Vacation rentals in Eileen

4.87 out of 5 average rating, 235 reviews

A green hutch is positioned in the kitchen, showcasing a selection of cookbooks and decorative items. The open space leads to the living and dining area, featuring wooden flooring and a welcoming atmosphere.

Home in Ashland

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.

4.97 out of 5 average rating, 167 reviews

A donkey grazes on lush grass in a serene wooded area. Surrounding dandelions dot the grassy landscape, while the foliage provides a natural backdrop. A low wooden fence, comprised of branches, is positioned in the foreground, enhancing the tranquil rural setting.

Guest suite in Brule

The Bee's Balm

You'll find us tucked in the quiet woods of northern WI near the Brule River. We're remote enough to experience star-filled skies & fireflies, but not far from many premier attractions. Your space is a self-contained apartment on the lower level of our 2.5 story home. It features a private entry, queen-sized bed, kitchenette, lower level private deck, access our beautiful grounds & more! We're a family of artists who love to travel & to introduce others to our beautiful part of the world.

A clean, simple bathtub is shown, enclosed by a white curtain. The tub features a textured bottom for safety and a sleek faucet on the side. A decorative stone mat lies on the floor, providing a natural touch to the bathroom.

4.84 out of 5 average rating, 121 reviews

Wade Inn Iron River

The Wade Inn Iron River is a great place to relax and enjoy the quiet beauty of nature and be less than a half mile from town! Very peaceful setting on a quiet wooded lot with lots of shade trees and outdoor table and chairs with a Grill!! Iron River is also a great location, close to National Forests, the World famous Brule river, and Lake Superior all within a fifteen minute drive!! Bayfield and the Apostle Islands are also not too much further, and are great easy day trips to enjoy.

4.88 out of 5 average rating, 155 reviews

The sleeping area features two sets of wooden bunk beds with plaid mattresses. A neutral-colored rug lies on the floor, surrounded by floral-patterned edges. Natural light enters through a small window, creating a bright and functional space for guests.

Cabin in Bayfield County

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.)

4.75 out of 5 average rating, 137 reviews

A tranquil lake scene is captured at twilight, reflecting soft colors of the sky. A dock with multiple boat slips extends into the water amidst lush trees lining the shore. The stillness of the water enhances the serene atmosphere.

Cabin in Iron River

Iron River, WI. Deer Trail Cabin #2 (Lake Delta)

Enjoy the peace and quiet of northern Wisconsin in this cute, comfortable cabin overlooking beautiful Lake Delta near Iron River Wi. Nice deck with a picnic table, charcoal grill, lawn chairs, and a view of the lake. Enjoy the evening in front of the fire pit telling stories , enjoying a beverage, or roasting marshmallows with the kids. Perfect for families, atv riders, snowmobilers, fisherman and hunters. This is an old resort with 10 cabins, it can be busy during the peak summer season.

4.99 out of 5 average rating, 367 reviews

Two white Adirondack chairs are positioned around a fire pit, surrounded by lush greenery and tall trees. The open sky above features bright blue hues, offering a peaceful outdoor setting for relaxation near nature.

Guesthouse in Ashland

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.

4.87 out of 5 average rating, 155 reviews

A wooden bench is positioned along a scenic waterfront, facing a calm expanse of water. The shoreline is lined with a walking path, and distant hills can be seen across the bay. Two cylindrical bollards are present nearby, adding to the waterfront setting.

Home in Ashland

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.

4.9 out of 5 average rating, 116 reviews

The image captures a rocky shoreline meeting a calm body of water, with vibrant red cliffs rising from the lake. Green foliage crowns the cliff tops, creating a natural frame around the scene. Subtle waves can be observed gently lapping against the rocks.

Condo in Ashland

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.

4.95 out of 5 average rating, 347 reviews

A rustic yurt is situated on a wooden deck, surrounded by tall trees displaying autumn foliage. The expansive view reveals a serene Lake Superior, contrasting the vibrant colors of the forest below. The sky is overcast, enhancing the natural ambiance of the landscape.

Yurt in Bayfield

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

4.95 out of 5 average rating, 198 reviews

A bathroom features natural wood paneling, creating a warm atmosphere. A compact vanity with a sink is visible, complemented by a mirror above. A towel bar holds a multi-colored towel. Essential toiletries can be found on the countertop, adding convenience to the space.

Cabin in Washburn

The Long House

My place is close to Lake Superior and the Apostle Islands It is located 2 miles north of Washburn or 10 miles south of Bayfield. Peaceful country setting, the long house is a freshly remodeled mobile home. Sorry, no pets. I have increased the number of guests to six . There are 4 double beds in the cabin. If you are booking with more than 4 guests, please allow for this. Thanks you! Open June 1 - mid October

4.96 out of 5 average rating, 189 reviews

Historic buildings line the street, showcasing a blend of architectural styles with colorful facades. A clear blue sky complements the vibrant storefronts, which feature signage and awnings. Local shops are visible, highlighting the charm of Ashland's Main Street Historic District.

Apartment in Ashland

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.

4.96 out of 5 average rating, 107 reviews

Cottage in Ashland

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!

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Other great vacation rentals in Eileen

5 out of 5 average rating, 93 reviews

A sandy path winds through lush green grass, leading towards a tranquil body of water. The horizon is lined with dark clouds, reflecting soft hues of light as the day transitions to dusk.

Cabin in Cornucopia

Romantic Forest Cabin, Sauna, Trail to Beach

SaraRating, 5 stars2 weeks ago

We loved our stay here! Walkable to the beach and downtown. So much to do in this area as well; loved the list of local recommendations they provided. The space was clean, comfortable, and inviting. Very thoughtful and responsive hosts. Would highly recommend!

5 out of 5 average rating, 3 reviews

A spacious closet is equipped with metal wire shelving and a wooden hanging rod. Several hangers hang from the rod, and additional shelves provide ample storage for folded items or accessories. The walls are painted in a light color, enhancing the open feel.

Apartment in Ashland

4 bed 1.5 bath apartment!

LindseyRating, 5 stars10 months ago

Great place to stay if you are going to be doing activities in the area and everyone wants their own bedroom.

4.94 out of 5 average rating, 47 reviews

A wooden sauna features a circular design with multiple seating areas made of slatted wood. An open door reveals a scenic view of Lake Superior, framed by trees. The inviting interior showcases a natural wood finish, enhancing the serene atmosphere.

Cabin in Washburn

White Wings Cottage

KauriRating, 5 stars4 days ago

This place was absolutely incredible. It is so cozy and homey with everything you need! The views and beachfront are unbeatable! The grill, fire pits, kayak/paddle board all accessible to us made us not want to leave. It is so peaceful and well kept. The hosts went out of their way to recommend great food/drinks, check in on us, and even about the Strawberry moon that was rising one night. Could not recommend more!

A modern bathroom features a stylish vanity with a countertop, sink, and ample storage. Black fixtures contrast with the light wood cabinetry. A shower/tub combination is present, enclosed by a curtain with a subtle pattern. Soft lighting enhances the clean and functional atmosphere.

5 out of 5 average rating, 49 reviews

Guest House

JessicaRating, 5 stars1 day ago

Wonderful place to stay while up in the North Woods, only 30 minutes to Ashland and 50 to Bay Field. Iron River had restaurants that were actually pretty good and I am overall very happy with the stay. Perfect place for the four of us.

4.97 out of 5 average rating, 30 reviews

Cabin in Iron River

Hart Haven A-frame on Lake Millicent

CarrieRating, 5 stars2 months ago

This was my second stay at Hart Haven, it was so nice the first time that I knew I wanted to see if it was available for this trip. Emily and Derek are wonderful hosts! The home is always so inviting and homey. Very clean (and I'm a picky person) and they have thought of everything you could need for your stay away from home. So peaceful and relaxing. I will definitely be checking the availability of Hart Haven for my future stays in Iron River. Thank you Emily and Derek!

A modern bathroom features a spacious soaking tub and a glass shower enclosure. Natural light enters through a window, illuminating the marble walls. A toilet is positioned near the wall, with wooden flooring adding warmth to the space. A decorative basket complements the design.

5 out of 5 average rating, 21 reviews

Buskey Bay Cozy Home

KaitlinRating, 5 stars8 months ago

We absolutely loved our stay here!! The house was spotless and felt very clean! The kitchen was stocked with everything we needed to make meals. We used the jet tub every day, but take note that it takes about an hour and a half to fill up! And I had forgotten my shampoo/conditioner at home and realized too late that there was nothing at the house. So make sure to pack your own! Overall, it was the perfect place to escape with my family! A quiet, cozy getaway. We would definitely stay here again. Our kids were already asking when we’re coming back as we pulled out of the driveway:)

4.98 out of 5 average rating, 80 reviews

Home in Washburn

Explore Bayfield-Apostle Islands-Lake Superior

Eric And ErikaRating, 5 stars6 months ago

We enjoyed our "winter" stay at Sheryl's place. The kitchen is well set up for cooking meals and the living space is comfortable. The location is perfect for wandering around town, day excursions to the park, or across to Madeline Island.

A wooden deck with metal railings overlooks a tranquil lake surrounded by trees. A small dock with a boat is visible in the water, framed by lush greenery. A staircase leads down from the deck to the lakefront, enhancing the serene setting.