Ashland Holiday Rentals

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Our top choices for Ashland holiday rentals

10.0 out of 10, Exceptional, (42)
"We loved our stay! It was a beautiful place and so comfortable."
United States
Jennifer S.
The price is NZ$336
includes taxes & fees
29 Dec - 30 Dec
North Apartment with Lake Superior Views

Holiday Home in Ashland

A Cozy Getaway in Ashland
10.0 out of 10, Exceptional, (14)
"Great place and host"
United States
Dustin W.
The price is NZ$412
includes taxes & fees
7 Jan - 8 Jan 2026
A Cozy Getaway in Ashland
9.8 out of 10, Exceptional, (229)
"Location was perfect!"
United States
amy g.
The price is NZ$316
includes taxes & fees
28 Dec - 29 Dec
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
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$408
includes taxes & fees
18 Jan - 19 Jan 2026
The Copper Squirrel is a secluded full log cabin on 10 acres.
10.0 out of 10, Exceptional, (1)
"A large group of us rented the Davos Chalet for a long weekend. There was more than enough room for us all. The common area was great for us to eat meals and hang out. The kids loved the game room in the basement. "
United States
Stacy H.
The price is NZ$2,966
includes taxes & fees
28 Dec - 29 Dec
Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
9.6 out of 10, Exceptional, (35)
"Clean, well organized cabin, great Decor!"
United States
kathy m.
The price is NZ$385
includes taxes & fees
4 Jan - 5 Jan 2026
Brookside Hide-A-Way #2, Port Superior, Bayfield
10.0 out of 10, Exceptional, (76)
"It was perfect. Clean, cozy. Great get away for the wife and me "
United States
Bill R.
The price is NZ$674
includes taxes & fees
7 Jan - 8 Jan 2026
Northwoods Chalet @ Brickyard Creek, Bayfield
9.8 out of 10, Exceptional, (16)
"Very clean home in a private area! We did a lot of UTV riding and thus property was centrally located to me all of our needs. "
United States
Janet K.
The price is NZ$257
includes taxes & fees
12 Jan - 13 Jan 2026
Modern Cabin on a River Bluff
2.0 star property
The price is NZ$326
includes taxes & fees
4 Jan - 5 Jan 2026
Lundy's Black Bear - Lemgrove
10.0 out of 10, Exceptional, (17)
"Super clean, super comfortable, perfect peaceful location."
United States
Chris C.
The price is NZ$442
includes taxes & fees
29 Dec - 30 Dec
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
9.8 out of 10, Exceptional, (58)
"Exceeded expectations! The best of both worlds. Rustic, but with all of the amenities you could want. Perfectly private and secluded yet very close to Bayfield. Clean, fresh, and breezy. We loved the fully equipped kitchen, and the screened-in deck. There was no need to eat out. Online check in was easy, and we were able to get help via text when we needed extra towels and when we had a question about the TV. "
United States
Wendy L.
The price is NZ$655
includes taxes & fees
6 Jan - 7 Jan 2026
Woodland Chalet @ Brickyard Creek, Bayfield
10.0 out of 10, Exceptional, (52)
"The cabin is extremely clean and well organized with anything you can think of. It's located really close to town, but just outside, so you have peace and quiet. The hosts are very responsive and it made for a perfect trip. "
United States
Matthew
The price is NZ$548
includes taxes & fees
30 Dec - 31 Dec
Bayfield Fruit Loop Retreat - Main Cottage
9.2 out of 10, Wonderful, (100)
"Great location and exactly what we needed for our two night stay in Bayfield. Everything in town was walkable from the VRBO as well. Would stay again!"
United States
Alexander L.
The price is NZ$394
includes taxes & fees
26 Dec - 27 Dec
Lake Side Room at The Copper Trout.
10.0 out of 10, Exceptional, (1)
The price is NZ$554
includes taxes & fees
4 Jan - 5 Jan 2026
Up North Oasis - Families & Dogs in the Bayfield Area
9.6 out of 10, Exceptional, (15)
"Very clean, relaxing and beautiful location! "
United States
Garry H.
The price is NZ$811
includes taxes & fees
6 Jan - 7 Jan 2026
Apostle Pines #4 @ Apostle Highlands Golf Course
9.0 out of 10, Wonderful, (11)
"This is a nice home nestled in a beautiful wooded area. Very clean and comfortable, nice attention to detail. It’s in close proximity to Bayfield, which is a hidden gem of the Great Lakes area. We’ve been to 49 states, and this area is one of our favorites."
United States
Matt
The price is NZ$784
includes taxes & fees
26 Dec - 27 Dec
Carriage House - Chequamegon Bay, Bayfield
2.0 star property
The price is NZ$326
includes taxes & fees
5 Jan - 6 Jan 2026
Lundy's Black Bear - Rosewood
9.8 out of 10, Exceptional, (8)
"The home looks as pictured and is settled up on a hill with great sight lines over the town and Lake Superior. My daughter and I didn’t mind the extra muscle burn walking up/down hill to walk the shops or grab a bit to eat. The location was an easy drive to park if desired downtown or head to Washburn for dinner. The room had all necessities for the kitchen, bathroom, shower, and cozy bed after kayaking and hiking. Thanks for a great stay! "
United States
Erin W.
The price is NZ$565
includes taxes & fees
26 Dec - 27 Dec
Outer Island Apartment @ The Copper Crown
2.0 star property
The price is NZ$369
includes taxes & fees
6 Jan - 7 Jan 2026
Lundy's Black Bear - Blair Oaks
10.0 out of 10, Exceptional, (111)
"Beautiful views, great location and proximity to Bayfield. Loved our stay. Will be back in the fall! "
United States
Monica O.
The price is NZ$1,316
includes taxes & fees
31 Dec - 1 Jan 2026
Lake Shore Home with private dock and large deck--1 mile from Bayfield
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 Hotel Reviews

Find out more about Ashland

Everything you need to know about Ashland 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 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. 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 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 holiday rentals we have selected for you start as low as NZ$304 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to Ashland Mural Walk, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the scenic lakeside in Ashland. Make sure you have time to check out the architecture and waterfront during your trip.

What are some of the best holiday rentals that Ashland has to offer?

Downtown Bayfield Home W/ Lake Views, Steps to Ferry & Marina: This holiday home rental outside of Ashland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Ashland?

With 9 Expedia holiday rentals, you're guaranteed to find just the right place for your Ashland stay.

What’s there to see and do in Ashland?

Chequamegon Bay and Lake Superior are a couple of scenic spots to enjoy the outdoors, whereas Ashland Historical Museum is one of the cultural attractions. While here, Ashland Mural Walk and Northern Great Lakes Visitor Center are other places worth a visit.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.