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Oregon Vacation Rentals

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Vacation 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 CA $112
CA $176 total
includes taxes & fees
May 28 - May 29
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 CA $661
CA $1,464 total
includes taxes & fees
Jun 3 - Jun 4
Waterfront w/ HOT TUB + King Suite + Game Room
Property grounds
Cozy cottage retreat that’s perfect for recharging.
10.0 out of 10, Exceptional, (36)
"This property and cottage was even better than we expected! Jeff was always available and answered all questions promptly. The greenhouse and sunroom, (that overlooks the river) seemed to have healing powers! The entire cottage offered so many opportunities to recharge that you don't feel a need to 'go somewhere ' or 'do something '. Thank you, Jeff for sharing your wonderful home away from home with us."
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, (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
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
Interior
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
Living area
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 CA $358
CA $728 total
includes taxes & fees
May 28 - May 29
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 CA $143
CA $305 total
includes taxes & fees
May 28 - May 29
2 Bedroom - Main Street Sun Prairie WI
Don't see what you're looking for?
See all available properties in Oregon
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 Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Oregon private vacation homes
Known landmarks
Stoughton Opera House, Wisconsin Brewing Company and Troll Beach
International airport
Milwaukee, WI (MKE-General Mitchell Intl.)

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 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 CA $115
CA $130 total
includes taxes & fees
Jun 23 - Jun 24
Sleep Inn & Suites Oregon - Madison
Exterior
The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, (1635)
"Prompt room service"
The price is CA $245
CA $283 total
includes taxes & fees
May 28 - May 29
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)
"I like the location =, it is close university and university hospital"
The price is CA $205
CA $237 total
includes taxes & fees
May 29 - May 30
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Oregon?

Yes, you can find vacation rentals close to the most popular points of interest in Oregon, or you can select a more remote option if you're looking for a relaxing stay. Oregon is known for its golf courses.

What are some of the best vacation home rentals in Oregon?

Legacy Guest House , Mount Horeb WI: This vacation home near Oregon offers a patio, a barbecue grill, 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 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 larger area, you’ll find Legend at Bergamont and Alliant Energy Center.

What are vacation rentals like in Oregon?

Vacation rentals are private properties you can stay in for a short or long stay in Oregon. Vacation rentals feature amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.

Recent reviews of Oregon properties
Expedia verified reviews