Holiday houses in Eileen

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Eileen

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

1 of 1 pages1 / 1
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.

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, 104 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
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.
Guesthouse in Ashland
4.99 out of 5 average rating, 410 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 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 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, 187 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
4.88 out of 5 average rating, 161 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.

Guest favourite
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, 400 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.

Top Guest favourite
The image depicts a sandy shoreline bordered by smooth, dark stones along a calm bay. Lush greenery lines the water’s edge, with scattered trees in the background. The overcast sky creates a serene atmosphere, inviting peaceful walks along the beach.
Guesthouse in Ashland
4.92 out of 5 average rating, 78 reviews

Beach Front Hideaway

Private beach with spectacular views. Kayaks available for a paddle out in the bay or enjoy a sunset from the deck. Also 2 bikes, fishingpoles, deck heaters, gas grills and a fire pit w/wood. Or Curl up with a good book in front of the indoor fireplace. 1 bed, 1 high end sofa sleeper. TV and Wifi, and a complimentary bottle of wine. A great retreat for 2 couples or a small group of friends. Only 8 minutes from downtown Ashland.

Superhost
Farm stay in Ashland
4.93 out of 5 average rating, 14 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
Cabin in Bayfield
4.97 out of 5 average rating, 178 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.

Guest favourite
Historic buildings line the street, showcasing a blend of architectural styles with colorful facades. A clear blue sky complements the vibrant storefronts, which feature signage and awnings. Local shops are visible, highlighting the charm of Ashland's Main Street Historic District.
Apartment in Ashland
4.97 out of 5 average rating, 221 reviews

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.

Popular amenities for Eileen holiday rentals