Vacation rentals in Eileen

4.94 out of 5 average rating, 284 reviews

Two hanging chairs are nestled around a tree, suspended from a wooden structure. A circular wooden table rests on the ground, providing a space to gather. The area is surrounded by tall trees and a natural ground covering of pine needles.

Cabin in Hayward

The Timberjack

Although it's a rustic homage to the lumberjacks and jills of yesteryear, this cabin includes many of the comforts we now enjoy including a queen bed, kitchenette with fridge, hot water, AC/heat, a Keurig coffeemaker, smart TV and charcoal grill. The Timberjack is surrounded by trees right on Lake Hayward and close to downtown Hayward. Launch your canoe just steps from the cabin, walk into town for lunch, or go hiking or skiing on the nearby trails, this cabin is nestled in the ideal location!

4.97 out of 5 average rating, 166 reviews

A landscaped garden area features a stone fire pit surrounded by metal chairs. Pathways meander through vibrant flower beds, leading towards a serene pond. Wooden benches are positioned nearby, under the dappled shade of trees, inviting relaxation in the natural surroundings.

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.

4.88 out of 5 average rating, 154 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.

4.97 out of 5 average rating, 219 reviews

A compact bathroom is equipped with modern fixtures. A shower with a clear curtain is positioned next to a toilet and a sink built into cabinetry. A small, light-colored mat is placed in front of the washer and dryer, while natural wood accents enhance the design.

Tiny home in Saxon

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

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, 188 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

4.96 out of 5 average rating, 57 reviews

A well-organized kitchen corner showcases a blend of rustic and modern elements. Open wooden shelves display cast iron cookware, glassware, and dishware, while a bowl of fresh fruit rests on a counter. A black mini fridge is positioned beneath the cabinets, enhancing functionality.

Farm stay in Ashland

Cozy Farm Retreat - minutes to Ashland

TonyaRating, 5 stars3 days ago

Fantastic Friendly Hosts! Beautiful and Unique! We will be back again!

4.93 out of 5 average rating, 46 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

LauraRating, 5 stars6 days ago

We loved our stay! This cottage is in a beautiful spot with an amazing private beach! I wish the weather had been more cooperative as we would have loved to try out the kayak and paddleboard that was available. The cottage is pleasantly eclectic with so many artful touches. The pictures and thoughtful choice of decor add to the charm. Huge bedroom with comfy bed, we relished listening to the loons call in the early morning hours.

4.85 out of 5 average rating, 93 reviews

A well-lit bathroom features a double vanity with a smooth countertop and ample storage below. A large mirror reflects the space, while spotlights above provide additional illumination. A soft rug lies beneath and a full-length mirror is situated nearby, enhancing the room's functionality.

Home in Iron River

Pine’s Retreat

MoniqueRating, 5 stars2 weeks ago

Had a great trip to Iron River WI! We go to Wisconsin frequently and Debbie’s place was perfect. She was very accommodating, and the house was spotless. It had everything and more than we needed for our trip. We will be back.

5 out of 5 average rating, 48 reviews

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.

Home in Iron River

Guest House

MaryRating, 5 stars6 days ago

We really enjoyed our stay. It is in the city but very peaceful location. No city noise at all. We will be staying there again.

4.78 out of 5 average rating, 9 reviews

A spacious wooden deck is shown, furnished with a set of black chairs and a dining table. A brightly colored umbrella provides shade, and a grill is positioned on one side. Lush greenery and trees surround the area, creating a natural setting.

Home in Ashland

Rustic Cabin Retreat

TinaRating, 5 stars9 months ago

The house was as advertised. It was cozy and comfortable. Very clean and tidy. The kitchen had everything we needed to make meals. The house is in a perfect location to take in Ashland and Bayfield County! Chelsie was a great communicator. I highly recommend this host and house!

4.95 out of 5 average rating, 41 reviews

An open kitchen features dark cabinetry and a smooth stone countertop. Shelves display various dishes and plants, while a stainless steel stove and refrigerator are included. Bright light filters in through a sliding glass door, which provides views of a snowy outdoor landscape.

Home in Ashland

Adventure Homebase

JeanineRating, 5 stars2 weeks ago

This home is a true beauty! The owner has created a lovely oasis with a keen sense of style. Everything was so homey and comfortable. We especially loved cooking in the well-appointed kitchen - top notch! The upstairs great room made us feel like we were in a light and bright treehouse despite being in the woods. It was hard to believe we were just minutes from downtown Ashland. Thank you, thank you for sharing such an amazing home with us (and will you come decorate our house, pretty please?)!!

4.97 out of 5 average rating, 30 reviews

An open living space features a modern leather sofa with tufted design, accompanied by two armchairs and a small side table. Expansive glass windows provide a view of the outdoors, enhancing the area’s natural light. A fireplace is positioned nearby, adding to the environment.

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!