Holiday rentals in Eileen

Hayward Haus, Modern Design w/ Classic Experience

Built as a winter or summer escape for a couple or small group, this beautiful four season cabin is a great way to experience the Northwoods of Wisconsin in a modern, well-appointed, aesthetically rich space designed with relaxation in mind This cabin was built in 2021 and host is 13 year "superhost" This is a default "no pets" cabin, however exceptions can be made with permission and a fee. Inquire with host. NEMA 15-40R outlet provided for level 2 EV charging. You bring chord and adapter.

Ino Inn - Your Gateway to the Northwoods!

Experience the north woods in style! Only 1/4 mile, private trail, to the tri-county corridor. Direct access to 100's of miles of US Forestry roads, State and County groomed ATV & Snowmobile trails. Additional trails available on property. Only 30 miles to world famous Apostle Island National Lakeshore & Bayfield! Cabin is 1 hour east of Superior on US HWY 2 and 3 1/2 hours from Twin cities! Only 1/2 mile from INO Bar and Grill. (Please plan to bring your own towels, bedding is provided.)

One Minute Walk to Lake Superior. Brookside #11

Amazing location! This Comfy Studio Condo sleeps 4, Whirlpool tub/shower,King bed & Queen sofa sleeper. Strong Wifi, balcony, AC, CableTV and fire pit wood provided. 1 minute walk to the marina. Bayfield is 2.3 mi from Brookside. Hike or bike the Brownstone trail along the lake. Take the ferry to Madeline, cruise the apostles, Sail, fish, kayak, golf, orchards, ski and more!! The pool and restraunt opens July 1st. 5 minutes from Bayview beach, Mt Ashwabay, Big top and Adventure Brewery.

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

Bungalow (House) on Chequamegon Bay.

This newly renovated fully furnished home is located within one block from beautiful Chequamegon Bay, Ashland's Oredock Pier, walking and bike trail, boat ramp, and beach. Grab a pole and head down to fish off the Ashland Oredock pier, or pack up for picnic at the beach, launch your boat, kayak or canoe. Take a walk, bike, or run on the walking trails. It is short walk to a few local restaurants and the downtown area. Access snowmobile trails. No pets are allowed.

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

The Garland City Downtown Apartment

1920s, craftsman and art-deco-inspired apartment, furnished with antiques, located in the heart of Ashland’s Main Street Historic District. Ditch the car and walk to local amenities like the grocery store, brewpub, bars, restaurants, shops, library, and movie theater. View Ashland’s downtown murals. The Lake Superior waterfront is steps away...where you can stroll the shoreline path or bicycle the 9-mile town loop.

Cozy remodeled cottage in heart of Ashland

Cozy little cottage in quiet neighborhood in Ashland. Only five blocks from Chequamegon Bay. Completely remodeled in 2019. Home features two cozy bedrooms with queen sized beds. All new furniture and appliances. Nice deck with backyard to enjoy your morning coffee or evening meals. Downstairs area with large sectional sofa for kids, teenagers and Dad to get away by themselves!

Main street view apartment

The apartment is on the edge of the business district. A short walk to all the attractions. A quick two block to Lake Superior, or a block from the local brewery. Local bakery also only a few blocks away, as well as all of Ashland's local businesses. As you enter or exit the town, it is only one block off of US Highway 2.and makes finding your destination much easier.