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Oregon Vacation Rentals

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Dec 2 - Dec 3
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Vacation Rentals in Oregon

Private kitchen
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

Cottage in Milton

2.0 star property
9.6 out of 10, Exceptional, (5)
"This property was perfect. We were a group of women togther for a birthday and the house was just right. It had everything we needed in the kitchen to prepare meals. Plenty of towels.The beds were all comfortable.Such a beautiful, quiet location. It is only a walk away from the lakeComunnication with the owner was no problem."
United States
Michelle C.
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
Interior
Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Condo in Edgerton

2.0 star property
10.0 out of 10, Exceptional, (5)
"The feel was exactly what we were looking for! Great and very helpful staff!! Highly recommend and will more than likely stay again!!"
United States
Jeff M.
The price is ￥15,618
￥39,710 total
includes taxes & fees
Dec 3 - Dec 4
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
Interior entrance
The Dylin by Mint House

Aparthotel in Tenney-Lapham

4.0 star property
9.4 out of 10, Exceptional, (117)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The price is ￥16,210
￥18,723 total
includes taxes & fees
Dec 23 - Dec 24
The Dylin by Mint House
Property grounds
Log Cabin at Lake Koshkonong - “The Overlook”

Cabin in Edgerton

9.2 out of 10, Wonderful, (47)
"Checkin was super easy, great amenities, and cozy cabin atmosphere."
United States
Nicholas R.
The price is ￥10,734
￥25,274 total
includes taxes & fees
Dec 4 - Dec 5
Log Cabin at Lake Koshkonong - “The Overlook”
Property grounds
Your Holidays Start Here HotTub/Arcade/Fireplace

Vacation Home in Milton

10.0 out of 10, Exceptional, (17)
"Excellent place!"
United States
Roger Z.
The price is ￥17,542
￥84,793 total
includes taxes & fees
Dec 8 - Dec 9
Your Holidays Start Here HotTub/Arcade/Fireplace
Fridge, microwave, oven, stovetop
Cannery Square Unit - 106 by Patriot Properties

Apartment in Sun Prairie

9.4 out of 10, Exceptional, (26)
"Great place "
United States
Armando
The price is ￥19,756
￥49,703 total
includes taxes & fees
Dec 9 - Dec 10
Cannery Square Unit - 106 by Patriot Properties
Exterior
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

Vacation Home in Mount Horeb

10.0 out of 10, Exceptional, (18)
"We had a nice time here. Easy to get in and out. Very accommodating and clean! Pretty cool place to stay in! "
United States
Kyle H.
The price is ￥16,087
￥29,167 total
includes taxes & fees
Dec 6 - Dec 7
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Lobby
Pool with Slide. Great for Business Travelers!

Apartment in Fitchburg

The price is ￥15,278
￥20,765 total
includes taxes & fees
Dec 11 - Dec 12
Pool with Slide. Great for Business Travelers!
Exterior detail
Cannery Square Short Term Rentals -104 by Patriot

Apartment in Sun Prairie

9.8 out of 10, Exceptional, (42)
"Walkable restaurants. "
United States
Mike H.
The price is ￥19,756
￥49,703 total
includes taxes & fees
Dec 3 - Dec 4
Cannery Square Short Term Rentals -104 by Patriot
TV, offices
2 Bedroom - Main Street Sun Prairie WI

Apartment in Sun Prairie

9.6 out of 10, Exceptional, (34)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
The price is ￥18,978
￥48,827 total
includes taxes & fees
Dec 16 - Dec 17
2 Bedroom - Main Street Sun Prairie WI
Fridge, microwave, oven, stovetop
New Luxury & Spacious House in the Heart of Janesville

Vacation Home in Janesville

2.0 star property
9.0 out of 10, Wonderful, (4)
"Great to have your own place in a nice area of town. "
United States
Amanda E.
The price is ￥27,581
￥74,210 total
includes taxes & fees
Dec 3 - Dec 4
New Luxury & Spacious House in the Heart of Janesville
Outdoor dining
Enjoy Nature with Full Comfort!

Apartment in Verona

9.2 out of 10, Wonderful, (37)
"Well-appointed, very clean space on a stunning property! Easy check-in. Everything we needed. Good communication with the host. We hope to return!"
United States
Thea S.
The price is ￥12,600
￥19,858 total
includes taxes & fees
Dec 10 - Dec 11
Enjoy Nature with Full Comfort!
Outdoor dining
Sugar River Suite - Your Sweet Escape in the Heart of it All!

Apartment in New Glarus

10.0 out of 10, Exceptional, (20)
"Super clean & right in the middle of town. Great place for a girls getaway weekend!"
United States
Rachel I.
The price is ￥17,570
￥28,045 total
includes taxes & fees
Dec 3 - Dec 4
Sugar River Suite - Your Sweet Escape in the Heart of it All!
Lobby
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Condo in Fitchburg

The price is ￥18,039
￥23,883 total
includes taxes & fees
Dec 4 - Dec 5
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fridge, microwave, oven, stovetop
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Vacation Home in Village of Cottage Grove

10.0 out of 10, Exceptional, (7)
"Very nice duplex with everything you could need. Super quiet neighborhood. Would stay here again if in the area."
United States
Matt W.
The price is ￥23,334
￥71,684 total
includes taxes & fees
Dec 7 - Dec 8
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Fridge, microwave, oven, stovetop
Hot Tub - King Suite - Game Room - Large Groups

Vacation Home in Sun Prairie

10.0 out of 10, Exceptional, (15)
"We had a great visit "
United States
Jennifer D.
The price is ￥26,601
￥89,018 total
includes taxes & fees
Dec 3 - Dec 4
Hot Tub - King Suite - Game Room - Large Groups
Fridge, microwave, oven, stovetop
Boomerang Home Rentals #13-RA

Vacation Home in Janesville

2.0 star property
The price is ￥25,667
￥83,691 total
includes taxes & fees
Dec 27 - Dec 28
Boomerang Home Rentals #13-RA
Fridge, microwave, oven, stovetop
Doty ★ Walk to Everything -Hotel Quality- Downtown

Vacation Home in Downtown Madison

9.8 out of 10, Exceptional, (36)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is ￥26,461
￥45,296 total
includes taxes & fees
Dec 7 - Dec 8
Doty ★ Walk to Everything -Hotel Quality- Downtown
Property grounds
A Pleasant Retreat- No Cleaning Fee & New Discounts

Vacation Home in Sun Prairie

10.0 out of 10, Exceptional, (259)
"A great stay! A wonderful location and excellent property, along with kind and warm hosts. Thank you. "
United States
Rachel Z.
The price is ￥42,950
￥54,996 total
includes taxes & fees
Jan 1 - Jan 2, 2026
A Pleasant Retreat- No Cleaning Fee & New Discounts
Exterior
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Vacation Home in Monona

9.8 out of 10, Exceptional, (47)
"Such a nice house! Great location and excellent amenities!"
United States
Carson M.
The price is ￥37,129
￥77,452 total
includes taxes & fees
Dec 7 - Dec 8
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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

Hampton Inn & Suites Madison / Downtown

Hampton Inn & Suites Madison / Downtown

10/10 Excellent
"Yes"
Earl 1-night trip
Posted 2 days ago
Hampton Inn & Suites Madison / Downtown

Find out more about Oregon

Search for holiday rentals in Oregon on Expedia! You can easily find your home rentals, villas, holiday apartments in Oregon using one of the methods below:

  • View our selection of featured holiday rentals in Oregon
  • Use the map to find apartments and other holiday homes in the Oregon neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oregon while they last

Look no further and take a look at our great range of rental properties in Oregon!

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?

220’ WATERFRONT BEACH ROCK RIVER WI PETS PIER POOL FP KYAKS FISHNG BOAT INCLUDED: This vacation home rental near Oregon is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Oregon?

Choose from 3 Expedia vacation rentals in Oregon for a memorable vacation.

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 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.