A cluster of mushrooms growing on a moss-covered log in a forest.

Ashland County Holiday Rentals

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Our top choices for Ashland County holiday rentals

A modern kitchen with a wooden table and bar stools, a ceiling fan, and pendant lights.

1. South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (25 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is NZ$312
includes taxes & fees
15 Nov - 16 Nov
South Apartment on Main Street
A covered porch with a table and chairs, a door, and a window.

2. Cozy 1-bedroom condo located on the lake close to downtown.

Cozy 1-bedroom condo located on the lake close to downtown.
La Pointe
The price is NZ$377
includes taxes & fees
12 Nov - 13 Nov
Cozy 1-bedroom condo located on the lake close to downtown.
A cabin with a porch and outdoor seating area, surrounded by a gravel driveway and a wooden fence.

3. Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4

Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
Mellen
10.0 out of 10, Exceptional, (55 reviews)
"Everything was amazing! Will be back"
United States
Kimberly
The price is NZ$429
includes taxes & fees
30 Nov - 1 Dec
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
A modern kitchen with a central island, wooden stools, a stainless steel refrigerator, and a ceiling fan.

4. 2BR Lake Superior Stay | Hot Tub + Walk Downtown

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
The price is NZ$746
includes taxes & fees
12 Nov - 13 Nov
2BR Lake Superior Stay | Hot Tub + Walk Downtown
A rustic log cabin with a green roof, a small porch, and a view of a lake.

5. Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.

Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
Butternut
10.0 out of 10, Exceptional, (82 reviews)
"Cute and cozy winter rental. Looks like it would be a great summer spot too!"
United States
David M.
The price is NZ$565
includes taxes & fees
12 Nov - 13 Nov
Blissful cozy, year round, lakeside cabin on Butternut Lake. Dogs welcome.
A living room with a wooden floor, a television mounted on the wall, a desk with a chair, a sofa, and a lamp.

6. Cozy home in Wisconsin's recreational northwoods.

Cozy home in Wisconsin's recreational northwoods.
Butternut
7.6 out of 10, Good, (5 reviews)
"Weather was hot, fishing was difficult at best, we had a good time."
United States
Robert
The price is NZ$378
includes taxes & fees
12 Nov - 13 Nov
Cozy home in Wisconsin's recreational northwoods.
A deer standing on a road with dense green foliage on both sides.

7. Rustic campground in Butternut

Rustic campground in Butternut
Butternut
The price is NZ$107
includes taxes & fees
12 Nov - 13 Nov
Rustic campground in Butternut
A wooden deck with two wicker chairs and a table, overlooking a forest with autumn foliage.

8. Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (331 reviews)
"Clean, quiet…easy check in. Great communication pre check-in. Beautiful setting/area. Will be back…"
United States
Thomas
The price is NZ$175
includes taxes & fees
12 Nov - 13 Nov
Telemark Northwoods Lodging
A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

9. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (82 reviews)
"Clean room, great locations"
United States
Van
The price is NZ$382
includes taxes & fees
15 Nov - 16 Nov
Mission Springs Resort
A flat-screen TV on a wooden TV stand in a living room with a patterned rug.

10. Cozy Home in Ironwood, MI

Cozy Home in Ironwood, MI
Ironwood
9.8 out of 10, Exceptional, (94 reviews)
"Bed was nice"
United States
Sarah
The price is NZ$353
includes taxes & fees
19 Nov - 20 Nov
Cozy Home in Ironwood, MI
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

11. The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!

The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Bayfield
10.0 out of 10, Exceptional, (45 reviews)
"Enjoyed our few nights at this lovely home. So many special touches! Really enjoyed the screened in area and lighting fires and having smores around the fire pit."
United States
elizabeth
The price is NZ$451
includes taxes & fees
16 Nov - 17 Nov
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A bedroom with two beds, a dresser, a TV, and a door leading to another room.

12. Lundy's Black Bear - Lemgrove

Lundy's Black Bear - Lemgrove
Drummond
9.0 out of 10, Wonderful, (4 reviews)
"Newly constructed with only 3 units so very quiet."
United States
Cheryl A.
The price is NZ$393
includes taxes & fees
12 Nov - 13 Nov
Lundy's Black Bear - Lemgrove
A bedroom with a large window, a bed with a white polka dot bedspread, and a view of a grassy yard and trees.

13. PORT 1 bedroom studio with AC just 2.5 miles from Bayfield

PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
Bayfield
10.0 out of 10, Exceptional, (1 review)
"Great location, nice view from bedroom. Easy in and out and good communication. Could use darker shades."
United States
scott d.
The price is NZ$404
includes taxes & fees
12 Nov - 13 Nov
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A beach with a wooden barrier and calm water reflecting sunlight.

14. The Copper Squirrel is a secluded full log cabin on 10 acres.

The Copper Squirrel is a secluded full log cabin on 10 acres.
Bayfield
10.0 out of 10, Exceptional, (47 reviews)
"Great place to relax and close enough to Bayfield, a fun and charming seaport."
United States
Tad S.
The price is NZ$433
includes taxes & fees
19 Nov - 20 Nov
The Copper Squirrel is a secluded full log cabin on 10 acres.
A living room with a sectional sofa, a coffee table, a floor lamp, and a window with blinds.

15. Hurley: location for all hobbies, holidays, events

Hurley: location for all hobbies, holidays, events
Hurley
9.4 out of 10, Exceptional, (38 reviews)
"Great location, great host will stay again"
United States
Brian B.
The price is NZ$343
includes taxes & fees
12 Nov - 13 Nov
Hurley: location for all hobbies, holidays, events
A weathered driftwood piece on a sandy beach with waves crashing in the background.

16. Cozy Corner Home Dogs Welcome

Cozy Corner Home Dogs Welcome
Ironwood
9.8 out of 10, Exceptional, (24 reviews)
"It was perfect for our group."
United States
Todd G.
The price is NZ$572
includes taxes & fees
16 Nov - 17 Nov
Cozy Corner Home Dogs Welcome
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

17. Brookside Hide-A-Way #2, Port Superior, Bayfield

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (42 reviews)
"Great place and wonderful rear deck. Wish we had more time to spend there."
United States
Don L.
The price is NZ$471
includes taxes & fees
12 Nov - 13 Nov
Brookside Hide-A-Way #2, Port Superior, Bayfield
A spacious living room with a high ceiling, skylights, a sofa, a coffee table, and a chair.

18. New, Remodeled, Luxury Loft w/Hot Tub & Rooftop Patio

New, Remodeled, Luxury Loft w/Hot Tub & Rooftop Patio
Ironwood
10.0 out of 10, Exceptional, (74 reviews)
"Wonderful place! Can’t wait to come back!"
United States
Michael
The price is NZ$520
includes taxes & fees
12 Nov - 13 Nov
New, Remodeled, Luxury Loft w/Hot Tub & Rooftop Patio
A room with a table and chairs, large windows, and a view of a building and water.

19. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (26 reviews)
"Nice and cozy with a great view. The outside spaces could use some tidying up and paint, but once inside the place was awesome."
United States
Lori
The price is NZ$414
includes taxes & fees
12 Nov - 13 Nov
Lower Flat @ Steeple Hill Flats, Bayfield
A wooden-paneled room with a flat-screen TV mounted on the wall, a small table with a lamp, a cushioned chair, and a sofa.

20. Vintage home located in Ironwood Michigan

Vintage home located in Ironwood Michigan
Ironwood
8.4 out of 10, Very good, (36 reviews)
"The host was very communicative, which made our stay great. The house was clean and was exactly what we needed for our visit to the UP. "
United States
Lauren B.
The price is NZ$367
includes taxes & fees
12 Nov - 13 Nov
Vintage home located in Ironwood Michigan
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

Hotel Chequamegon, BW Signature Collection

Hotel Chequamegon, BW Signature Collection

10/10 Excellent
"It was expensive for a hotel where I’m from"
Diane 1-night trip
Posted 12 hours ago
Hotel Chequamegon, BW Signature Collection

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$175 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.