Vacation rentals in Arena

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Top-rated vacation rentals in Arena

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Guest favorite

Cabin in Hill Point

4.97 out of 5 average rating, 500 reviews

Big R's Retreat Secluded and located in Nature

Welcome to our home: where we have found peace and relaxation for over 20 years. A German native, Big R fell in love with the open land and rolling hills of Wisconsin, becoming a US citizen in the 80s. He met Curly, a Chicago city girl, who brought a little city to his country life. They enjoy raising buffalo and spending warmer days on their porch enjoying the fresh air and beautiful views (with no mosquitos!). Now they want to share their idyllic and peaceful home with you. Drive down a dead-end road and pull up to a rustic cabin filled with high-tech and cozy amenities. We have something for everyone with a gas fireplace, tv (complete with dish, Cinemax, HBO and a Bluetooth sound system), board games and a full kitchen. Take a drink outside to soak in the hot tub or sit around the campfire. When the day is done, you will fall asleep instantly on the memory foam bed, either in the loft or the bedroom, and wake up to a beautiful sunrise looking out over your little getaway.

Guest favorite

Guest suite in Spring Green

4.9 out of 5 average rating, 141 reviews

Spring Green River Pines

Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

Guest favorite

Guest suite in Spring Green

4.79 out of 5 average rating, 147 reviews

River Valley Retreat

Enjoy your stay in the Spring Green Area! This private apartment in the lower level of our home is located on the edge of town - close to everything you're here to see! This space provides a home-like feel while you tour the area. Offering a one bedroom (queen bed) with the ability to sleep up to 4 more people (2 on sectional sofa and 2 on air mattress), plus a loaded kitchenette (no stove), dining area, bathroom, extra space for gaming (includes a free arcade and foosball) and private patio.

Guest favorite

Farm stay in Plain

4.94 out of 5 average rating, 204 reviews

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

Fully-renovated 1890s cabin located on a 60+ acre farm just north of Spring Green. The cabin has radiant floor heat, is air conditioned, has a small kitchenette, bathroom with shower, and wireless internet. The farm has a barn from 1895, a main home built in 1923, apple trees, hiking trails, creek with a swimming hole, and a large hill with marvelous views. Make this your private weekend cabin or a longer-term retreat. Farm powered primarily by a large solar array atop one of the barns.

Guest favorite

Bungalow in Richland Center

5 out of 5 average rating, 275 reviews

GloryView Ridgetop Bungalow

Farmhouse Bungalow sits on top of a ridge in the Southwest WI driftless area, boasting spectacular views. A site that works for anyone from a relaxing retreat to a great spot for adventures. Fall photography dream, cyclists paradise, star gazing/campfire, hiking, kayaking, canoeing, fly fishing, Frank Lloyd Wright, WI Dells and other local attractions. The home was completely renovated with all the modern conveniences but the Farmhouse charm. A sleeping loft adds additional functionality.

Guest favorite

Guesthouse in Mount Horeb

4.96 out of 5 average rating, 584 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.

Guest favorite

Home in Arena

4.94 out of 5 average rating, 141 reviews

Sugarland Farmhouse

Sugarland Farmhouse is a fully restored 1850’s colonial revival farmhouse tastefully decorated with primitive antiques. The two-story house has hardwood plank floors that are accented with both antique and updated furniture and decor. Porches reveal views of the surrounding countryside. Situated in a major southern Wisconsin tourism area, we are 30 minutes from Madison and 10 minutes from Spring Green home of Frank Lloyd Wright’s Taliesin, American Player’s Theater, and House on the Rock.

Guest favorite

Guesthouse in Mineral Point

4.94 out of 5 average rating, 238 reviews

Lumber Yard Cottage, a cozy retreat

The Lumber Yard Cottage is a cozy hidden retreat tucked away from the road. Within walking distance of all Mineral Point has to offer. Great restaurants on all sides of this property and wonderful shops are just up the road. The Cheese Trail and railroad museum are across the street. Enjoy the back porch with the wraparound stone wall or the lovely front porch and watch the world slowly drift by. There is a queen size bed, jacuzzi tub, gas fireplace, ac unit, full kitchenette, and wi-fi.

Guest favorite

Guest suite in Middleton

5 out of 5 average rating, 163 reviews

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.

Guest favorite

Guest suite in Spring Green

4.96 out of 5 average rating, 135 reviews

Casa Natura

Located on a private 60 acres woodland and rock outcroppings. Walking paths, bluff climbing, wild edible foraging! A haven for birds and wildlife! Near the artist community of Spring Green, American Players Theater, and home to Taliesin and House on the Rock. The Wisconsin river is accessible (9 miles) for fishing,canoeing, kayaking and swimming. Great Hiking and waterfall at nearby Governor Dodge State Park. 40 miles from Madison,WI capital. We speak English, Spanish and Italian!

Guest favorite

Tiny home in Darlington

4.98 out of 5 average rating, 675 reviews

Arbor Crest Cottage- Peaceful farm stay getaway.

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.

Guest favorite

Farm stay in Mount Horeb

4.97 out of 5 average rating, 113 reviews

Campo di Bella Winery & Family Farm LLC

Welcome to Campo di Bella Farmstay. We have created a private retreat above our winery on our farm. You will enjoy the sights and sounds of country living. Weekend Farm to Table dinners available on-site and we typically reserve seating for our farmstay guests. From Dec. 8th, 2023- March 31, 2024, we are only offering dinners on Friday nights. Max room rate $175.00. Please note that during winter months, we are on a private road and snowplowing may be completed by early afternoon.