Zoo, 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.

Recent reviews of Oregon properties
Expedia verified reviews