
Vacation rentals in Orangeville
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Orangeville
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

Relaxing 3 Bedroom Cabin with Hot Tub and Scenery
Tucked away in the rolling hills of Southern Wisconsin sits a little log home ready for your arrival. Hand built by the caretaker and his family; the Braezel Branch Retreat is named after the stream that runs through the valley. Relax with the whole family in this two-bedroom, two-bathroom cabin with a comfortable open floor plan. Wander through the beautiful walking trails and enjoy the view of the valley from the large front porch. There is also local tubing, kayaking, golfing and wineries.

Historic Randall Schoolhouse
You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Rustic Barn Loft at Oak Springs Farm
Unplug in our gorgeous barn loft above our working barn. Sleep to the sound of crickets and frogs in the pond, then wake up and pet the sheep, goats, rabbits, cats, ducks & chickens. Open floor plan, cathedral ceiling, farm decor, fire pole, sliding barn doors. Full kitchen, jetted tub, rain shower, laundry. Stone patio, fire pit. 2 bedrooms, sleeper sofa, air mattresses. Juice, coffee, and fresh eggs provided when the hens are laying. NO A/C. ABSOLUTELY NO PETS Facebook oakspringsfarmwi

Adults Only "Red Room" Home with Hot Tub
Unique adult themed home with a BDSM / "Red Room" experience. It's a great way for couples to turn their fantasies into reality and explore with each other. Includes St Andrews Cross, Swing, and Sybian! Relax on the patio or in the hot tub with a scenic view of the Rock River. Once you arrive you will not want to leave so we try to provide you with everything you may need for your stay! Frozen pizzas, Bottled Water, Coffee, Robes, Firewood and a special gift with each reservation.

Lower Level Suite in Home-Private Entrance!
⭐️ Large lower level walk out apartment for up to 7 people, ⭐️separate entrance in single family home in a quiet upscale neighborhood. 💡Lighted sidewalk. ⭐️Gas in wall heater supplements heating needs in winter. Sleeps up to 7 guest with 🛌1 king bed (heated mattress pad) in master, common area has 🛌 4 Twin XL beds w/memory foam mattresses and 🛌 1 additional Twin XL bed in bonus room. ⭐️ Free Washer/Dryer in apt. w/3 courtesy soap pods. 👶🏻 Pack n Play 🍼 high chair.

Galena Country Getaway
Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

Hamilton Goebel House
This house is a historic home that was built in 1833 on land owned by Jamison Hamilton, the founder of Darlington. It is not known if he actually lived in the house,but could be assumed. During your stay you will find bits of history and pictures that have been gathered along the way.It has all the comforts of home. A beautiful four bedroom home that has been completely renovated to reflect the old and new times. This home was on the list to be torn down by the city.

Cozy Cabin on Decatur Lake
Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

The Dairy at the Wegmueller Farm
Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.

Cute Little Country Guest House
An old barn/machine shed transformed into a great little rustic retreat (which we affectionately call "Westhaven")! A great secluded place to get away from the day-to-day grind. Hiking trails on the premises. About 5 miles from civilization (town). Come unwind! FRIENDLY DOGS WELCOME (we speak fluent WOOF! :-) ) (Please NO cats!) This is not just a place to stay, but an experience to remember.

Welcome to the "Bat Cave"!
Completely renovated 3 bedroom, 2 bathroom home with walk in basement allowing easy access for ATV and snowmobile enthusiasts. Direct access to the Cheese Country trail and one block from The Vault and Cash's bar and grill! Amenities include washer and dryer, wifi, 3 smart TV's and a unique gathering spot with poker table in the basement.
Popular amenities for Orangeville vacation rentals
Other great vacation rentals in Orangeville

The Main St Place 2nd floor Mount Carroll IL

Secluded Log Cabin w/ Private Lake & Hiking Trails

Whispering Woods Estate-relax, recharge, connect

The Orchard House

Walk everywhere in downtown Freeport.

The Farmhouse country ranch

Luxury Condo | King Bed | 2BR 2BA | Great Location

Updated Unit w/Panoramic Views
Destinations to explore
- Chicago Vacation rentals
- Platteville Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- St. Louis Vacation rentals
- Minneapolis Vacation rentals
- Milwaukee Vacation rentals
- Wisconsin River Vacation rentals
- Traverse City Vacation rentals
- Madison Vacation rentals
- Wisconsin Dells Vacation rentals
- Twin Cities Vacation rentals
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Governor Dodge State Park
- Henry Vilas Zoo
- US Grant Home State Historic Site
- Camp Randall Stadium
- Rock Cut State Park
- Chazen Museum of Art
- Overture Center For The Arts
- Dane County Farmers' Market
- Madison Childrens Museum
- Monona Terrace Community And Convention Center
- Galena Cellars Vineyard
- Nicholas Conservatory And Gardens
- Cave Of The Mounds Lowest Point
- Discovery Center Museum
- Tyrol Basin
- Blue Mound State Park





