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
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

TV

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
$199 nightly
The price is $219
Sep 13 - Sep 14
Total with taxes and fees
South Apartment on Main Street
TV

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.
$248 nightly
The price is $273
Sep 20 - Sep 21
Total with taxes and fees
North Apartment with Lake Superior Views
Flat-screen TV, DVD player

3. 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
Exterior

4. 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.
$521 nightly
The price is $573
Sep 21 - Sep 22
Total with taxes and fees
Historic Main St w/ Lake View | The Flatwater Loft
Property grounds

5. 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, (257 reviews)
"Wonderful clean and well appointed place!"
United States
Kinda S.
$182 nightly
The price is $204
Sep 13 - Sep 14
Total with taxes and fees
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Property grounds

6. 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.
$326 nightly
The price is $365
Sep 16 - Sep 17
Total with taxes and fees
All season cottage overlooking the private beach on Lake Superior
Dining

7. 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 12 - Sep 13
Total with taxes and fees
Cozy 1-bedroom studio in serene Bayfield with AC
Property grounds

8. 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, (11 reviews)
"Very friendly and responsive owners. Very comfortable stay!"
United States
Grace A.
$141 nightly
The price is $160
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
Property grounds

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, (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
Microwave, oven, stovetop, dishwasher

10. 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 4 - Oct 5
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
1 bedroom, iron/ironing board, WiFi (free), bed sheets

11. Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks
Drummond
10.0 out of 10, Exceptional, (5 reviews)
"😀"
United States
Lynne
$205 nightly
The price is $224
Sep 13 - Sep 14
Total with taxes and fees
Lundy's Black Bear - Blair Oaks
Terrace/patio

12. 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
1 bedroom, desk, WiFi, bed sheets

13. Brookside Hide-A-Way #2, Port Superior, Bayfield

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (39 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
Interior

14. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.0 out of 10, Wonderful, (21 reviews)
"Great view"
United States
Bruce F.
$212 nightly
The price is $244
Oct 10 - Oct 11
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, Bayfield
TV

15. 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, (19 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
Exterior

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, (43 reviews)
"The cabin was beautiful and perfect for our stay. Would absolutely stay here again!"
United States
Katie E.
$225 nightly
The price is $237
Sep 13 - Sep 14
Total with taxes and fees
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
1 bedroom, WiFi, bed sheets

17. 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.
$243 nightly
The price is $277
Sep 12 - Sep 13
Total with taxes and fees
Lake Side Room at The Copper Trout.
Exterior

18. 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
$333 nightly
The price is $380
Sep 13 - Sep 14
Total with taxes and fees
The Little Bodin
Exterior

19. 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
$331 nightly
The price is $349
Sep 28 - Sep 29
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Beach nearby

20. 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, (42 reviews)
"Gorgeous cabin in the Northwoods, with all the comforts of home. We loved the screened porch for the warm afternoons and appreciated the wood stove for cozy nights."
United States
Crystal B.
$332 nightly
The price is $350
Oct 8 - Oct 9
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
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
"Convenient, great views of the water on the deck and helpful staff We keep coming back year after year!"
Kathleen 3-night trip
Posted 1 hour 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 $204 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?

The Maki House: This vacation home rental outside of Ashland is located near skiing and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.