Holiday rentals in Eileen

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Top-rated holiday rentals in Eileen

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Top guest favourite
The cabin exterior features a white facade with blue roofing. A well-maintained grassy area surrounds the structure, and a noticeable flagpole stands nearby. Views of Chequemegon Bay can be seen in the background, highlighting the tranquil water and sky.
Cabin in Ashland
5 out of 5 average rating, 22 reviews

"Our Cabin" on Lake Superior

FISHERMEN/FAMILIES/FRIENDS “Our Cabin” is perfect for your getaway or for fishing and boating, less than 1 min from a no-fee boat launch. Private boat parking with circle driveway. Located on Chequemegon Bay, less than 10 min from Ashland, built in the 50's, our family of 6 spent 33 summers in this 600 sq ft cabin. Two twin beds in the br and a queen sized murphy bed pulls down in the living area. Recently remodeled, completely updated, conveniently located to Bayfield and the Apostle Islands.

Guest favourite
The exterior of The MacArthur House is displayed, showcasing a three-story structure with light-colored siding and a brown roof. A wooden porch is seen, surrounded by a garden. A colorful play structure is located on the lawn, indicating a family-friendly space.
Home in Ashland
4.83 out of 5 average rating, 105 reviews

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.

Top guest favourite
A private deck features a glass table surrounded by two chairs with cushions, complemented by vibrant planters. In the background, a lush garden blooms with various flowers and greenery, creating an inviting outdoor retreat.
Guest suite in Brule
4.98 out of 5 average rating, 215 reviews

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.

Top guest favourite
The cabin's exterior displays a modern A-frame design, surrounded by a lush forest. The patio area features blue adirondack chairs and a small table, inviting relaxation amidst nature. A circular window enhances the aesthetic, creating a connection between indoor and outdoor spaces.
Cabin in Bayfield
4.99 out of 5 average rating, 223 reviews

The Acorn of Little Sand Bay Dog Friendly

Modern-rustic, Aframe on 10 wooded acres; beautiful, simple décor, fully equipped kitchen, glass stove top, air-fryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, with a heated tile floor, walk-in shower. Towels, shampoo/conditioner/bodywash are provided. King bed in loft and NEW king gel memory foam bed on main floor. Smart TV, wi-fi. Woodstove heats the cabin perfectly as the main heat source. All wood is provided for woodstove and firepit. There is a minisplit heat/ac unit.

Top guest favourite
A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.
Guest house in Ashland
4.99 out of 5 average rating, 413 reviews

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.

Top guest favourite
A newly constructed cabin sits nestled among trees, featuring large picture windows and a screened porch. Nearby, a barrel sauna adds a rustic touch to the serene forest setting, with soft sunlight filtering through the treetops.
Cabin in Cornucopia
5 out of 5 average rating, 152 reviews

Romantic Forest Cabin, Sauna, Trail to Beach

Treat yourself to a deluxe stay in this quiet, newly constructed cabin with picture windows, screened porch and barrel sauna. Enjoy long days and sunsets at Corny Beach, a 10 min walk from the cabin along a nature trail. Visit Bayfield 20 min away or take in the quirky, small-town of Cornucopia and then come home and take a sauna in this peaceful forest! The cabin has an occupancy limit of 2 adults and one dog ($50 pet fee). A SUP board is stored near the beach for guests in summer.

Top guest favourite
The exterior of the storage container unit is showcased in a serene setting, featuring large windows and a sleek black facade. The surrounding area is landscaped with grass and bordered by a stone path, under a sky painted with soft hues of sunset.
Shipping container in South Range
4.98 out of 5 average rating, 227 reviews

Sölveig Stay: Shipping Container with Nordic SAUNA

Storage containers converted into a Nordic sauna and living space. Set in the woods half a mile from the sandy south shore of LAKE SUPERIOR. Our two-person occupancy and minimal design are curated to re-focus and re-fresh its inhabitants. Located on 80 acres of private land, you will fall in love with the peace and quiet. Whether you’re looking for a romantic couples getaway, spa weekend, or workspace as a digital nomad, Sölveig Stay was designed to spark creativity and relaxation.

Top guest favourite
The A-frame cabin is nestled among trees, showcasing a vibrant wooden exterior and a sloped metal roof. Sunlight filters through the foliage, creating a serene and inviting setting. The surrounding area features large rocks and a gravel pathway, enhancing the peaceful atmosphere.
Cabin in Hayward
4.99 out of 5 average rating, 150 reviews

Seeley Oaks A-Frame | Secluded Retreat on 40 Acres

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. At 700sq ft, it's intended for two adults, with the option of 2 addtl kids. A queen bed in the loft, in-floor heat, full kitchen, gas fireplace, and washer and dryer. Less than 2 mi from Highway 63, 8 mi from Cable, and 10 mi from Hayward. IG: @Seeleyoaks

Guest favourite
A bright living area features a comfortable gray sofa complemented by a round area rug. A wooden coffee table sits in front of a TV mounted on the wall. Natural light streams through a large bay window, enhancing the welcoming atmosphere.
Apartment in Ashland
4.88 out of 5 average rating, 164 reviews

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.

Superhost
A rustic red yurt is surrounded by a forest of trees. A large wooden deck offers a welcoming entrance and is equipped with a sturdy railing. Natural ground covers and underbrush can be seen nearby, creating a serene and natural setting.
Yurt in Bayfield
4.95 out of 5 average rating, 402 reviews

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.

Superhost
Farm stay in Ashland
4.87 out of 5 average rating, 15 reviews

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!

Top guest favourite
Home in Iron River
4.98 out of 5 average rating, 105 reviews

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.

Popular amenities for Eileen holiday rentals