A sandy beach with a wooden structure extending into the water.

Ashland Holiday Rentals

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Our top choices for Ashland holiday rentals

1. South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (24 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is NZ$383
includes taxes & fees
30 Sept - 1 Oct
South Apartment on Main Street

2. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (79 reviews)
"A little older cabin than we thought but quaint. Quiet and clean. I would recommend this"
United States
Brian r
The price is NZ$267
includes taxes & fees
27 Oct - 28 Oct
Mission Springs Resort

3. North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (46 reviews)
"Great location, clean and comfortable. "
United States
Heather Ann M.
The price is NZ$474
includes taxes & fees
27 Oct - 28 Oct
North Apartment with Lake Superior Views

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

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
The price is NZ$893
includes taxes & fees
8 Oct - 9 Oct
2BR Lake Superior Stay | Hot Tub + Walk Downtown

5. Lake Superior Stay - Fire Pit Patio - Pet Friendly

Lake Superior Stay - Fire Pit Patio - Pet Friendly
Ashland
9.8 out of 10, Exceptional, (9 reviews)
"Cute place "
United States
Donald B.
The price is NZ$866
includes taxes & fees
5 Oct - 6 Oct
Lake Superior Stay - Fire Pit Patio - Pet Friendly

6. Historic Main St w/ Lake View | The Flatwater Loft

Historic Main St w/ Lake View | The Flatwater Loft
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"Awesome location, great communication with host,Flat was newly decorated in 40’s deco. Loved loved the charm of the flat."
United States
Judy D.
The price is NZ$876
includes taxes & fees
19 Oct - 20 Oct
Historic Main St w/ Lake View | The Flatwater Loft

7. Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Bayfield
9.8 out of 10, Exceptional, (261 reviews)
"Wonderful clean and well appointed place!"
United States
Kinda S.
The price is NZ$383
includes taxes & fees
7 Oct - 8 Oct
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

8. All season cottage overlooking the private beach on Lake Superior

All season cottage overlooking the private beach on Lake Superior
Washburn
10.0 out of 10, Exceptional, (21 reviews)
"Clean, quiet, beautiful private beach! "
United States
Abby K.
The price is NZ$1,084
includes taxes & fees
3 Oct - 4 Oct
All season cottage overlooking the private beach on Lake Superior

9. Cozy 1-bedroom studio in serene Bayfield with AC

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
9.2 out of 10, Wonderful, (7 reviews)
The price is NZ$522
includes taxes & fees
7 Oct - 8 Oct
Cozy 1-bedroom studio in serene Bayfield with AC

10. Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks
Drummond
10.0 out of 10, Exceptional, (5 reviews)
"😀"
United States
Lynne
The price is NZ$404
includes taxes & fees
27 Oct - 28 Oct
Lundy's Black Bear - Blair Oaks

11. Up North Oasis - Families & Dogs in the Bayfield Area

Up North Oasis - Families & Dogs in the Bayfield Area
Washburn
10.0 out of 10, Exceptional, (11 reviews)
"We had a lovely stay and the accommodations were just what we needed. We are planning to stay here again. "
United States
Joan Q.
The price is NZ$664
includes taxes & fees
21 Oct - 22 Oct
Up North Oasis - Families & Dogs in the Bayfield Area

12. Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
Bayfield
10.0 out of 10, Exceptional, (20 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
The price is NZ$632
includes taxes & fees
29 Oct - 30 Oct
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

13. Annex No. 1 DePerrys | On Lake Superior Shoreline

Annex No. 1 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (48 reviews)
"Cute and cozy little place! Perfect for our anniversary weekend getaway!"
United States
Kabao
The price is NZ$430
includes taxes & fees
25 Oct - 26 Oct
Annex No. 1 DePerrys | On Lake Superior Shoreline

14. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Washburn
9.0 out of 10, Wonderful, (41 reviews)
"We had a great time! Beautiful home with easy access to all the South Shore has to offer. "
United States
Anastasia Hopkins F.
The price is NZ$809
includes taxes & fees
4 Oct - 5 Oct
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

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

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (41 reviews)
"Great place and wonderful rear deck. Wish we had more time to spend there."
United States
Don L.
The price is NZ$495
includes taxes & fees
29 Oct - 30 Oct
Brookside Hide-A-Way #2, Port Superior, Bayfield

16. Suite One at La Pointe Lodging

Suite One at La Pointe Lodging
La Pointe
9.8 out of 10, Exceptional, (28 reviews)
"Lovely place!!"
United States
Anne R.
The price is NZ$540
includes taxes & fees
8 Oct - 9 Oct
Suite One at La Pointe Lodging

17. Lake Side Room at The Copper Trout.

Lake Side Room at The Copper Trout.
Bayfield
9.2 out of 10, Wonderful, (113 reviews)
"Room was clean and in a great location for enjoying the greater Bayfield area."
United States
Sally R.
The price is NZ$511
includes taxes & fees
30 Sept - 1 Oct
Lake Side Room at The Copper Trout.

18. 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, (46 reviews)
"The cabin was beautiful and perfect for our stay. Would absolutely stay here again!"
United States
Katie E.
The price is NZ$432
includes taxes & fees
26 Oct - 27 Oct
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4

19. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (25 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$441
includes taxes & fees
29 Oct - 30 Oct
Lower Flat @ Steeple Hill Flats, Bayfield

20. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (69 reviews)
"Great central location in downtown Bayfield. Very clean. Perfect for our family of four’s long weekend in Bayfield."
United States
Andrew
The price is NZ$648
includes taxes & fees
30 Sept - 1 Oct
The Little Bodin
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ashland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ashland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Ashland. Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Ashland short-term rentals, that won’t be hard to do.

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?

ENTIRE LAKEFRONT 10-bedroom Chateau Getaway at Whitecap Mountains Resort: This holiday home rental outside of Ashland is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Ashland?

With 13 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, Chequamegon Bay Golf Course 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.