Holiday rentals in Eileen

Entire- Cozy Chequamegon Home

Escape suburbia at our quaint farm style house about a mile from Lake Superior and about 1/2 mile from Northland College. Guests describe our home as cozy & reminiscent of visiting their favorite coffee shop. The house offers 4 bedrooms, 1 full bathroom on the second floor & a half bath on the main floor. A portable crib is available for infants (30 1b max). Please note that we are in the process of having baseboards milled by a local crafts person who is also installing them when we are closed.

Family · Location · Kitchen

The MacArthur House

Four generations of our family have resided at The MacArthur House. Formally a farm house it is a quaint & charming home with many of its original features. The kitchen has a chalkboard that came from one of the local schools. The house is located in a quiet residential neighborhood in close proximity to the local schools,colleges & hospital. We are licensed. We love animals, but we do not invite pets to stay on our property. We also do not allow smoking, or tobacco anywhere on our property.

Family · Value · Quiet

Stunning Bark Point Home on Superior's South Shore

One of a kind, open/loft-concept (see pics: it really is open) artisan-crafted lake home on Superior's south shore: paddle in summer/ice hike in winter. Breathtaking sunsets. 300+ feet of private shoreline or short walk to public beach. Great kitchen. Up to 8 people and most dogs welcome - PET FEE: pets are an extra $25 (there is a place to leave this next to the house manual on the kitchen counter) Scenic huge patio with built-in fire pit (BYO firewood) We hope you love it as much as we do!

Value · Location · Kitchen

The I Love Lake Superior House

Your family will be close to everything when you stay at this centrally-located home. The decor and furnishings highlight all the AMAZING things this region has to offer: woods, water, islands, history, sea caves, rock hunting, food, nature, and fun! This recently updated home will be the comfortable and spacious home-base for your Chequamegon Bay adventures with 3 bedrooms, 2 full baths, a huge bright kitchen, a warm dining room, central A/C, electric fireplace, and a fully stocked kitchen.

Location · Family · Comfort

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.

Value · Location · Beach

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.

Value · Family · Accuracy

A Cozy Getaway in Ashland

Welcome to your perfect getaway! This cozy 2-bedroom, 1-bath home is centrally located just a short walk from downtown, a bakery, brewery, and two blocks from Lake Superior. Enjoy direct ATV/snowmobile trail access, relax on the deck, or gather around the firepit. Take a walk or bike ride along the scenic lake trail or explore nearby shops. Only 30 minutes from Bayfield and 90 from Duluth-perfect for day trips or a relaxing retreat.

Value · Location · Hiking

Back to the Old Farm

Welcome to Ashland..!! Relax and Enjoy an old fashion farmhouse setting on 17 acres out in the country with plenty of parking in the horseshoe curve driveway…and yet only 8 miles from Lake Superior in Ashland WI.!! Beautiful Copper Falls is about a 30 minute drive..9 miles from ABC raceway ..,, Three miles to Benoit Cheese Haus..6 bedroom older home uniquely decorated for you to relax and enjoy in a peaceful area,Welcome y’all!

Family · Location · Cleanliness

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.

Family · Location · TV

Coveside Cottage Waterside Pet Friendly Retreat

Your summer oasis awaits! Enjoy 8 private acres with sandy beach access on the quiet south shore of Lake Superior. Relax on the patio with a book or explore the lake with our kayaks and paddleboards. Minutes from Ashland, Washburn, and Bayfield, the cabin is an ideal home base for your group, featuring a well-appointed kitchen, Weber gas grill, covered patio, outdoor shower, and original charm with modern updates.

Location · Family · Outdoor spaces

Adventure Homebase

Built in 2019, this right-sized home sits on the very east edge of Ashland Wisconsin. Lake Superior is a short walk away. Set in the woods with huge windows, it feels like the most luxurious campsite you've experienced! Enjoy it as a homebase to come back to after adventuring on the lake, at the beach, hiking to waterfalls or wandering the other little towns along the Chequamegon Bay.

Value · Location · Accuracy

Guest House

The Guest House is located a 1/2 block from the Corridor snowmobile trail. It sits on a quiet residential street, walking distance to the grocery store and food and drink establishments. The Guest House has off street parking and room to bring a trailer. It is a two bedroom one bath single level home built in 2023.

Value · Location · Kitchen