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

Ashland Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Ashland vacation 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
$169 nightly
The price is $185
Oct 29 - Oct 30
Total with taxes and fees
South Apartment on Main Street
A modern living room with a blue sofa, wooden dining table, and a view of a parking lot through large windows.

2. 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.
$211 nightly
The price is $231
Nov 8 - Nov 9
Total with taxes and fees
North Apartment with Lake Superior Views
A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

3. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (81 reviews)
"A little older cabin than we thought but quaint. Quiet and clean. I would recommend this"
United States
Brian r
$215 nightly
The price is $227
Oct 21 - Oct 22
Total with taxes and fees
Mission Springs Resort
A dining area with a brick fireplace, a painting above it, and a modern kitchen in the background.

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

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
$410 nightly
The price is $459
Oct 19 - Oct 20
Total with taxes and fees
2BR Lake Superior Stay | Hot Tub + Walk Downtown
A brick building with a door and potted plants in front.

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, (4 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.
$432 nightly
The price is $473
Nov 2 - Nov 3
Total with taxes and fees
Historic Main St w/ Lake View | The Flatwater Loft
A gazebo with a snow-covered ground, a bench, and a railing.

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, (264 reviews)
"The jacuzzi tub and the fireplace were the best parts of this condo. The bed is comfortable too (but squeaky—not saying this as a negative, but just mentioning for knowledge lol.) Lisa was accommodating and helpful when necessary. Would stay here again!"
United States
Stephanie
$244 nightly
The price is $273
Oct 19 - Oct 20
Total with taxes and fees
N WI,Bayfield/PEAK fall color now/Stunning/Apostle Is. access/fireplace/jacuzzi
A bedroom with a large window, a bed with a white polka dot bedspread, and a view of a grassy yard and trees.

7. 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.
$216 nightly
The price is $242
Oct 27 - Oct 28
Total with taxes and fees
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A covered porch with a blue railing, a door labeled "Annex 1", and two chairs.

8. 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
$233 nightly
The price is $248
Oct 19 - Oct 20
Total with taxes and fees
Annex No. 1 DePerrys | On Lake Superior Shoreline
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

9. 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, (14 reviews)
"Great place to stay! Plenty of amenities and Dog friendly. Would definitely stay here again. "
United States
Susan B.
$319 nightly
The price is $357
Nov 1 - Nov 2
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
A bedroom with two beds, a dresser, a TV, and a door leading to another room.

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.
$214 nightly
The price is $234
Oct 19 - Oct 20
Total with taxes and fees
Lundy's Black Bear - Lemgrove
A room with a table and chairs, large windows, and a view of a building and water.

11. 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
$203 nightly
The price is $233
Nov 1 - Nov 2
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, Bayfield
A living room with a fireplace, sofas, a TV, and large windows.

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, (22 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
$315 nightly
The price is $359
Oct 20 - Oct 21
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A backyard with a wooden deck, stepping stones, raised garden beds with flowers, and a chair.

13. 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.
$410 nightly
The price is $459
Oct 19 - Oct 20
Total with taxes and fees
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

14. 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.
$240 nightly
The price is $271
Nov 1 - Nov 2
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
A beach with a wooden barrier and calm water reflecting sunlight.

15. 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.
$260 nightly
The price is $274
Nov 1 - Nov 2
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
A cabin with a porch and outdoor seating area, surrounded by a gravel driveway and a wooden fence.

16. 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, (50 reviews)
"The cabin was beautiful and perfect for our stay. Would absolutely stay here again!"
United States
Katie E.
$245 nightly
The price is $258
Nov 10 - Nov 11
Total with taxes and fees
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
A wooden deck with a wicker lounge chair and a table, overlooking a forest.

17. Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (67 reviews)
"Very clean and cozy cabin near Bayfield and Meyers beach"
United States
Reed C.
$351 nightly
The price is $396
Nov 1 - Nov 2
Total with taxes and fees
Woodland Chalet @ Brickyard Creek, Bayfield
A cozy living room with a fireplace, leather sofa, and large windows offering a forest view.

18. Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield
Bayfield
10.0 out of 10, Exceptional, (83 reviews)
"Beautiful place!"
United States
Susan S.
$384 nightly
The price is $433
Nov 1 - Nov 2
Total with taxes and fees
Northwoods Chalet @ Brickyard Creek, Bayfield
A two-story building with a storefront, a visible entrance, and a clear sky.

19. Downtown Bayfield Lodging in Historic Building

Downtown Bayfield Lodging in Historic Building
Bayfield
9.2 out of 10, Wonderful, (5 reviews)
"Loved the rooms! Enjoyed the views of the lake and the quaint downtown area. It was a very quiet and enjoyable stay. I gave it 4 stars only because the sofa was so hard and uncomfortable. We stayed in 2 nights to watch the Brewers play (YAY!) but it was very difficult to get comfortable on the sofa and no amount of throw pillows could change that. That being said, the bed was a dream and the kitchen well appointed. Would I stay there again? Maybe if the sofa was swapped out."
United States
Susan
$396 nightly
The price is $455
Nov 2 - Nov 3
Total with taxes and fees
Downtown Bayfield Lodging in Historic Building
A cozy room with a wooden ceiling, a round mirror, a cushioned sofa, a small table with papers, and a bookshelf.

20. Apostle Pines #4 @ Apostle Highlands Golf Course

Apostle Pines #4 @ Apostle Highlands Golf Course
Bayfield
9.8 out of 10, Exceptional, (21 reviews)
"Awesome place! Views of the golf course was amazing!"
United States
Anonymous traveler
$433 nightly
The price is $489
Nov 1 - Nov 2
Total with taxes and fees
Apostle Pines #4 @ Apostle Highlands Golf Course
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

Lakeside Motel

Lakeside Motel

8/10 Good
"Very friendly and helpful and it was a really nice experience"
Adam 2-night trip
Posted 3 hours ago
Lakeside Motel

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $227 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.