Holiday rentals in Eileen

4.94 out of 5 average rating, 284 reviews

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

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

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

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, 366 reviews

Guest house 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

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

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

Apartment 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

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

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

Flat 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!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Eileen holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Eileen

4.96 out of 5 average rating, 57 reviews

Farm stay in Ashland

Cozy Farm Retreat - minutes to Ashland

TonyaRating, 5 stars2 days ago

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

4.93 out of 5 average rating, 46 reviews

Cabin in Washburn

White Wings Cottage

LauraRating, 5 stars5 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

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

Home in Iron River

Guest House

MaryRating, 5 stars5 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

Home in Ashland

Rustic Cabin Retreat

TinaRating, 5 stars8 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

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

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!