Holiday rentals in Oregon

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.

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

Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna

Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces. Two parking spots included. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.

Spacious Basement Apartment near Epic and Madison

We first used AirBnB when we traveled to Paris and Barcelona in 2015. We were happy with our stay but thought there was room for improvements. When we purchased our home in Verona we saw the potential for using part of it for AirBnB. From our experiences, we designed and decorated our space with a simple focus – what would we want in a nightly rental. The result was a spacious, clutter-free, and cheerful place where guests could feel comfortable while away from their own homes.

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!

Le Gallus Palace - 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.

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!

Madison's First EcoLodge

Welcome to Premier Ecolodge on Monroe Street! Award winning 3800 sq. ft. home, with 3 guest rooms with queen beds and whirlpool baths, and 2 large bedrooms with for 4 beds, for a total of 12 guests. Relax in the sauna and enjoy a full kitchen to share your favorite meals. The house is near great restaurants, biking, running trails, and the Arboretum. Lake Wingra trail is across the street. UW and State Street are a mile away. Previous superhosts under new management.

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!

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.

Downtown Verona Hideaway

PRIVATE HIDEAWAY CLOSE TO VERONA'S DOWNTOWN , SPACIOUS LIVING, WASHER/ DRYER & NOON CHECKOUT. 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.

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