Holiday rentals in Eileen

4.87 out of 5 average rating, 235 reviews

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, 169 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.

4.99 out of 5 average rating, 103 reviews

Cabin in Hayward

Seeley Oaks A-Frame | Quiet, 40 Acres, Near Trails

This is a cabin-in-the-woods experience! The Seeley Oaks A-Frame is our slice of the peaceful Northwoods experience. It's on 40 private, tranquil acres (no neighbors!) with great access to all the Hayward-Cable area has to offer. It's small - intended for two adults, with the option of 2 addtl kids. It's a total of 700 sq ft, with a queen bed in the loft, in-floor heat, full kitchen, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

4.88 out of 5 average rating, 155 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.)

4.99 out of 5 average rating, 368 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.

4.79 out of 5 average rating, 159 reviews

Apartment in Bayfield

One Minute Walk to Lake Superior. Brookside #10

Amazing location! This Comfy Studio Condo sleeps 4, King bed & Queen sofa sleeper. kitchen, balcony, AC, CableTV, Strong WiFi, BBQ, fire pit, jet-tub/shower. Walk to the restaurant, bar, marina and pool. The pool opens in July. Brookside is 2.3 miles from Bayfield. Hike or bike the Brownstone trail along the lake. Ride the ferry to Madeline or cruise the Apostles. Sail, fish, kayak, golf, orchards, ski. Mt Ashwabay, Big top , Bayview beach plus many trails within minutes.

4.87 out of 5 average rating, 156 reviews

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, 348 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, 199 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, 189 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, 108 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 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 stars1 week ago

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

5 out of 5 average rating, 49 reviews

Home in Iron River

Guest House

JessicaRating, 5 stars5 days 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.

4.78 out of 5 average rating, 9 reviews

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!

4.86 out of 5 average rating, 65 reviews

Hidden Vines - Walkable To Murals - Dog-Friendly

IanRating, 5 stars1 month ago

Perfect stay! Cute, clean and cozy home!

4.92 out of 5 average rating, 25 reviews

Chalet in Washburn

Hilltop Log Cabin| Valley Views Near ATV trails

DavidRating, 5 stars5 months ago

We had a wonderful time here! Walking in the woods, sitting by the fire, exploring the nearby towns - a perfect escape. Kevin was very responsive, which I deeply appreciated.

4.82 out of 5 average rating, 50 reviews

Cheerful three-bedroom home with free parking

JoeRating, 5 stars1 week ago

This was a great house to stay at, plenty of space and amenities. We did not really use the basement but it was nice to have the extra space available. It was nice that they now have a Weber gas grill, we made good use of it. Great central location to explore the a Apostle Islands and the UP.