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Oregon Holiday Rentals

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Holiday Rentals in Oregon

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
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
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (10)
"Space is clean, property is very pretty! Pool wasn’t ready for use, but can imagine it would add even more to the a summer stay! Owner is easy to communicate with. Ran into severe weather - owners were welcoming and ensured we were safe at all times. We will definitely be back to visit again!"
The price is NZ$211
includes taxes & fees
29 May - 30 May
Enjoy Nature with Full Comfort!
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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!
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
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
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
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
Exterior
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (187)
"We loved this house and the gardens! It is ideally located, a quick walk into town. The Frank Lloyd Wright accents compliment the furnishings and decor of the house to a tee. It is well-stocked with everything you need! Connie and Randy (the owners) are delightful. We will definitely stay here again when the opportunity arises."
A Pleasant Retreat- No Cleaning Fee & New Discounts
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!
9.8 out of 10, Exceptional, (134)
"We loved the deep lawn going down to the lake. We enjoyed cooking out and eating at the table on the lawn. Our dog loved playing stick and running. It was close to Ft. Atkinson, Edgerton and Stoughton. We would stay here again."
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!
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
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
Property grounds
Waterfront w/ HOT TUB + King Suite + Game Room
9.2 out of 10, Wonderful, (15)
"St pattys fun with friends and family"
The price is NZ$1,950
includes taxes & fees
5 Jun - 6 Jun
Waterfront w/ HOT TUB + King Suite + Game Room
Property grounds
Cozy cottage retreat that’s perfect for recharging.
10.0 out of 10, Exceptional, (37)
"This is such a great property! It is secluded but there are neighbors around; groceries and fast food places are close by. The home had so many places to gather, and it was so clean. We had a wonderful time!"
Cozy cottage retreat that’s perfect for recharging.
Beach
Sweet beach front on Lake Koshkonong w/lots of room & a Paddleboat
9.4 out of 10, Exceptional, (37)
"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
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
Marina
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
10.0 out of 10, Exceptional, (13)
"We loved our visit to Madison, made even more special with our stay in this awesome retro house! All of the special touches throughout the house were amazing, we would definitely stay here again in the future."
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Exterior
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
10.0 out of 10, Exceptional, (4)
"Our family enjoyed a delightful weekend stay at the EarthHouse for the graduation of our oldest son from UW. Pam wished us well from the onset & was extremely helpful when we added our middle son to our stay. At the time of booking, we were unaware that he would be able to join us for the graduation festivities. However, Pam accommodated our changing needs after arrival without creating any anxiety for us on our exciting weekend. We enjoyed a fantastic dinner in Mt Horeb Friday evening at Bistro...
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
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 NZ$879
includes taxes & fees
18 Jun - 19 Jun
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
TV
2 Bedroom - Main Street Sun Prairie WI
9.6 out of 10, Exceptional, (17)
"Overall awesome place. Chris stayed in contact the entire time but wasn’t overbearing. We enjoyed our stay."
The price is NZ$363
includes taxes & fees
11 Jun - 12 Jun
2 Bedroom - Main Street Sun Prairie WI
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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, (159)
"I didn’t like that Expedia was charged $163 n Expedia charged me $217, I will not book hotels with Expedia again!!"
The price is NZ$156
includes taxes & fees
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, (1644)
"We loved the Governor's lounge, it was nice to sit with a view of the capital building! Staff and service was excellent as well."
The price is NZ$411
includes taxes & fees
31 May - 1 Jun
The Madison Concourse Hotel and Governor's Club
Exterior
Best Western Plus InnTowner Madison
3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great breakfast and nice room. "
The price is NZ$287
includes taxes & fees
1 Jun - 2 Jun
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.

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?

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