Photo by Anthony Ball

Ashland County Holiday Rentals

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Our top choices for Ashland County holiday rentals

10.0 out of 10, Exceptional, (17)
"Super clean, super comfortable, perfect peaceful location."
United States
Chris C.
The price is NZ$449
includes taxes & fees
18 Dec - 19 Dec
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
10.0 out of 10, Exceptional, (4)
"Great location, clean, owners were responsive and helped with any issues. I would stay here again. "
United States
Angela M.
Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach
9.6 out of 10, Exceptional, (222)
"Very clean perfect size for 2people,,easy access to Bayfield!"
United States
Gayle J.
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles
3.5 star property
9.0 out of 10, Wonderful, (316)
"Colors of the trees were beautiful, staff helpful, trails plentiful and walkable."
United States
Kenneth
The price is NZ$539
includes taxes & fees
18 Dec - 19 Dec
Telemark Northwoods Lodging
9.4 out of 10, Exceptional, (164)
"Great accommodations. "
United States
Alison L.
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles

Cottage in Ashland

Mission Springs Resort
3.0 star property
9.4 out of 10, Exceptional, (67)
"The accomodations were lovely and quaint! Everything was clean and comfy."
United States
Cynthia
Mission Springs Resort
10.0 out of 10, Exceptional, (103)
"Lovely home, spotless, perfect location, well-stocked kitchen, close to Hayward and golf, What’s not to love for a family vacation? "
United States
Linda J.
Executive Custom Log Lodge on Little Round Lake
9.8 out of 10, Exceptional, (50)
"Loved it, great location would go back!Thanks."
United States
Michelle N H.
Cozy Cabin on Secluded Peninsula
9.6 out of 10, Exceptional, (214)
"This place is soul-restoring!"
United States
Michael R.
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
10.0 out of 10, Exceptional, (3)
"Dave was an amazing host, he had the property setup for us. Had a ton of little xtras and everything labeled and easy to understand and use. "
United States
Jeff H.
Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.
10.0 out of 10, Exceptional, (6)
"This house is a great place to stay. We highly recommend!"
United States
Kristy W.
Downtown Bayfield Home W/ Lake Views, Steps to Ferry & Marina
10.0 out of 10, Exceptional, (25)
"We had a wonderful stay and enjoyed swimming, relaxing, and making family memories. The home was well appointed - lots of towels, kitchen essentials, etc. we hope to visit again soon!"
United States
Steve C.
Lakefront Cabin w/ Pool Table+Waterfall: Northwoods Nostalgia + Modern Amenities
10.0 out of 10, Exceptional, (27)
"Perfect little cabin. So easy to kick back and relax and with local attractions being just 15-20 min away the location was perfect. Clean cabin, very responsive and kind host. Would 100% recommend to anyone looking to explore the beautiful Bayfield area."
United States
Lance K.
The price is NZ$472
includes taxes & fees
11 Jan - 12 Jan 2026
The Copper Squirrel is a secluded full log cabin on 10 acres.
9.8 out of 10, Exceptional, (18)
"The house was perfect for a weekend get away up north!"
United States
Bobbi B.
The price is NZ$1,833
includes taxes & fees
18 Dec - 19 Dec
Dual Cabins Avail Christmas-Hot Tub, 2 Kitchens
9.8 out of 10, Exceptional, (229)
"Location was perfect!"
United States
amy g.
The price is NZ$259
includes taxes & fees
22 Dec - 23 Dec
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
9.4 out of 10, Exceptional, (12)
"Over all it was a very nice stay the lake was a little over run with weeds but we enjoyed none the less!"
United States
Allan J.
Grand View Lodge -New Listing With Room For The Family

Cabin in Hayward

Moose Lake Hayward WI
2.0 star property
10.0 out of 10, Exceptional, (11)
"Our first time staying here. Perfect cabin for our weekend of fishing. Wish we had booked a couple more days. Walleye fishing was excellent. We will be back."
United States
Tony S
Moose Lake Hayward WI
9.6 out of 10, Exceptional, (258)
"Enjoyed our stay."
United States
Colleen
Bayfield- Charming Condo, Jumping Off Point to Apostles
10.0 out of 10, Exceptional, (7)
"The house was perfect for our stay! Very comfortable and easy access. The kitchen and laundry room come with lots of amenities likes clean pots, pans, bowls, coffee maker etc and laundry detergent. Check in was super easy. Door passcode was sent via email a day ahead of actual checkin and wifi password was posted on the fridge. We would definitely book this place again. "
United States
Blia X.
Big Chip - 1 is in the heart of the Chippewa Flowage 20 minutes from Hayward, WI
9.8 out of 10, Exceptional, (29)
"Wonderful accommodations. Great spot for a quick getaway!"
United States
Joe B.
The price is NZ$467
includes taxes & fees
18 Dec - 19 Dec
Motorsports Basecamp near lakes and forest
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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Top Ashland County Hotel Reviews

Find out more about Ashland County

Everything you need to know about Ashland County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashland County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland County holiday rentals we have selected for you start as low as NZ$259 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland County rentals

At Expedia, we put the best Ashland County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ashland County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.