
Holiday houses in Oregon
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Oregon
Guests agree: these stays are highly rated for location, cleanliness and more.

YurtSimple
YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Cottage Suite + Jacuzzi Bathtub & Sauna
This Suite is perfect for 1-5 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond/Bodywash

Waterfront modern cabin w/ kayaks
VERY romantic getaway for 2! Enjoy your own private dock, welcome to tie off your own boat or rent locally. Complimentary use of 2 kayaks. Beautiful modern riverfront cabin near Lake Koshkonong's eateries and entertainment. Soak in the gorgeous Wisconsin summer with water activities at your fingertips. The rest of the year take in the pristine wonderland views in our enclosed balcony. Only 30 minutes from Madison's world class culinary experiences, performance arts, sports & festivals.

Sauna | Hot Tub | EV+ | Luxury | Cozy | Private
Nestled in the country, this luxurious home offers a serene escape from the hustle of city life. Enjoy two spacious bedrooms and two meticulously designed bathrooms featuring indulgent amenities, such as a deep soaking tub. A cozy living area with a stone fireplace invites relaxation, while a gourmet kitchen beckons culinary adventures. Outside, soak in the hot tub, grill up some dinner, share stories around the fire, or watch the sunset from the sauna, all amidst nature's embrace.

Madison Lakefront Oasis in the Heart of Madison
Enjoy all that Madison has to offer from this beautiful lakefront property. BRING YOUR BOAT, our private dock on Yahara River has 3 slips with access to both Lake Monona & Lake Waubesa. Central location offers multiple restaurants, shops & public boat launch all within walking distance. Breath-taking sunsets over the lake. Quick 5-10 minute commute to downtown Madison, UW-Campus, Hospitals, Alliant Energy & Sylvee, State Street, hundreds of other Madison attractions east or west side!

Charming Milkhouse Cottage, minutes from Madison!
Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!

Comfortable Madison Area Retreat In The Trees
Tri-level duplex centrally located in Fitchburg. Nestled in a quiet residential neighborhood backing up to a small patch of woods for privacy. Feel away from it all with the sights and sounds of nature yet close to all the modern conveniences. Enjoy separated living spaces, a fully equipped kitchen (per WI health code, edable cooking supplies, are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!

Main St 2 Bdrm - Walk to coffee & sushi!
* Be sure to check out our winter extended stay discounts for 3+ nights! * Welcome to historic downtown Oregon! Nestled in a picturesque setting, this elegant retreat combines modern comfort with historic charm. You'll be steps away from locally owned coffee and gift shops, a wine reserve & restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!

Historic Home -Private Apartment
Oregon is a short drive to Madison, Wisconsin’s capital city. Oregon has a budding downtown business district 2 blocks away. Our lower level private apartment is great for couples, friends, families, and business or healthcare travelers. We created the apartment when we built a new addition onto our home in 2014. The apartment has a separate secure private exterior entrance and secure private interior entrance. There is a Ring camera that overlooks the parking area.

Far Westside Home Away From Home
Your own 820 square foot space with full bathroom. Located 6.2 miles from the UW Madison. Inside, you will find a bedroom with a queen bed, living room w/a comfortable queen size sofa bed, a 54”HDTV, a kitchenette (not a full kitchen) w/a dining room table, a mini-fridge, and a library. To see a video of the space go to YouTube and search on “v=hDgEasBTxoA” (cut and paste recommended). ZTRHP1-2020-00044

Contemporary home near Madison
Located in a quiet neighborhood only twenty minutes away from Madison, this contemporary home is the perfect place for large groups. The home has three spacious bedrooms with a large kitchen and two outdoor patios for entertaining. It is a great place to relax and enjoy the Wisconsin weather inside and out! If you require additional sleeping accommodations, an air mattress can be made available.

The Loft Retreat
A newly remodeled one bedroom apartment with the bedroom overlooking the Village Park. Contains a spacious bathroom with a walk in shower and a kitchenette with a refrigerator, microwave, Keurig coffee maker and a toaster. You can set out on the deck and enjoy your morning coffee or relax watching the large TV with 20+ channels plus internet television.
Popular amenities for Oregon holiday rentals
Other great holiday rentals in Oregon

13 Mi to University of Wisconsin: Suburban Home

Riverview Retreat

Lake Happy | Chic Stay Steps from Lake Beulah

Secluded Country Rustic Barndominum

Downtown Verona: Cozy Hideaway

10 miles from Madison, WI!

Par-fect Escape on Lake Windsor Golf Course

River front house at Machesney Park
Destinations to explore
- Chicago Holiday rentals
- Upper Peninsula Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Minneapolis Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Traverse City Holiday rentals
- Ann Arbor Holiday rentals
- Wisconsin Dells Holiday rentals
- Madison Holiday rentals
- Devil's Lake State Park
- Wisconsin State Capitol
- Lake Kegonsa State Park
- House on the Rock
- Wollersheim Winery & Distillery
- Mirror Lake State Park
- Cascade Mountain
- Governor Dodge State Park
- Henry Vilas Zoo
- Glacier Canyon Lodge
- Tyrol Basin
- American Players Theatre
- Camp Randall Stadium
- Chazen Museum of Art
- Overture Center For The Arts
- Rock Cut State Park
- Dane County Farmers' Market
- Madison Childrens Museum
- Monona Terrace Community And Convention Center
- Ho-Chunk Gaming Wisconsin Dells
- Nicholas Conservatory And Gardens
- Alpine Valley Music Theatre
- Cave Of The Mounds Lowest Point
- Parfrey's Glen State Natural Area





