Holiday Homes in Ashland

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Ashland

Lake Shore Home with private dock and large deck--1 mile from Bayfield

10.0 out of 10, Exceptional, (108)
"The home and location were perfect for our friends weekend! Views of Lake Superior are seen from every room. We enjoyed the comfortable beds and appreciated the host’s attention to detail. Monica was very easy to communicate with and would love to return for another stay!"
The price is AU$935
includes taxes & fees
27 Oct - 28 Oct
Lake Shore Home with private dock and large deck--1 mile from Bayfield

SUMMER SPECIALS Beautiful lake front, beach and pool table

9.8 out of 10, Exceptional, (17)
"We had a great stay. Lots of room, beautiful views, a very clean updated home"
SUMMER SPECIALS Beautiful lake front, beach and pool table

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

10.0 out of 10, Exceptional, (109)
"Couldn't be happier with the home and the hosts."
Newly remodeled lake home ! Steps away from the beautiful pike lake chain

Harbor Hill House Bayfield, WI

2.0 star property
9.0 out of 10, Wonderful, (2)
"The view was awesome!"
Harbor Hill House Bayfield, WI

Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

10.0 out of 10, Exceptional, (54)
"Had a great weekend stay, the house was very clean and well kept. The owners have done an excellent job fixing it up. The owners do a great job with communication as well. I'd highly recommend staying here. "
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!

9.8 out of 10, Exceptional, (79)
"We loved our stay at Lori and Craig’s home in the woods. The house is wonderful and felt like a home from the moment we entered. There was plenty of space for the five of us. The house was sparkling clean and had everything we needed. The beds were super comfortable, the towels plush and cozy. We loved watching and listening to birds on the screened-in porch and eating breakfast and playing games on the big table. Unfortunately, our stay was short but we are hoping to return one day….."
4 Bed 2 Bath Escape in the Woods. 10 minutes to the beach!

Entire Home Near Lake Superior

10.0 out of 10, Exceptional, (29)
"Great time thanks!!!"
Entire Home Near Lake Superior

Near Hurley, On the Trail, Large Parking Area, Dog Friendly -The Cary Mine House

9.8 out of 10, Exceptional, (27)
"Great place, great location!"
Near Hurley, On the Trail, Large Parking Area, Dog Friendly -The Cary Mine House

Private Beach and Endless Water

8.8 out of 10, Excellent, (45)
"Very little traffic and very quiet beach. It was early in the year before tourist season but very quiet neighborhood. Would definitely stay here again. House was very clean. "
Private Beach and Endless Water

Luxurious Lake Superior Estate with Outdoor Hot Tub

10.0 out of 10, Exceptional, (55)
"Our group had 2 families; 4 adults and 5 kids. We all had a wonderful time. Lots of space both indoors and out. The kiddos loved the bunk room. Beautiful view of the lake and easy access to Bayfield. We hope to return someday. "
Luxurious Lake Superior Estate with Outdoor Hot Tub

Spacious 5-bedroom house in serene Clam Lake with WiFi

9.0 out of 10, Wonderful, (2)
"Easy to find - family friendly! Loved our stay! "
Spacious 5-bedroom house in serene Clam Lake with WiFi

Spacious, secluded sanctuary! Very clean! 5 Queen Beds! Wildlife viewing.

9.8 out of 10, Exceptional, (26)
"The house was great and the area is amazing. Very quiet and peaceful with tons of wildlife. Saw so many deer - definitely keep your eyes open and follow the posted speed limit!"
Spacious, secluded sanctuary! Very clean! 5 Queen Beds! Wildlife viewing.

Lake Superior Log Home, Northern Wisconsin

10.0 out of 10, Exceptional, (50)
"Great place to stay. Location was amazing"
Lake Superior Log Home, Northern Wisconsin

Ride your ATVs and snowmobiles directly from the house!

10.0 out of 10, Exceptional, (38)
"Had an amazing time at this wonderful location. Such a gem of a place to stay. Loved it"
Ride your ATVs and snowmobiles directly from the house!

Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse

9.0 out of 10, Wonderful, (8)
"We enjoyed every minute of our stay in this comfortable, well-appointed and spotlessly clean house. Highly recommend!"
The price is AU$626
includes taxes & fees
3 Oct - 4 Oct
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse

Cozy House (Hurley, WI/Ironwood, MI area)

9.4 out of 10, Exceptional, (40)
"Nice place"
Cozy House (Hurley, WI/Ironwood, MI area)

Tiny’s Retirement Home near the trails

10.0 out of 10, Exceptional, (41)
"Clean, modern and well-appointed place to stay. A comfortable repeat place for a family stay."
Tiny’s Retirement Home near the trails

Spacious home with EV charging station two miles from Big Bay Town Park.

10.0 out of 10, Exceptional, (6)
"We had a great time staying at the property! Great amenities and lots of character. Super responsive host when we had trouble checking in!"
Spacious home with EV charging station two miles from Big Bay Town Park.

Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

9.8 out of 10, Exceptional, (7)
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.

10.0 out of 10, Exceptional, (53)
"The owners of this Airbnb thought of everything for our stay in Bayfield. This is nicely appointed and it had everything we could possibly need or want. Right down to a gift certificate to the local coffee shop and homemade dog biscuits for our pup. It’s located just a short five minutes from downtown Bayfield in a really nice quiet location. Loved every moment of our stay!"
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Find out more about Ashland

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
779
Accommodation
187 Holiday Homes
Lowest Price
AU$626
Highest Price
AU$935

Explore a world of travel with Expedia