Holiday houses in Eileen

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Top-rated holiday rentals in Eileen

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 536 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
The Main Cottage is surrounded by a tranquil winter landscape, with a blanket of snow covering the ground and trees. The cozy exterior features a spacious wrap-around deck and large windows that allow for natural light, set against a serene backdrop of woods.
Cottage in Bayfield
4.99 out of 5 average rating, 106 reviews

Bayfield Fruit Loop Retreat - Main Cottage

Welcome to the Bayfield Fruitloop Retreat, featuring a beautiful "Main Cottage" nestled in 7 acres of woods in Bayfield, Wisconsin. The property allows you to savor a peaceful & quiet northwoods experience but still minutes from several attractions & historic downtown Bayfield. The property is conveniently located just 5 minutes' drive or 2.5 miles from the center of downtown Bayfield. Located right on country Hwy J, a starting point for a self-guided tour around the city of Bayfield where a

Top Guest favourite
Cabin in Hayward
4.98 out of 5 average rating, 132 reviews

Seeley Oaks A-Frame | Couples Winter Getaway

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

Guest favourite
A rustic cottage is surrounded by colorful autumn foliage, showcasing its wooden exterior and A-framed roof. A large porch with steps provides entry, and a pathway leads through the grassy yard, where scattered leaves complement the natural setting.
Cabin in Port Wing
4.8 out of 5 average rating, 119 reviews

Cozy South Shore cottage near Lake Superior

Enjoy the splendor of Lake Superior at our cozy, rustic cottage near Port Wing, WI. Situated halfway between Duluth/Superior and Bayfield, it's the perfect location to visit all your favorite South Shore locations. There's no need to choose between privacy & the difficulties of accessing remote properties. Our cottage is located within 68 acres of private, wooded wilderness. Yet since we're next to the Wisconsin Lake Superior Scenic Byway (Hwy 13), it's easy to get wherever you want to go!

Guest favourite
A spacious yard is shown, featuring a single-story house with large windows, alongside a red shed. Green trees provide shade, and a vehicle is parked in the gravel driveway. A propane tank is visible near the edge of the property.
Home in Iron River
4.86 out of 5 average rating, 140 reviews

Wade Inn Iron River

The Wade Inn Iron River is a great place to relax and enjoy the quiet beauty of nature and be less than a half mile from town! Very peaceful setting on a quiet wooded lot with lots of shade trees and outdoor table and chairs with a Grill!! Iron River is also a great location, close to National Forests, the World famous Brule river, and Lake Superior all within a fifteen minute drive!! Bayfield and the Apostle Islands are also not too much further, and are great easy day trips to enjoy.

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.
Guesthouse in Ashland
4.99 out of 5 average rating, 396 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
The cottage exterior features a wooden entrance with a small deck, surrounded by a snowy landscape. Icicles hang from the eaves, and evergreen trees are visible nearby. Window boxes adorned with greenery add a touch of charm to the entrance.
Cottage in Cornucopia
4.99 out of 5 average rating, 151 reviews

Borealis Cottage by Siskiwit Bay

Borealis Cottage sits on a 2-acre, private, wooded lot in the sustainably designed Sawgrass Community of Cornucopia. Light-filled cottage with open floor plan includes a sleeping loft, screened porch, gas fireplace, and fully-equipped kitchen. A quick, quiet walk from the cottage takes you to a private wooded path with access to Cornucopia Beach on Siskiwit Bay. Explore the Apostle Islands National Lakeshore--our cottage is located 4 miles from Meyers Beach and 20 miles from Bayfield.

Superhost
The tranquil surface of Lake Delta is visible, reflecting a partially cloudy sky. Wooden docks extend into the water, with gently rippling waves nearby. Trees line the distant shore, contributing to the natural landscape surrounding the lake.
Cabin in Iron River
4.75 out of 5 average rating, 212 reviews

Lake Delta Deer Trail Delight

Deer Trail Cabin 6 is on the shore of Lake Delta in the heart of Delta. Popular day trips include the Hayward lakes area, the Apostle Islands National Lakeshore and Bayfield or exploring the endless trails, waterfalls and wilderness within Bayfield County. This is a furnished two bedroom cabin with full kitchen and bath. Great view of Lake Delta and next to swimming beach. There is direct ATV trail access from your cabin but we ask that you do not ride around the property.

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, 171 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.
Condo in Ashland
4.89 out of 5 average rating, 148 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 red two-story house with a green metal roof is set within a natural landscape. A gravel driveway leads up to the home, which features several windows and a large yard. A parked blue car is positioned near the entrance.
Home in Washburn
4.74 out of 5 average rating, 385 reviews

The Red Onion House near Bayfield

Located 10 minutes s. of Bayfield, this is a casual, comfortable, and welcoming two-bedroom located across the highway from Lake Superior and the Apostle Islands and less than a mile from near the best beaches in the region. Named for the Onion River that flows nearby, this rental has a combo of pine floors & tile. Upstairs kitchen & dining area. Large lawn with easy, plentiful parking. Mt. Ashwabay, Big Top Chautauqua nearby. Outdoor patio + campfire area.

Top Guest favourite
A Scandinavian-style cabin is elevated among autumn trees, showcasing a welcoming, rustic exterior. Two Adirondack chairs are positioned around a fire pit, which is surrounded by a circle of smooth rocks. The forest setting adds a serene backdrop to this outdoor gathering space.
Cabin in Bayfield
4.97 out of 5 average rating, 160 reviews

Romantic Vineyard Cabin, Sauna, Plunge Pool

Come and celebrate all that Bayfield has to offer at this quiet vineyard and forest getaway, just 2 miles from downtown. Located in Bayfield's charming Fruit Loop, you'll be surrounded by vines, forest, orchards, and berry farms. The Scandinavian cabin, forest facing sauna with plunge pool, and vineyard sit within acres of secluded woods. The cabin has an occupancy limit of 2 adults and one dog. There is a $40 pet fee.

Popular amenities for Eileen holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Bayfield County
  5. Eileen