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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (24 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
$195 nightly
The price is $215
Sep 30 - Oct 1
Total with taxes and fees
South Apartment on Main Street
A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

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
$140 nightly
The price is $147
Oct 29 - Oct 30
Total with taxes and fees
Mission Springs Resort
A modern living room with a blue sofa, wooden dining table, and a view of a parking lot through large windows.

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.
$240 nightly
The price is $264
Oct 8 - Oct 9
Total with taxes and fees
North Apartment with Lake Superior Views
A dining area with a wooden table and chairs, a hanging light fixture, a fireplace, and a painting on the wall.

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

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
$386 nightly
The price is $432
Oct 27 - Oct 28
Total with taxes and fees
2BR Lake Superior Stay | Hot Tub + Walk Downtown
A living room with a blue accent wall, a round mirror, a white sofa with blue cushions, a brown leather ottoman, and a white shelving unit with decorative items.

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.
$419 nightly
The price is $469
Oct 28 - Oct 29
Total with taxes and fees
Lake Superior Stay - Fire Pit Patio - Pet Friendly
A brick building with a door and potted plants in front.

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.
$437 nightly
The price is $479
Oct 18 - Oct 19
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.

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.
$191 nightly
The price is $214
Oct 4 - Oct 5
Total with taxes and fees
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
A wooden deck with a view of the ocean and a full moon.

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.
$352 nightly
The price is $394
Oct 14 - Oct 15
Total with taxes and fees
All season cottage overlooking the private beach on Lake Superior
A dining area with a table, chairs, and a large window with a view of a green landscape.

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)
$255 nightly
The price is $286
Sep 29 - Sep 30
Total with taxes and fees
Cozy 1-bedroom studio in serene Bayfield with AC
A bedroom with two beds, a wooden dresser, a TV mounted on the wall, and a red door.

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
$209 nightly
The price is $229
Sep 29 - Sep 30
Total with taxes and fees
Lundy's Black Bear - Blair Oaks
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

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.
$321 nightly
The price is $360
Oct 5 - Oct 6
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
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, (20 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
$295 nightly
The price is $336
Sep 30 - Oct 1
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A covered porch with a blue railing, a door labeled "Annex 1", and two chairs.

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
$225 nightly
The price is $240
Oct 6 - Oct 7
Total with taxes and fees
Annex No. 1 DePerrys | On Lake Superior Shoreline
A backyard with a wooden deck, stepping stones, raised garden beds with flowers, and a chair.

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.
$388 nightly
The price is $435
Oct 4 - Oct 5
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.

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.
$243 nightly
The price is $274
Oct 7 - Oct 8
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
A deck with two Adirondack chairs, a door, and a window.

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.
$263 nightly
The price is $294
Oct 8 - Oct 9
Total with taxes and fees
Suite One at La Pointe Lodging
A bedroom with a bed, a bedside table, a lamp, and a window with blinds.

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.
$244 nightly
The price is $278
Sep 30 - Oct 1
Total with taxes and fees
Lake Side Room at The Copper Trout.
A cabin with a porch and outdoor seating area, surrounded by a gravel driveway and a wooden fence.

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.
$220 nightly
The price is $232
Sep 29 - Sep 30
Total with taxes and fees
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
A room with a table and chairs, large windows, and a view of a building and water.

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
$215 nightly
The price is $247
Oct 18 - Oct 19
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, Bayfield

20. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (68 reviews)
"Great central location in downtown Bayfield. Very clean. Perfect for our family of four’s long weekend in Bayfield."
United States
Andrew
$311 nightly
The price is $355
Sep 30 - Oct 1
Total with taxes and fees
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

Harbor's Edge Motel

Harbor's Edge Motel

10/10 Excellent
"Clean room and peaceful area. Also within walking distance to many businesses and the marina. Highly recommend for a stay in Bayfield."
Megan 3-night trip
Posted 10 hours ago
Harbor's Edge 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 $147 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?

Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat: This vacation home rental outside of Ashland is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Ashland?

With 12 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, Northern Great Lakes Visitor Center and Apostle Islands National Lakeshore 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.