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Holiday rentals in Ashland County

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Top-rated holiday rentals in Ashland County

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Apartment in Bayfield

4.83 out of 5 average rating, 69 reviews

Downtown Bayfield 2 BR Condo fireplace sleeps 6

Perfect for a long weekend get-away or extended stay in Bayfield. Cozy two bedroom condo located right downtown. Boatworks is the only condo in town with an elevator. Walk to all the famous Bayfield restaurants and Saloons. (Most only a 2-3 blocks from condo) . Lake Superior across the street. Explore the City Dock, 2 Marinas, ferry to Madeline Island, local golf coarse, fish charters, sail boating, Apostle Islands National Lake Shore (22 islands). 5 star Orchards surround Bayfield.A must tour.

Guest favourite

Flat in Ironwood

4.86 out of 5 average rating, 44 reviews

Frosted Lakes-Upscale Efficiency

An unforgettable smaller apt packs a punch for its size, hotel quality Perfect for single person or couple or traveling nurse to renew and relax, fishing, waterfalls, skiing or snowmobiling. Dual power leather recliner with power lumbar back support & headrests for movie night on 55" HD Samsung Smart TV Fresh towels always available at no additional cost. Total luxury renovation that may surprise you and want to visit again and again. Book for best fall availability. Dog weight restriction

Guest favourite

Home in Bayfield

5 out of 5 average rating, 13 reviews

Private Spot W/ Madeline Island/Lake Views & Sauna

-Modern, Spacious & Bright w/Great Vibes -Ideal Spot atop Bayfield on 1.56 Acres -Views of Madeline Island & Bayfield -Spacious lower level equally bright & airy -On a dead end street w/Ample parking -TV in each bedroom -Gateway to Apostle Islands -Near Downtown Bayfield & Marina - Wood-burning fireplace -Bonus lounge Room W/ a 65-inch TV, Bean Bags & board games - Fully equipped kitchen - Spacious Primary Bedroom W/ en-suite Bathroom & Deck Access **Special Pricing For Monthly/weekly stays

Guest favourite

Chalet in Upson

4.86 out of 5 average rating, 44 reviews

AlpenhausWI Whitecap, Upson WI Waterfalls Hike Ski

Located at Whitecap Mountains Resort, a recreational wonderland! Near Hurley/Ironwood, MI. Easy access to ski hill , lake for fishing, 22 waterfalls within 30 miles. A quiet retreat with lots of windows! New mattresses, linens, updated baths, functional kitchen. Fireplace, outdoor decks, large comfortable space. Duplex with private entry. PLEASE NOTE: Whiteccap Mountains Resort is currently undergoing remodeling and the hotel, pool, hot tub and golf course are not open at this time.

Guest favourite

Flat in Bayfield

4.96 out of 5 average rating, 71 reviews

The Blue Grotto in the heart of Bayfield

The Blue Grotto is an upper level, fully furnished, 1-bedroom, 3/4-bath luxury apartment with private entrance in the heart of downtown Bayfield within walking distance to the ferry, restaurants, shops and beaches. Private deck with lake view. Sleeps 4. Private bedroom has Cal king bed; living room has Murphy bed. Free designated alley parking. A/C available. In-floor heat. Hardwood floors and natural stone tile throughout. Reliable Wi-Fi. Available year round. Check in 3PM; check out 11AM.

Guest favourite

Apartment in Bayfield

4.94 out of 5 average rating, 87 reviews

Lakeview Condo: Downtown Bayfield, Beach, Deck

Experience the charm of Bayfield in our spacious top-floor condo with breathtaking views of Lake Superior. Perfectly situated, it's an ideal spot for sunrise enthusiasts & offers quick access to downtown. Enjoy the comfort of modern living in a serene lakeside setting. Walk to shops, restaurants, & the island ferry, or relax on the deck overlooking the lake. • 3 bedrooms + loft, sleeps 8 • 2.5 bath, fully stocked kitchen • Deck w/ dining table • Smart TV w/ streaming • Washer/dryer

Apartment in Bayfield

4.92 out of 5 average rating, 12 reviews

Clean Modern Beach Front Condo with Lake Views

Enjoy stunning Lake Superior views in this clean and modern 1 bedroom + loft condo that is literally steps from the beach! The unit features clean and updated spaces throughout, a queen-size mattress in the bedroom, a loft with two additional twin beds, comfy living room furniture from which to enjoy the incredible lake views, and an electric fireplace that adds coziness to the space. You'll also be able to enjoy the private balcony overlooking the lake & beach, which are just steps away.

Guest favourite

Townhouse in Bessemer

4.96 out of 5 average rating, 27 reviews

Chic, Cozy, Spacious! ~ Drift-Away Lodge 2

What makes us special? ~ Pamper friendly - Stylish, modern amenities and decor with high quality king and queen sized beds so you can relax and feel pampered ~ Skier / OTV'er / Snowmobiler friendly - we have ski racks, boot trays, boot warmers, crock pots, fuzzy blankets ~ Family friendly - we have baby gear, board games, outdoor grill, and multiple TV's ~ Pet friendly - You are welcome to add a dog to your reservation, we have a pooch pouch of supplies for you to use during your stay

Guest favourite

Flat in Hurley

4.89 out of 5 average rating, 44 reviews

Hurley: location for all hobbies, holidays, events

Your family will be close to everything when you stay at this centrally-located place. Two bedroom rental unit with large parking area in back for trucks and trailers 2 queen beds 1 sectional couch -1 block from silver street with many food and bar options. -On the ATV/ snowmobile trail -2 blocks from Iron Belle walking trail -Many cross country ski trails nearby -blackjack/Indianhead ski resort 13 miles. -Whitecap Mountain ski resort 13 miles - Powderhorn ski resort 10 miles.

Guest favourite

Home in Bessemer

5 out of 5 average rating, 14 reviews

Mountain Top Chalet ~ Your Adventure Base Camp!

Located right off Big Powderhorn's Lift 1, Mountain Top Chalet has everything you're looking for in a vacation rental! Tucked into the woods and fully remodeled with your comfort in mind, this private, beautiful home has everything you could want and more! There are 3 levels to this home, 2 living spaces each with a wood burning fireplace, 4 comfy bedrooms and a large loft area dedicated to hosting kids. This home is perfect for large group getaways at any time of the year!

Guest favourite

Chalet in Bessemer

4.94 out of 5 average rating, 233 reviews

Hot Tub! Fireplace! The Wüdenknipple - Powderhorn

My place is located at Big Powderhorn Ski Resort and close to Lake Superior, family-friendly activities, great views, restaurants and dining. You’ll love my place because of the location, the ambiance, the outdoor space, and the neighborhood. My place is good for couples, solo adventurers, and families (with kids). Outdoor Hot Tub! Wood burning Fireplace with wood supplied! Great cell service! TV, Cable, Roku, WIFI....great entertainment! Washer/Dryer

Guest favourite

Cottage in Upson

4.95 out of 5 average rating, 60 reviews

Stunning 3 bed, 2 bath private lake front cottage.

Take it easy at this unique and tranquil getaway. All season property in wooded setting. Ski-in/ski-out access to Whitecap Mountain, snowmobile trails and ice fishing. Cottage is nestled on the hills of whitecap Mountain overlooking Weber Lake where you can kayak, swim or fish. Winter access requires 4 wheel drive. Public use of the indoor pool for a nominal daily fee in the Whitecap hotel is available nearby.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Ashland County holiday rentals

Free parking on premises

Air conditioning

Other great holiday rentals in Ashland County

Guest favourite

Home in Ironwood

4.81 out of 5 average rating, 215 reviews

Cheerful 2 bedroom home away from home

Guest favourite

Home in Ashland

4.95 out of 5 average rating, 37 reviews

Adventure Homebase

Townhouse in Wakefield

4.88 out of 5 average rating, 51 reviews

SnowRiver Resort Condo ski in/out-(Indianhead Mtn)

Guest favourite

Home in Bayfield

4.94 out of 5 average rating, 18 reviews

Brickyard Lakeside Retreat

Guest favourite

Home in Bessemer

4.96 out of 5 average rating, 28 reviews

Beautiful 4 season getaway in the Western UP of MI

Guest favourite

Apartment in Ironwood Township

4.95 out of 5 average rating, 19 reviews

Cozy home away from home #4 Schnickelfritz

Guest favourite

Cabin in Gurney

5 out of 5 average rating, 67 reviews

Potato River Falls Log Cabin Retreat 130 Acres

Guest favourite

Home in Ironwood

4.91 out of 5 average rating, 23 reviews

Cheerful 4-bedroom home with a hot tub

Destinations to explore