Vacation rentals in Oregon

4.98 out of 5 average rating, 419 reviews

An inviting open space features a large custom breakfast bar with barstools, complemented by rustic stone walls and wooden beams. Chesterfield sofas provide comfortable seating, while natural light filters through the windows, creating a warm atmosphere. Decorative elements include vintage clocks and unique wall art.

Loft in Belleville

Mill House Retreat

The Mill House Retreat is a 2 story loft set in a park like setting next to the Sugar River. Built in 1864, this stone grist mill has soaring 15ft ceilings, original fittings and luxurious finishes. You will be greeted by chesterfield sofas, a large bar, a copper tub and comfortable beds. Just minutes to bike trails, live music, restaurants, and bars. Guests are welcome to have local friends over to enjoy the setting and reminisce. Madison, New Glarus and Epic are just minutes away.

Guest suite in Sun Prairie

A scenic view of a sunset reflecting vibrant colors in the sky over a tranquil waterway. Silhouetted trees create a natural frame along the shoreline, while gentle ripples on the water's surface capture the fading light of the day.

4.88 out of 5 average rating, 335 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

4.9 out of 5 average rating, 106 reviews

The kitchen showcases a dark countertop with white cabinetry above. A coffee maker stands beside a set of matching mugs, while an organized drawer reveals a variety of coffee pods and sugar options for guests' convenience. Natural light filters in through a nearby window.

Home in Fitchburg

Comfortable Madison Area Retreat In The Trees

Fully updated 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!

Guesthouse in Mount Horeb

The cozy studio retreat is nestled at the edge of a snowy yard, framed by tall trees. Sunlight filters through the branches, casting a soft glow on the rustic wooden exterior and a small set of stairs leading to the entrance.

4.96 out of 5 average rating, 603 reviews

Cool, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful one-room loft-style space featuring tall ceilings, an entire wall of sliding glass doors, kitchenette, piano, and an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs, included in your reservation, must be leashed when outside.

4.97 out of 5 average rating, 186 reviews

A spacious loft area features vaulted ceilings with exposed beams, allowing natural light from multiple skylights. The layout includes a designated sleeping area with a queen bed, a comfortable seating arrangement surrounding a smart TV, and a cozy nook with a pop of color from a yellow accessory.

Home in Madison

Lakeview Loft - Downtown Madison

Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).

4.98 out of 5 average rating, 191 reviews

A compact kitchen area is featured, showcasing a sleek silver refrigerator and a microwave. A coffee maker is positioned nearby on a wooden counter. A whiteboard with a welcoming message is mounted on the wall, alongside a holder with various brochures and a framed decorative sign.

Guest suite in Middleton

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

4.98 out of 5 average rating, 751 reviews

Two goats are seen in a wooden crate filled with straw, one lounging comfortably while the other stands nearby. The goats are a mix of brown and white, showcasing their distinctive ears and features.

Tiny home in Darlington

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

5 out of 5 average rating, 135 reviews

Apartment in Stoughton

Bees on Main: a Honey of a Place

Located in the heart of Stoughton's Downtown Historic District, "Bees on Main" is a lovingly renovated upstairs apartment. You'll find the Opera House, Chorus, and Stoughton's wonderful shops, restaurants, pubs, and galleries only steps away. The Yahara River and Fairgrounds are within a few blocks, and there's space on the private deck to safely store your bikes or kayaks if you want to enjoy the great outdoor activities and nature surrounding Stoughton.

4.94 out of 5 average rating, 372 reviews

A tranquil outdoor seating area features two green chairs positioned around a small fire pit. Surrounding trees and foliage provide a natural backdrop, while the ground is paved with gray stones, contributing to a cozy gathering space suitable for relaxation.

Guesthouse in Stoughton

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.

4.96 out of 5 average rating, 146 reviews

The welcoming entryway of the upper flat features a covered porch adorned with hanging lights and colorful potted plants. The charming exterior includes a mix of dark siding and stone accents, complemented by an inviting front path leading to the main door.

Apartment in New Glarus

Cozy Upper Flat in New Glarus

Welcome to my upper flat (private staircase to 2nd story) one block from Downtown New Glarus where you will find charming shops, tasty eats & activities! This unit can accommodate 4 people. There is a king sized bed & queen pull-out couch. Kitchen is fully stocked with a refrigerator, range/oven, toaster & coffee maker. Complete with cozy eat-in area! Living room has wall of windows & smart TV. W/D are included.

4.99 out of 5 average rating, 187 reviews

A modern bathroom is displayed with a light grey vanity and a white sink. Decorative frames hang on the dark green walls. A white toilet is positioned beside the vanity, while a small shelf holds toiletries. Soft lighting enhances the warm wooden floor.

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.

4.96 out of 5 average rating, 127 reviews

A coffee shop interior features a menu board listing coffee and tea options, positioned above a wooden counter. A small plant sits on the counter near a sink, and a trash can is visible beside it. Natural light filters through sheer curtains covering a window.

Apartment in McFarland

#302 Private Apartment in Historic McFarland House

This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1856 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Oregon vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Oregon

A serene outdoor area is presented, featuring a well-maintained lawn with various green plants and trees. A small blue shed is visible, along with colorful flags strung above. The space is complemented by flowerbeds that add gentle bursts of color to the lush surroundings.

4.92 out of 5 average rating, 283 reviews

1 sunny Yellow BR and lounge in Artist’s home!

WilliamRating, 5 stars1 week ago

I had a great stay! The house was clean and the hosts were very welcoming. The lounge space and coffee + tea were great touches. There were a lot of great paths and parks nearby and the hosts even had bikes to borrow. Couldn’t recommend enough!

A cozy outdoor seating area features a firepit surrounded by decorative stones. A foot in black sandals rests comfortably on the edge, while a nearby chair stands ready for use. Lush greenery, including a large tree and landscaped shrubs, creates a serene backdrop.

4.97 out of 5 average rating, 490 reviews

Spacious private level with garden view and more.

BeverlyRating, 5 stars4 days ago

Outstanding Airbnb. The room was spacious, fridge was stocked with bottled water and soda. Nice little kitchenette area. Cozy wonderful sitting area near the fire place looking out at gorgeous serene gardens. We spent hours on the patio! Bed was super comfy and quality linens were appreciated. Clean bathroom with toiletries and thick large towels. Loved all the art work, stained glass and collection of books. Guest book with recommendations was very thorough. Looking forward to returning next summer! Greg and Fred were great hosts!!

A spacious kitchen features modern cabinetry and a central island with seating. Natural light fills the room through windows, with a view of greenery outside. A dining table is set with blue placemats, while appliances and kitchenware are neatly arranged on countertops.

4.97 out of 5 average rating, 330 reviews

Mornings with Meg in Madison ZTRHP1-2020-00006

JasmineRating, 5 stars2 days ago

Meg was a very knowledgeable hostess - gave us detial information on places to go and things to do with young kids, shared great details of the history of the area. She was wonderful with kids. She let us use the kitchen to cook meals - which was very helpful to us. She was very kind to do some of our laundry. We would definitely stay here again!

The sitting room features hardwood floors and a large window allowing natural light. A vintage Pepsi vending machine is positioned against the wall, alongside a small TV on a desk. Comfortable seating includes a chaise lounge and a love seat, complemented by a decorative area rug.

4.97 out of 5 average rating, 810 reviews

Private Garden Level Guest Suite

BarbaraRating, 5 stars5 days ago

I enjoyed staying at Angie’s place! Cute, confortable with everything you could ever think you needed. Enjoyed chatting to Angie who was welcoming and friendly. A shame I was only there overnight. Thanks for a comfortable stay.

4.98 out of 5 average rating, 313 reviews

private, sunny lower level

LisaRating, 5 stars2 days ago

Jason is a welcoming and gracious host. He made us feel very much at home and was always responsive. The basement apartment worked great! Jason clearly put a lot of thought into designing a cozy place. There’s plenty of space and plenty of natural light. We also appreciated both having a kitchenette and access to the main kitchen. The location made it easy to get to the places we came to Madison to see, and it was also close to plenty of restaurants and other amenities. We would definitely stay here again!

A spacious wooden deck is adorned with various potted plants, including ferns and flowering plants in vibrant colors. Sunlight filters through the trees in the background, casting soft shadows on the deck, which is surrounded by a green lawn.

4.96 out of 5 average rating, 249 reviews

Private Ensuite with Queen Size Bed

NataliaRating, 5 stars6 days ago

Tara and Mike were great and even let me check in late due to travel delays. The space was very clean and the backyard deck was glorious! Great location, very cute cats and friendly hosts.

4.95 out of 5 average rating, 283 reviews

A modern kitchen is equipped with white cabinetry, a silver microwave, and a stove. A red kettle sits atop the stove, and a decorative piece rests on the counter. The backsplash features a mosaic design, while a framed image of outdoor furniture is displayed on the wall.

Private room in Verona

Private Bedroom downtown Verona.

NoahRating, 5 stars1 month ago

Such a wonderful apartment at such a great price! The decorations are absolutely gorgeous and the hosts are incredibly accommodating and kind.

A welcoming entrance features a pair of dark double doors. Accompanying the doors is a decorative wrought iron chair and a small shelving unit adorned with various items. A pathway lined with fallen leaves leads towards the entrance, framed by greenery on either side.