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

Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

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
The price is CA $173
CA $301 total
includes taxes & fees
Sep 13 - Sep 14
South Apartment on Main Street

2. North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (45 reviews)
"Great location, clean and comfortable. "
United States
Heather Ann M.
The price is CA $222
CA $378 total
includes taxes & fees
Sep 9 - Sep 10
North Apartment with Lake Superior Views

3. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (76 reviews)
"Cottage 4 was a blend of rustic charm and recent updates. The beds and furniture were comfortable. We were a party of two, but it would have been roomy for four. The hosts’ welcome gift of local ice cream was a bonus. The location worked well for us. It was just off the highway, but quiet; and we had easy drives to explore towns and trails in the area."
United States
Kathleen
The price is CA $288
CA $304 total
includes taxes & fees
Sep 15 - Sep 16
Mission Springs Resort

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, (1 review)
"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.
Historic Main St w/ Lake View | The Flatwater Loft

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, (253 reviews)
"Wonderful clean and well appointed place!"
United States
Kinda S.
The price is CA $160
CA $280 total
includes taxes & fees
Aug 23 - Aug 24
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

6. 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)
"Great location, clean, owners were responsive and helped with any issues. I would stay here again. "
United States
Angela M.
The price is CA $208
CA $268 total
includes taxes & fees
Sep 13 - Sep 14
Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach

7. Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks
Drummond
10.0 out of 10, Exceptional, (4 reviews)
"Extremely quiet and peaceful stay! Very nice motel and location."
United States
Tom H.
The price is CA $158
CA $324 total
includes taxes & fees
Aug 19 - Aug 20
Lundy's Black Bear - Blair Oaks

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 wonderful stay and will be coming back here next time we’re in the area. We found some great hikes!"
United States
Joan Q.
The price is CA $262
CA $552 total
includes taxes & fees
Sep 8 - Sep 9
Up North Oasis - Families & Dogs in the Bayfield Area

9. Annex No. 2 DePerrys | On Lake Superior Shoreline

Annex No. 2 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (27 reviews)
"Great stay for two nights. Amazing views and really close to both Bayfield and Meyers beach which we enjoyed! Accommodations were clean and easy check in and out"
United States
Jeffrey P.
The price is CA $247
CA $383 total
includes taxes & fees
Sep 1 - Sep 2
Annex No. 2 DePerrys | On Lake Superior Shoreline

10. Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!

Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
Mellen
10.0 out of 10, Exceptional, (36 reviews)
"Beautiful house!! Looks better in person. Very clean, well maintained. The outside is just as nice. Appreciated the complimentary snacks!"
United States
Dawn
The price is CA $298
CA $357 total
includes taxes & fees
Aug 19 - Aug 20
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!

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

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
8.8 out of 10, Excellent, (5 reviews)
The price is CA $294
CA $528 total
includes taxes & fees
Sep 16 - Sep 17
Cozy 1-bedroom studio in serene Bayfield with AC

12. Upper level, one bedroom, one bath condo, with Lake Superior views.

Upper level, one bedroom, one bath condo, with Lake Superior views.
La Pointe
10.0 out of 10, Exceptional, (61 reviews)
"Great location, great fit for our get away."
United States
Zach L.
The price is CA $329
CA $568 total
includes taxes & fees
Aug 20 - Aug 21
Upper level, one bedroom, one bath condo, with Lake Superior views.

13. Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (91 reviews)
"The room was awesome - all that we needed. Right in town so very walkable. We would definitely stay here again when we are in the area."
United States
Brendon
The price is CA $311
CA $402 total
includes taxes & fees
Aug 19 - Aug 20
Avenue Side Room at The Copper Trout.

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, (37 reviews)
"We had a great time! Beautiful home with easy access to all the South Shore has to offer. "
United States
Anastasia Hopkins F.
The price is CA $444
CA $831 total
includes taxes & fees
Sep 11 - Sep 12
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

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, (41 reviews)
"Super cute and cozy cabin. Great base camp for waterfall explorations. Kristin was great to work with and even made sure the woodstove was blazing for our arrival. I also loved all the handmade pottery decorating the space. It was too chilly to be outside much but we did see the turtles and had a greeting from a barred owl one evening. "
United States
Peg C.
The price is CA $347
CA $477 total
includes taxes & fees
Aug 27 - Aug 28
The Copper Squirrel is a secluded full log cabin on 10 acres.

16. 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
The price is CA $347
CA $477 total
includes taxes & fees
Sep 16 - Sep 17
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!

17. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (61 reviews)
"Great central location in downtown Bayfield. Very clean. Perfect for our family of four’s long weekend in Bayfield."
United States
Andrew
The price is CA $300
CA $517 total
includes taxes & fees
Aug 31 - Sep 1
The Little Bodin

18. Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods
Bayfield
10.0 out of 10, Exceptional, (48 reviews)
"We had a wonderful stay! The cabin was stocked with anything you would need, vey clean, and excellent accommodations! Would love to stay again next time we visit!"
United States
Stacey L.
The price is CA $469
CA $598 total
includes taxes & fees
Sep 3 - Sep 4
Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

19. Bayfield Island View `Fedora` on Lake Superior

Bayfield Island View `Fedora` on Lake Superior
Bayfield
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay on the water. Id stay here again!!"
United States
kris p.
The price is CA $448
CA $664 total
includes taxes & fees
Aug 26 - Aug 27
Bayfield Island View `Fedora` on Lake Superior

20. 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.
The price is CA $158
CA $324 total
includes taxes & fees
Aug 19 - Aug 20
Lundy's Black Bear - Lemgrove
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

Find out more about Ashland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Fantastic building with AC in lovely Ashland: Visitors give good reviews to this Ashland vacation home rental, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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?

Lake Superior and Ore Dock Park 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.