Vacation rentals in Oregon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oregon

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A comfortable living area features a black leather sofa adorned with red and yellow pillows. A wooden coffee table sits in front, and a colorful area rug adds warmth to the space. The background reveals a well-lit kitchen with modern fixtures.

Home in Madison

Charming Campus Area Home • Entire Home Near UW

Steps to Camp Randall & an easy walk to UW–Madison! Spacious home for up to 10 guests with a comfortable layout, multiple bedrooms, full kitchen, and inviting gathering spaces. Enjoy the back patio—perfect for unwinding after a day on campus or exploring the city. Ideal for Badgers game weekends, family visits, and group stays. Please note: during football weekends, the host may use the garage and part of the driveway for tailgating; parking may be shared. Cleaning fee $150. No pets or smoking.

LocationValueAccess

4.98 out of 5 average rating, 285 reviews

Guest favorite

A serene outdoor seating area is highlighted by four wicker chairs arranged around a round table. Lush greenery surrounds the space, and views of the tranquil lake create a peaceful atmosphere. A subtle path leads toward the water's edge, with distant docks visible.

Home in Middleton

Luxury Lakeside Oasis- 4 Bed / 3 Bath Lake Home

Enjoy time with your loved ones at our luxury lake front oasis. Breathtaking views combined with the ideal Middleton location & extensive updating make our home the perfect vacation destination. Huge windows maximize gorgeous views of 60+ feet of lake frontage. A fully updated kitchen boasts custom everything. Our home features: 4 bedrooms, 3 bathrooms, lofted office, open kitchen with an island & dining table. A short drive (5-7 mi) to UW Campus, Camp Randall, Kohl Center & Wi State Capitol

LocationFamilyGrill

5.0 out of 5 average rating, 20 reviews

Top guest favorite

The exterior of a modern two-story home is showcased with a welcoming front yard and driveway. A cozy screened patio is visible with colorful outdoor seating. The game room features a foosball table and arcade cabinet, while a dedicated office area is equipped with a desk and dual monitors.

Home in Verona

Badger’s Retreat - Suburban Oasis w/Epic Amenities

Welcome to your home away from home, just 15 minutes from Madison and near Epic headquarters. The “Badger’s Retreat” includes a fully-equipped office with high-speed internet, perfect for both work and leisure. The kitchen is ready for your family meals, while the game room features a wet bar, wine fridge, and over 17,000 arcade games. Step outside to the cozy fire pit or dine al fresco on the screened patio. Enjoy making lasting memories in this comfortable, thoughtfully-appointed retreat!

LocationFamilyKitchen

4.98 out of 5 average rating, 95 reviews

Guest favorite

This spacious bedroom contains a comfortable bed dressed in white linens, with a decorative throw and pillows. Natural light filters through the window, illuminating a wooden dresser and bedside tables. A textured area rug adds warmth to the room, creating a cozy atmosphere.

Home in Fitchburg

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, edible cooking supplies are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!

LocationValueDecor

4.91 out of 5 average rating, 158 reviews

Top guest favorite

A small deck area is illuminated by soft outdoor lighting, featuring a table with two chairs. The structure is surrounded by greenery and a fence, with large glass doors providing views of the serene landscape beyond. A calm evening atmosphere is present.

Tiny home in Oregon

Le Gallus Palais - A Tiny House

Escape to Le Gallus Palais, a cozy tiny house on a peaceful farm just 20 minutes from Madison, WI. Surrounded by farm fields, and a chicken yard, with access to a spiral orchard with tame ducks and a koi pond, this private retreat offers charm, comfort, and serenity. Enjoy a restful stay with a comfy bed, kitchenette, and nature all around. Perfect for a romantic getaway, solo retreat, or creative escape. Get the best of both worlds - country vibe with modern amenities.

LocationDecorSleep quality

4.98 out of 5 average rating, 51 reviews

Guest favorite

A spacious living area features a modern design with comfortable leather sofas, a round coffee table, and a large television. The open layout leads to a dining area and a fully equipped kitchen, illuminated by natural light from the windows.

Home in Fitchburg

Luxurious & Spacious 4 BR Home w/o Cleaning Fees

Escape to our stunning Madison home! Luxuriate in the sleek contemporary design, spacious living areas with high-end finishes and tasteful furnishings. Unwind in the comfortable bedrooms with ample storage. Step outside to our backyard oasis for al fresco dining and relaxation. Our exceptional customer service and thoughtful touches guarantee an unforgettable stay. Close to Madison's best shopping, dining, and entertainment. Book now for an experience you won't forget!

FamilyLocationCleanliness

4.96 out of 5 average rating, 112 reviews

Top guest favorite

Apartment in Madison

The Wilson O | Bright 2BR with Custom Detail

Located within The Wilson, this beautifully crafted second-floor two-bedroom blends historic charm with modern comfort. Featuring local artwork, custom beds, and curated furnishings, the front-facing apartment is filled with natural light and city views. Guests enjoy access to a shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtful spaces. Second-floor walk-up with paid parking nearby.

LocationFamilyCheck-in

5.0 out of 5 average rating, 73 reviews

Top guest favorite

Apartment in Verona

Downtown Verona Hideaway 2

PRIVATE LARGE HIDEAWAY CLOSE TO VERONA'S DOWNTOWN , SPACIOUS LIVING, SECONDARY LIVING SPACE W/ WASHER/ DRYER. Walking distance to restaurants, bars, shopping, library, Farmer Market etc. on quiet street in bustling downtown Verona. Inviting and comfortable space for you to enjoy and relax during your vacation. This is fun duplex near a playground and walking/biking/ running trails. Walking distance to restaurants, bars, shopping, library, Farmer Market etc.

FamilyValueParks

4.98 out of 5 average rating, 47 reviews

Top guest favorite

A cozy living room features a plush orange sofa paired with two gray armchairs. A wooden coffee table is positioned in front, displaying magazines. The room is illuminated by natural light through three windows, and a flat-screen TV is mounted above a decorative fireplace.

Apartment in Oregon

Main St 1 Bdrm - Steps to the Wine Reserve!

Welcome to historic downtown Oregon! Step into the past while enjoying modern comfort in this beautiful space, which once housed our 1st library! Just steps away from locally owned coffee and gift shops, a wine reserve, and amazing 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!

ValueFamilyHospitality

4.97 out of 5 average rating, 133 reviews

Top guest favorite

An outdoor patio features a seating area with a couch and chairs, surrounded by greenery. A small table is seen beside a larger dining table, providing a space for gathering. Sunlight casts gentle shadows over the wooden deck, enhancing the inviting ambiance.

Home in Oregon

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.

FamilyLocationLaundry

4.99 out of 5 average rating, 234 reviews

Top guest favorite

Home in Madison

Historic guesthouse near UW

Featured on the National Register of Historic Places, this unique 1916 "granny cottage" stands behind our home in the gorgeous Village of Shorewood Hills. Centrally located, we are just a few walkable blocks from UW Hospital and Picnic Point, and walking/biking distance from UW, the Capitol, Hilldale Shopping Mall, Whole Foods, and plenty of restaurants.

FamilyLocationCheckout

4.95 out of 5 average rating, 66 reviews

Guest favorite

A private front porch features comfortable seating options, surrounded by lush greenery and manicured lawns. The view includes soft sunlight filtering through trees, providing a serene outdoor space perfect for relaxation. A white railing enhances the openness of the porch, creating a welcoming atmosphere.

Apartment in Madison

Charming 3 Bedroom near Capitol and Alliant Center

A welcoming getaway within walking distance of the Capital Square and the Alliant Energy Center/Colliseum. Enjoy the quiet privacy of the entire 2nd floor unit. Located in a vibrant and centrally located neighborhood with coffee shops, restaurants, and bars nearby. Madison Permit: #ZTRHP1-2021-00011

LocationFamilyLaundry

4.93 out of 5 average rating, 357 reviews