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Oregon Holiday Rentals

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Holiday Rentals in Oregon

Spacious 5-bedroom house sleeps 14 with pool, hot tub, sauna and more!

10.0 out of 10, Exceptional, (2)
"Perfect location for a family get together. Away from the hustle bustle, but close enough to restaurants and stores. House is clean, spacious and the pool is well maintained."
Spacious 5-bedroom house sleeps 14 with pool, hot tub, sauna and more!

The Dylin by Mint House

4.0 star property
9.2 out of 10, Wonderful, (97)
"Great stay at the Dylin"
The Dylin by Mint House

YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS

9.8 out of 10, Exceptional, (165)
"Had a phenomenal weekend celebrating my brothers engagement. House was plenty big enough to host 13 of us with a huge backyard and beds for everyone.Airconditioning worked very well too in what have otherwise been a very toasty few days. Would definitely stay here again"
YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS

Waterfront w/ Private Pier! Excellent Fishing Year Round! Sunsets & Swimming

9.4 out of 10, Exceptional, (108)
"The Island is a great place to stay. It’s right on the water, and we enjoyed long days relaxing, swimming and being out on the water on the stand-up paddle boards and in the kayaks. We had a wonderful night a night of fishing right off the dock when the lake was calm and our boys caught some fish. The sunsets were gorgeous. The kitchen is well stocked and beds are comfortable. The loft room is quite warm as the a/c or fans don’t cool it down so our boys slept together in the second bedroom to...
Waterfront w/ Private Pier! Excellent Fishing Year Round! Sunsets & Swimming

Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!

9.8 out of 10, Exceptional, (166)
"Great place!!"
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!

Pool with Slide. Great for Business Travelers!

The price is NZ$329
includes taxes & fees
5 Oct - 6 Oct
Pool with Slide. Great for Business Travelers!

Log Cabin at Lake Koshkonong - “The Overlook”

9.2 out of 10, Wonderful, (42)
"Nice quiet cabin. Quick response from host. Would stay there again. RTW"
The price is NZ$317
includes taxes & fees
28 Oct - 29 Oct
Log Cabin at Lake Koshkonong - “The Overlook”

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (64)
"A great place for a reunion of friends. Beautiful location with nearby trails. Host was excellent!!"
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Charming 2-bedroom cottage on Lake Koshkonong in Fort Atkinson, Wi.

10.0 out of 10, Exceptional, (4)
"The cottage was great. We enjoyed sitting the deck looking out on the water watching the boats. Very peaceful "
Charming 2-bedroom cottage on Lake Koshkonong in Fort Atkinson, Wi.

Charming 4-bedroom Lake house on Lake Ripley in Cambridge

9.6 out of 10, Exceptional, (16)
"Property was clean, kitchen was well-equipped, and plenty of room for all of us (7 adults, 2 toddlers). Beach was only a mile away and our private pier was great to hang out on. We had a great little weekend getaway and would definitely come back. "
Charming 4-bedroom Lake house on Lake Ripley in Cambridge

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (34)
"Had a great stay!"
The price is NZ$964
includes taxes & fees
5 Oct - 6 Oct
Doty ★ Walk to Everything -Hotel Quality- Downtown

Private Pool - HOT TUB - Sauna - Game Room - Pets

10.0 out of 10, Exceptional, (4)
"The house is great and the facilities in the house were well-functioning, and the dish washer saved us much time. The neighborhood is quiet and great views. We enjoyed our stay."
The price is NZ$1,804
includes taxes & fees
5 Oct - 6 Oct
Private Pool - HOT TUB - Sauna - Game Room - Pets

Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL

10.0 out of 10, Exceptional, (33)
"What a wonderful place to get the family together. Lots of space for relaxing and taking in the beautiful lake view. Many amenities to make your stay comfortable. "
Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL

Lakefront Access Cottage on Lake Koshkonong

10.0 out of 10, Exceptional, (13)
"No complaints about the spot! We were a little disappointed in the lake (definitely not swimmable) but that’s mostly on us for not doing our homework."
Lakefront Access Cottage on Lake Koshkonong

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (142)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

*Family Retreat* *Indoor Pool* *Arcade*

9.8 out of 10, Exceptional, (9)
"Great place. Love the big heated pool with a deep end. Arcade and table games was a nice touch. Very spacious and clean. "
*Family Retreat* *Indoor Pool* *Arcade*

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (43)
"Such a nice house! Great location and excellent amenities!"
The price is NZ$896
includes taxes & fees
7 Oct - 8 Oct
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Waterfront - Hot Tub - Sauna - Game Room - Pets

8.8 out of 10, Excellent, (5)
"This rental made for the perfect group weekend getaway. From the great shuffleboard table to the vintage arcade games like NBA Jam, this place was on fire! The beautiful view of the wide river from the hot tub was so tranquil a member of our group asked what lake we were on. It’s the perfect distance from Madison and Chicago that you feel like you’ve truly gotten away, but close enough that lots of activities feel easily accessible. The house was clean and well stocked with everything needed to...
The price is NZ$1,212
includes taxes & fees
6 Oct - 7 Oct
Waterfront - Hot Tub - Sauna - Game Room - Pets

Private Beach Waterfront w/ Dock - Rock River Hideaway

9.8 out of 10, Exceptional, (15)
"Nice spot for littles to enjoy the sand and adults to relax."
Private Beach Waterfront w/ Dock - Rock River Hideaway

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (128)
"We had a group of 5 and this worked out great. Beds were decently comfy. Utilized the fire pit which was a bonus."
Conveniently Located just off University Avenue on Madison's West Side
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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Top Oregon Hotel Reviews

Find out more about Oregon

Find out more about Oregon

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, 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 NZ$317 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?

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 an outdoor pool, a fireplace 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 balcony, a private garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Oregon?

Choose from 3 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 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 Wisconsin Brewing Company.

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.