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

Ashland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Ashland vacation rentals

TV

1. 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 AED 588
AED 1,020 total
includes taxes & fees
9 Sep - 10 Sep
North Apartment with Lake Superior Views
TV

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
The price is AED 584
AED 971 total
includes taxes & fees
24 Aug - 25 Aug
South Apartment on Main Street
Flat-screen TV, DVD player

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 AED 846
AED 893 total
includes taxes & fees
8 Sep - 9 Sep
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, (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.
The price is AED 1,587
AED 2,465 total
includes taxes & fees
27 Aug - 28 Aug
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, (252 reviews)
"Wonderful clean and well appointed place!"
United States
Kinda S.
The price is AED 437
AED 769 total
includes taxes & fees
23 Aug - 24 Aug
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
1 bedroom, iron/ironing board, WiFi (free), bed sheets

6. 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 AED 419
AED 869 total
includes taxes & fees
16 Aug - 17 Aug
Lundy's Black Bear - Blair Oaks
Beach towels

7. 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, (60 reviews)
"Great location, great fit for our get away."
United States
Zach L.
The price is AED 716
AED 1,309 total
includes taxes & fees
13 Aug - 14 Aug
Upper level, one bedroom, one bath condo, with Lake Superior views.
Microwave, oven, stovetop, dishwasher

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, (9 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 AED 694
AED 1,469 total
includes taxes & fees
8 Sep - 9 Sep
Up North Oasis - Families & Dogs in the Bayfield Area
Interior

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 AED 655
AED 1,021 total
includes taxes & fees
1 Sep - 2 Sep
Annex No. 2 DePerrys | On Lake Superior Shoreline
Exterior

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, (34 reviews)
"Property was very clean, very nice amenities and accommodations, comfortable bed, centrally located to many areas to explore! Hosts were very resposive and helpful with any questions! "
United States
Scott D.
The price is AED 790
AED 954 total
includes taxes & fees
12 Aug - 13 Aug
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
Dining

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

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
9.6 out of 10, Exceptional, (4 reviews)
"Great place and accurate to listing"
United States
Olivia M.
The price is AED 801
AED 1,448 total
includes taxes & fees
8 Sep - 9 Sep
Cozy 1-bedroom studio in serene Bayfield with AC
1 bedroom, WiFi, bed sheets

12. 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 AED 823
AED 1,072 total
includes taxes & fees
12 Aug - 13 Aug
Avenue Side Room at The Copper Trout.
Exterior

13. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (57 reviews)
"It was a perfect spot in a wonderful little town. "
United States
Anonymous traveler
The price is AED 882
AED 1,499 total
includes taxes & fees
30 Aug - 31 Aug
The Little Bodin
Beach nearby

14. 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 AED 918
AED 1,279 total
includes taxes & fees
27 Aug - 28 Aug
The Copper Squirrel is a secluded full log cabin on 10 acres.
Exterior

15. 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 AED 918
AED 1,279 total
includes taxes & fees
28 Aug - 29 Aug
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Property grounds

16. 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 AED 1,175
AED 2,197 total
includes taxes & fees
11 Sep - 12 Sep
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Interior

17. Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (64 reviews)
"Great place! Secluded and yet close to town."
United States
Anonymous traveler
The price is AED 1,077
AED 1,863 total
includes taxes & fees
12 Aug - 13 Aug
Woodland Chalet @ Brickyard Creek, Bayfield
Beach

18. Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (56 reviews)
"Super close to town and easy to access. We enjoyed our stay!"
United States
Kerry B.
The price is AED 1,532
AED 1,963 total
includes taxes & fees
17 Aug - 18 Aug
Bayfield Fruit Loop Retreat - Main Cottage
1 bedroom, iron/ironing board, WiFi (free), bed sheets

19. Lundy's Black Bear - Lemgrove

Lundy's Black Bear - Lemgrove
Drummond
8.8 out of 10, Excellent, (3 reviews)
"Newly constructed with only 3 units so very quiet."
United States
Cheryl A.
The price is AED 419
AED 869 total
includes taxes & fees
12 Aug - 13 Aug
Lundy's Black Bear - Lemgrove
Smart TV, books

20. 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 AED 1,186
AED 1,775 total
includes taxes & fees
16 Aug - 17 Aug
Bayfield Island View `Fedora` on Lake Superior
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

Legendary Waters Resort & Casino

Legendary Waters Resort & Casino

10/10 Excellent
"Beautiful place. Clean and very comfy bed. View of Lake from resort. Nice restaurant also at resort. Swam in pool and hot tub that goes indoors and out..very well maintained motel. Will stay again. 10/10"
Dawn 1-night trip
Posted 16 hours ago
Legendary Waters Resort & Casino

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?

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.