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

Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

1. 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 CA $223
CA $235 total
includes taxes & fees
Oct 21 - Oct 22
Mission Springs Resort

2. 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 CA $141
CA $264 total
includes taxes & fees
Nov 9 - Nov 10
South Apartment on Main Street

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 CA $192
CA $348 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $271
CA $672 total
includes taxes & fees
Nov 1 - Nov 2
2BR Lake Superior Stay | Hot Tub + Walk Downtown

5. 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, (3 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 CA $503
CA $807 total
includes taxes & fees
Oct 28 - Oct 29
Historic Main St w/ Lake View | The Flatwater Loft

6. N WI,Bayfield/PEAK fall color now/Stunning/Apostle Is. access/fireplace/jacuzzi

N WI,Bayfield/PEAK fall color now/Stunning/Apostle Is. access/fireplace/jacuzzi
Bayfield
9.8 out of 10, Exceptional, (262 reviews)
"Wonderful place to stay. Lisa is so responsive and truly wants to make sure your needs are met."
United States
Karen W.
N WI,Bayfield/PEAK fall color now/Stunning/Apostle Is. access/fireplace/jacuzzi

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

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
9.4 out of 10, Exceptional, (8 reviews)
Cozy 1-bedroom studio in serene Bayfield with AC

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

Up North Oasis - Families & Dogs in the Bayfield Area
Washburn
9.8 out of 10, Exceptional, (12 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 CA $221
CA $509 total
includes taxes & fees
Nov 1 - Nov 2
Up North Oasis - Families & Dogs in the Bayfield Area

9. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Washburn
8.8 out of 10, Excellent, (43 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 CA $298
CA $653 total
includes taxes & fees
Oct 11 - Oct 12
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

10. 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 CA $163
CA $334 total
includes taxes & fees
Oct 11 - Oct 12
Lundy's Black Bear - Lemgrove

11. 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 CA $189
CA $329 total
includes taxes & fees
Nov 1 - Nov 2
Brookside Hide-A-Way #2, Port Superior, Bayfield

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, (21 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
The price is CA $213
CA $511 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $221
CA $357 total
includes taxes & fees
Oct 19 - Oct 20
Annex No. 1 DePerrys | On Lake Superior Shoreline

14. 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.
Suite One at La Pointe Lodging

15. 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 CA $196
CA $325 total
includes taxes & fees
Nov 9 - Nov 10
Lower Flat @ Steeple Hill Flats, Bayfield

16. Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (93 reviews)
"The room was awesome - all that we needed. Right in town so very walkable. We would definitely stay here again when we are in the area."
United States
Brendon
The price is CA $355
CA $458 total
includes taxes & fees
Nov 1 - Nov 2
Avenue Side Room at The Copper Trout.

17. 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, (48 reviews)
"The cabin was beautiful and perfect for our stay. Would absolutely stay here again!"
United States
Katie E.
The price is CA $284
CA $339 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4

18. Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (67 reviews)
"Host was great and very responsive to questions about check in and once we arrived."
United States
Alex D.
The price is CA $295
CA $565 total
includes taxes & fees
Nov 1 - Nov 2
Woodland Chalet @ Brickyard Creek, Bayfield

19. 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, (45 reviews)
"Great place to relax and close enough to Bayfield, a fun and charming seaport."
United States
Tad S.
The price is CA $269
CA $391 total
includes taxes & fees
Nov 1 - Nov 2
The Copper Squirrel is a secluded full log cabin on 10 acres.

20. Outer Island Apartment @ The Copper Crown

Outer Island Apartment @ The Copper Crown
Bayfield
9.8 out of 10, Exceptional, (15 reviews)
"Great location and nice little space to stay near the downtown area."
United States
Rickandheather H.
The price is CA $327
CA $542 total
includes taxes & fees
Oct 12 - Oct 13
Outer Island Apartment @ The Copper Crown
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Ashland?

Yes, there are vacation rentals in Ashland close to Ashland Mural Walk, or you can select a more secluded option if you want 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's the top vacation rental that Ashland has to offer?

ENTIRE LAKEFRONT 10-bedroom Chateau Getaway at Whitecap Mountains Resort: This vacation home rental outside of Ashland is located on a lake and has an indoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Ashland?

With 13 Expedia vacation rentals, you're sure 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 vacation rentals like in Ashland?

Vacation rentals are private properties you can stay in for several days or longer in Ashland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for families.