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

Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Ashland vacation rentals

A waterfront promenade with a concrete walkway, metal structures, and calm water.

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
$155 nightly
The price is $169
Nov 10 - Nov 11
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.
$182 nightly
The price is $199
Nov 10 - Nov 11
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, (82 reviews)
"Clean room, great locations"
United States
Van
$209 nightly
The price is $220
Nov 15 - Nov 16
Total with taxes and fees
Mission Springs Resort
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
$373 nightly
The price is $418
Nov 10 - Nov 11
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, (6 reviews)
"We absolutely loved our stay. Everything about the set up (check-in/out, amenities, house logistics) were extremely clear. Communication with the hosts was easy and they were quick to respond when we had a question. The location and decoration of the space was perfect. We all agreed it was the perfect balance of a well-curated space while still feeling really homey!We can’t recommend this place enough and we will definitely be back next time we’re in Ashland!"
United States
Christina N.
$401 nightly
The price is $439
Nov 30 - Dec 1
Total with taxes and fees
Historic Main St w/ Lake View | The Flatwater Loft
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

6. 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)
"Nice house, and nice location."
United States
ben H.
$285 nightly
The price is $319
Nov 29 - Nov 30
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
A cozy living room with a sofa, a coffee table, a fireplace, and a fan.

7. 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, (45 reviews)
"Great location"
United States
vicki A
$372 nightly
The price is $417
Nov 10 - Nov 11
Total with taxes and fees
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A bedroom with a large window, a bed with a white polka dot bedspread, and a view of a grassy yard and trees.

8. 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.
$197 nightly
The price is $221
Nov 10 - Nov 11
Total with taxes and fees
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A bedroom with two beds, a dresser, a TV, and a door leading to another room.

9. 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.
$196 nightly
The price is $215
Nov 10 - Nov 11
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.

10. 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
$197 nightly
The price is $226
Nov 10 - Nov 11
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, Bayfield
A covered porch with a table and chairs, a door, and a window.

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

Cozy 1-bedroom condo located on the lake close to downtown.
La Pointe
$182 nightly
The price is $207
Nov 10 - Nov 11
Total with taxes and fees
Cozy 1-bedroom condo located on the lake close to downtown.
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

12. 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
$236 nightly
The price is $249
Nov 16 - Nov 17
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

13. 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.
$233 nightly
The price is $263
Nov 10 - Nov 11
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
A cabin with a porch and outdoor seating area, surrounded by a gravel driveway and a wooden fence.

14. 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
$212 nightly
The price is $224
Nov 10 - Nov 11
Total with taxes and fees
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
A wooden deck with a glass table and chairs overlooking a lake.

15. Serenity Now | 4BR Trailside / Lakefront Cabin

Serenity Now | 4BR Trailside / Lakefront Cabin
Hurley
10.0 out of 10, Exceptional, (7 reviews)
"Great location and very nice accommodations. Thank you."
United States
Kristin Z.
$277 nightly
The price is $315
Nov 12 - Nov 13
Total with taxes and fees
Serenity Now | 4BR Trailside / Lakefront Cabin
A living room with a fireplace, sofas, a TV, and large windows.

16. 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, (24 reviews)
"Location and the host are incredible!"
United States
Michelle N.
$317 nightly
The price is $361
Nov 11 - Nov 12
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A beach with a wooden barrier and calm water reflecting sunlight.

17. 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.
$229 nightly
The price is $242
Nov 19 - Nov 20
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
A waterfront property with a covered patio, a brick building, and a view of the sea.

18. 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
$369 nightly
The price is $425
Nov 10 - Nov 11
Total with taxes and fees
Downtown Bayfield Lodging in Historic Building
A wooden deck with a wicker lounge chair and a table, overlooking a forest.

19. 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.
$357 nightly
The price is $403
Nov 10 - Nov 11
Total with taxes and fees
Woodland Chalet @ Brickyard Creek, Bayfield
A hotel room with a large bed, a sitting area with a view, and a bathtub.

20. Main @ Hendrickson House

Main @ Hendrickson House
Bayfield
10.0 out of 10, Exceptional, (3 reviews)
"The house was perfect for us. Very clean and had everything we needed to enjoy a relaxing 2 day getaway. I would definitely stay here again!!"
United States
Steven A.
$455 nightly
The price is $523
Nov 10 - Nov 11
Total with taxes and fees
Main @ Hendrickson House
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

The Washburn Inn - On the Lake

The Washburn Inn - On the Lake

10/10 Excellent
"I love staying here! The staff are warm and welcoming, as well as so helpful. The rooms are clean, the location is amazing, and it is a true gem!"
Chloe 3-night trip
Posted 4 days ago
The Washburn Inn - On the Lake

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 $165 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.