Book Holiday Homes in Ashland

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Featured Holiday Homes in Ashland

Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat

Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat

Cable
When you a stay at this vacation home in Cable, you'll be on the waterfront, just steps from Lake Namakagon and Chequamegon National Forest.
Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

Ashland
A stay at this vacation home places you in the heart of Ashland, within a 10-minute walk of Lake Superior and Ashland Mural Walk.
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Private Beach and Endless Water

Private Beach and Endless Water

La Pointe
With a stay at this vacation home in La Pointe, you'll be on a lake, within a 10-minute drive of Lake Superior and Big Bay State Park.
Private Beach and Endless Water
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Michigan Suite @ The Bayfield Guest House

Michigan Suite @ The Bayfield Guest House

Bayfield
The price is AU$410 per night from 19 Aug to 20 Aug
AU$410
19 Aug - 20 Aug
includes taxes & fees
A stay at this vacation home places you in the heart of Bayfield, within a 10-minute walk of Lake Superior and Bayfield Heritage Museum.
Michigan Suite @ The Bayfield Guest House
Paradise Shores & Fish Galore ~your own private beach & dock!

Paradise Shores & Fish Galore ~your own private beach & dock!

Cable
When you a stay at this vacation home in Cable, you'll be on the waterfront, just steps from Lake Namakagon and Chequamegon National Forest.
Paradise Shores & Fish Galore ~your own private beach & dock!
Sunshine  House | Historic Bayfield Farmhouse

Sunshine House | Historic Bayfield Farmhouse

Bayfield
When you stay at this vacation home in Bayfield, you'll be on a lake, within a 5-minute walk of Lake Superior and Bayfield Heritage Museum.
Sunshine House | Historic Bayfield Farmhouse
Newly remodeled lake home ! Steps away from the beautiful pike lake chain

Newly remodeled lake home ! Steps away from the beautiful pike lake chain

Iron River
When you stay at this vacation home in Iron River, you'll be on a lake and 6 minutes by car from Chequamegon National Forest.
Newly remodeled lake home ! Steps away from the beautiful pike lake chain
Great place for a Wonderful Northern Wisconsin  get away!!

Great place for a Wonderful Northern Wisconsin get away!!

Iron River
With a stay at this vacation home, you'll be centrally located in Iron River, 17.3 mi (27.9 km) from Lake Superior and 6.9 mi (11.1 km) from Chequamegon National ...
Great place for a Wonderful Northern Wisconsin get away!!
Beachfront and  Lakehouse With All of the Comforts!

Beachfront and Lakehouse With All of the Comforts!

Herbster
With a stay at this vacation home in Herbster, you'll be on the beach, within a 10-minute drive of Lake Superior and Bark Bay Slough State Natural Area.
Beachfront and Lakehouse With All of the Comforts!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Ashland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Ashland vacation homes are the perfect way for you to wing it.

Holiday houses in Ashland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Ashland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Ashland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Ashland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Ashland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Ashland Holiday Homes essential information

Accommodation
188 Holiday Homes
Lowest Price
AU$250
Highest Price
AU$410
Popular accommodation
Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat, Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior, Private Beach and Endless Water , Michigan Suite @ The Bayfield Guest House, Paradise Shores & Fish Galore ~your own private beach & dock!, Sunshine House | Historic Bayfield Farmhouse, Newly remodeled lake home ! Steps away from the beautiful pike lake chain, Great place for a Wonderful Northern Wisconsin get away!!, Beachfront and Lakehouse With All of the Comforts!

Top trending hotels in Ashland

AmericInn by Wyndham Ashland

AmericInn by Wyndham Ashland

2.5 out of 5
3009 Lakeshore Drive East, Ashland, WI
The price is AU$320 per night from 7 Sept to 8 Sept
AU$320
7 Sept - 8 Sept
includes taxes & fees
When you stay at AmericInn by Wyndham Ashland in Ashland, you'll be next to a golf course, just steps from Lake Superior and a 2-minute drive from Bayview ...
AmericInn by Wyndham Ashland
Cobblestone Inn & Suites - Ashland

Cobblestone Inn & Suites - Ashland

2.5 out of 5
818 Main Street W., Ashland, WI
A stay at Cobblestone Inn & Suites - Ashland places you in the heart of Ashland, steps from Lake Superior and Ashland Mural Walk.
Cobblestone Inn & Suites - Ashland
Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland

2 out of 5
1610 Lake Shore Dr W, Ashland, WI
Fully refundableReserve now, pay when you stay
The price is AU$250 per night from 8 Sept to 9 Sept
AU$250
8 Sept - 9 Sept
includes taxes & fees
With a stay at Super 8 by Wyndham Ashland in Ashland, you'll be within a 5-minute drive of Ashland Mural Walk and Ashland Historical Museum.
Super 8 by Wyndham Ashland
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Quality Inn Ashland - Lake Superior

Quality Inn Ashland - Lake Superior

2.5 out of 5
30600 Us Highway 2, Ashland, WI
The price is AU$277 per night from 3 Sept to 4 Sept
AU$277
3 Sept - 4 Sept
includes taxes & fees
With a stay at Quality Inn Ashland - Lake Superior, you'll be centrally located in Ashland, steps from Lake Superior and 15 minutes by foot from Maslowski ...
Quality Inn Ashland - Lake Superior
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.