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

Ashland Holiday Rentals

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Check prices for these dates

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

Our top choices for Ashland holiday rentals

Living area

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
The price is HK$1,365
HK$1,440 total
includes taxes & fees
4 Oct - 5 Oct
Mission Springs Resort
Living area

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 HK$980
HK$1,717 total
includes taxes & fees
13 Sept - 14 Sept
South Apartment on Main Street
Living area

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.
The price is HK$1,254
HK$2,143 total
includes taxes & fees
20 Sept - 21 Sept
North Apartment with Lake Superior Views
Property grounds

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.
The price is HK$1,568
HK$3,267 total
includes taxes & fees
16 Sept - 17 Sept
All season cottage overlooking the private beach on Lake Superior
Beach

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.
The price is HK$3,332
HK$4,325 total
includes taxes & fees
13 Sept - 14 Sept
# 1 Lakeside
Property grounds

6. 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, (39 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 HK$1,639
HK$3,601 total
includes taxes & fees
13 Sept - 14 Sept
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Exterior

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.
The price is HK$1,545
HK$1,854 total
includes taxes & fees
13 Sept - 14 Sept
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
Private kitchen

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.
The price is HK$1,349
HK$2,986 total
includes taxes & fees
5 Oct - 6 Oct
Up North Oasis - Families & Dogs in the Bayfield Area
Dining

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
The price is HK$3,332
HK$6,024 total
includes taxes & fees
22 Sept - 23 Sept
Lake Shore Home with private dock and large deck--1 mile from Bayfield
Exterior

10. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (64 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 HK$1,694
HK$2,959 total
includes taxes & fees
8 Sept - 9 Sept
The Little Bodin
Living area

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.
The price is HK$2,532
HK$3,763 total
includes taxes & fees
9 Sept - 10 Sept
Bayfield Island View `Fedora` on Lake Superior
Room

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.
The price is HK$1,757
HK$2,262 total
includes taxes & fees
8 Sept - 9 Sept
Lake Side Room at The Copper Trout.
Property grounds

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.
The price is HK$1,019
HK$1,335 total
includes taxes & fees
20 Sept - 21 Sept
Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach
Living area

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, (17 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
The price is HK$1,176
HK$2,816 total
includes taxes & fees
8 Oct - 9 Oct
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
Room

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.
The price is HK$1,352
HK$2,235 total
includes taxes & fees
7 Oct - 8 Oct
Brookside Hide-A-Way #2, Port Superior, Bayfield
Terrace/patio

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
The price is HK$1,217
HK$1,954 total
includes taxes & fees
4 Oct - 5 Oct
Annex No. 1 DePerrys | On Lake Superior Shoreline
Dining

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)
The price is HK$1,631
HK$2,995 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 1-bedroom studio in serene Bayfield with AC
Exterior

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
The price is HK$1,960
HK$2,746 total
includes taxes & fees
16 Sept - 17 Sept
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Exterior

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.
The price is HK$4,522
HK$5,785 total
includes taxes & fees
5 Oct - 6 Oct
Bayfield Fruit Loop Retreat -2 Cottages
Room

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
The price is HK$894
HK$1,829 total
includes taxes & fees
8 Sept - 9 Sept
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.
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Top Ashland Hotel Reviews

Whitecap Mountains Resort

Whitecap Mountains Resort

8/10 Good
"First of all, don't use google maps if you are arriving in the dark! Google told us we had "arrived at our location" and we had no idea where we were except on a dark, county road. The signage to the hotel from the county road is NON-EXISTENT. Next, this is a ski lodge, so imagine a room that gets pretty beat up by guests during the winter. (We stayed here during the summer.) Don't expect any nearby restaurants, because there are none--at least in the summer. But it was a place to stay. The room was fairly clean but could used some updating."
John 1-night trip
Posted 7 hours ago
Whitecap Mountains Resort

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

  • View our selection of featured holiday rentals in Ashland
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  • Enter your travel dates to view the best deals on holiday rentals in Ashland while they last

Look no further and take a look at our great range of rental properties in Ashland!

Frequently asked questions

Are there holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to Ashland Mural Walk, or you can select a more secluded option if you're looking for 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 are some of the best holiday rentals that Ashland has to offer?

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

How many holiday rentals are there in Ashland?

With 12 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.