Holiday rentals in Eileen

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Top-rated holiday rentals in Eileen

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Guest favourite
A comfortable living room displays a blue sofa with decorative pillows, positioned across from a wooden dresser and a mirror. Natural light enters through large windows, with light curtains. A small round table sits in the center, and a rocking chair is placed nearby, enhancing the cozy atmosphere.
Cottage in Ashland
4.82 out of 5 average rating, 71 reviews

Cottage 12 - Mission Springs Resort

If you're looking for a relaxing getaway you've found it! We love this cottage because it sits right on top of the hill leading down to the lake-there is nothing like an early morning stroll, coffee in hand, down to the beach. The bedrooms have old-fashioned windows that hook to the ceiling when they are open--letting in the sound of the waves hitting the beach (one of which is just down the hill from your front door). You are 20 minutes from Bayfield and the Apostle Islands. Take a ferry ride to Madeline Island, rent kayaks and tour the sea caves, or watch the sunset while on an Apostle Islands boat tour. You have found the launching point for the vacation you will never forget! Eat in kitchen. Living room with Direct TV. Plenty of parking for boats or ATV's. Very close to the best little tourist town of Bayfield and the Apostle Islands. Perfect place to vacation. Fun for the whole family.

Superhost
A yurt is nestled among trees, featuring a circular white top and green walls. A small wooden deck extends from the entrance, providing a welcoming outdoor space. The surrounding area is landscaped with lush greenery and scattered underbrush.
Yurt in Bayfield
4.88 out of 5 average rating, 551 reviews

Bayfield Rustic Yurt 1 (Evergreen)

Explore thousands of acres of the Bayfield County Forest and enjoy endless miles of exceptionally maintained non-motorized recreational trails. The yurt has direct access to CAMBA mountain bike trails and Mt. Ashwabay ski trails. The landscape is also spectacular. Take in the panoramic views of Lake Superior and the Onion River valley. This is a rustic, minimally maintained yurt set in the middle of the county forest, so come prepared to relax, unwind and explore the wonders of the north woods.

Top guest favourite
Cabin in South Range
5 out of 5 average rating, 38 reviews

Sölveig Sentō: Private Forest Spa - Sauna & Plunge

Nordic soul meets Japanese ritual in a 100-year-old hunting shack, reborn. Cedar sauna, cold plunge, shower room, soaking tub and full, integrated living areas from a cohesive private retreat. Set on 55 secluded acres in South Range, Wisconsin—20 minutes from Duluth and 1.5 miles from the sandy shores of Lake Superior. More than accommodation, Sentō offers unhurried space for restoration: heat, cold, immersion, repeat. A deliberate pause. A private ritual. Zero time limits. Zero strangers.

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, 224 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, 414 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.

Guest favourite
Cabin in Drummond
5 out of 5 average rating, 12 reviews

Lundy's Black Bear Motel - Lemgrove

Multi-Room Daily Discounts - 3% (2 Rooms), 5% (3 Rooms). Weekly - 5% (2 Rooms), 8% (3 Rooms) Newly remodeled and nestled in the heart of the Chequamegon National Forest. Enjoy direct access to UTV and snowmobile trails, plus nearby fishing, hunting, skiing, and local events. Clean, comfortable rooms and true Northwoods charm make this the perfect base for your next adventure. Relax by the firepit, explore scenic trails, and experience the friendly small-town hospitality of Drummond.

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, 153 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.

Guest favourite
The exterior of the townhouse is framed by lush green foliage and towering trees. The two-story structure, with a dark wood façade, features multiple windows and a red front door. A covered entrance leads to a staircase, while a pathway is lined with natural stones.
Townhouse in Cable
4.93 out of 5 average rating, 150 reviews

Great outdoor retreat in the North Woods.

Valhalla Townhouse is just a few miles outside the cute town of Cable Wisconsin. This property sits adjacent to an old ski hill and walking distance from the American Birkebeiner Trail head. Miles of trails are just out your door for cross country skiing, mountain biking, snowmobiling, hiking and ATV's. There are also numerous lakes in the area and the beautiful Namekagon river for fishing or canoeing. There is something for everyone here at Valhalla! We hope you enjoy your stay!

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, 151 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 small wooden dining table is positioned against the wall, accompanied by two white, spindle-back chairs. A light plaid table runner is placed across the table. Natural light filters in through a nearby window, creating a warm and welcoming dining space.
Home in Ashland
4.87 out of 5 average rating, 189 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.

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, 165 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
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!

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