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

Ashland Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Ashland vacation rentals

A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

1. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (78 reviews)
"A little older cabin than we thought but quaint. Quiet and clean. I would recommend this"
United States
Brian r
$237 nightly
The price is $250
Sep 15 - Sep 16
Total with taxes and fees
Mission Springs Resort
A modern kitchen with a wooden table and bar stools, a ceiling fan, and pendant lights.

2. 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
$199 nightly
The price is $219
Sep 13 - Sep 14
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.

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.
$248 nightly
The price is $273
Sep 20 - Sep 21
Total with taxes and fees
North Apartment with Lake Superior Views
A wooden deck with a view of the ocean and a full moon.

4. 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, (20 reviews)
"Clean, quiet, beautiful private beach! "
United States
Abby K.
$372 nightly
The price is $417
Sep 16 - Sep 17
Total with taxes and fees
All season cottage overlooking the private beach on Lake Superior
A beach scene with the sun setting over the ocean.

5. # 1 Lakeside

# 1 Lakeside
La Pointe
10.0 out of 10, Exceptional, (143 reviews)
"Beautiful view of the lake from the patio and from the living room. Very comfortable and clean. Lovely place to stay."
United States
Greg L.
$482 nightly
The price is $547
Sep 13 - Sep 14
Total with taxes and fees
# 1 Lakeside
A backyard with a wooden deck, stepping stones, raised garden beds with flowers, and a chair.

6. 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, (40 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
Sep 13 - Sep 14
Total with taxes and fees
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A cabin with a porch and outdoor seating area, surrounded by a gravel driveway and a wooden fence.

7. 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, (41 reviews)
"The cabin was beautiful and perfect for our stay. Would absolutely stay here again!"
United States
Katie E.
$224 nightly
The price is $236
Sep 13 - Sep 14
Total with taxes and fees
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

8. 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, (10 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.
$335 nightly
The price is $375
Oct 5 - Oct 6
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
A round table with a dark tablecloth and a decorative piece on it, surrounded by wooden chairs. A large window offers a view of a body of water and trees.

9. Lake Shore Home with private dock and large deck--1 mile from Bayfield

Lake Shore Home with private dock and large deck--1 mile from Bayfield
Bayfield
10.0 out of 10, Exceptional, (120 reviews)
"Great property! wonderful rejuvenation time for myself and my family"
United States
Brian
$680 nightly
The price is $762
Sep 17 - Sep 18
Total with taxes and fees
Lake Shore Home with private dock and large deck--1 mile from Bayfield

10. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (65 reviews)
"Great central location in downtown Bayfield. Very clean. Perfect for our family of four’s long weekend in Bayfield."
United States
Andrew
$331 nightly
The price is $377
Sep 9 - Sep 10
Total with taxes and fees
The Little Bodin
A living room with a sofa, wooden chairs, a coffee table, a TV, and a bookshelf.

11. Bayfield Island View `Fedora` on Lake Superior

Bayfield Island View `Fedora` on Lake Superior
Bayfield
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay on the water. Id stay here again!!"
United States
kris p.
Bayfield Island View `Fedora` on Lake Superior
A bedroom with a bed, a bedside table, a lamp, and a window with blinds.

12. Lake Side Room at The Copper Trout.

Lake Side Room at The Copper Trout.
Bayfield
9.2 out of 10, Wonderful, (109 reviews)
"Room was clean and in a great location for enjoying the greater Bayfield area."
United States
Sally R.
$255 nightly
The price is $291
Sep 9 - Sep 10
Total with taxes and fees
Lake Side Room at The Copper Trout.
A backyard with a fire pit, a chair, and a grill.

13. Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach

Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach
La Pointe
10.0 out of 10, Exceptional, (10 reviews)
"Very friendly and responsive owners. Very comfortable stay!"
United States
Grace A.
$150 nightly
The price is $170
Sep 20 - Sep 21
Total with taxes and fees
Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach
A living room with a fireplace, sofas, a TV, and large windows.

14. 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, (18 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
$315 nightly
The price is $359
Oct 8 - Oct 9
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
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, (38 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 covered porch with a blue railing, a door labeled "Annex 1", and two chairs.

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

Annex No. 1 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (45 reviews)
"Cute and cozy little place! Perfect for our anniversary weekend getaway!"
United States
Kabao
$232 nightly
The price is $247
Oct 4 - Oct 5
Total with taxes and fees
Annex No. 1 DePerrys | On Lake Superior Shoreline
A dining area with a table, chairs, and a large window with a view of a green landscape.

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

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
9.0 out of 10, Wonderful, (6 reviews)
$315 nightly
The price is $353
Oct 3 - Oct 4
Total with taxes and fees
Cozy 1-bedroom studio in serene Bayfield with AC
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

18. 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, (40 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
$332 nightly
The price is $350
Sep 16 - Sep 17
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A cabin with a wooden deck and a snow-covered roof, surrounded by snow-laden trees.

19. Bayfield Fruit Loop Retreat -2 Cottages

Bayfield Fruit Loop Retreat -2 Cottages
Bayfield
9.8 out of 10, Exceptional, (8 reviews)
"These cottages are the cleanest we have ever stayed in. Great for groups because of the cottage locations. Amenities were absolutely complete and perfect!"
United States
Tami N.
$659 nightly
The price is $738
Oct 5 - Oct 6
Total with taxes and fees
Bayfield Fruit Loop Retreat -2 Cottages
A bedroom with two beds, a wooden dresser, a TV mounted on the wall, and a red door.

20. Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks
Drummond
10.0 out of 10, Exceptional, (5 reviews)
"😀"
United States
Lynne
$212 nightly
The price is $232
Sep 13 - Sep 14
Total with taxes and fees
Lundy's Black Bear - Blair Oaks
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Super 8 by Wyndham Ashland

Super 8 by Wyndham Ashland

8/10 Good
"It was an overnight stay; staff friendly, room very clean. Thanks."
Eppy 1-night trip
Posted less than an hour ago
Super 8 by Wyndham Ashland

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 $236 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?

Private Beach and Endless Water : This vacation home rental outside of Ashland is located on a lake and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.