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

Ashland Holiday Rentals

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Our top choices for Ashland holiday 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 NZ$437
includes taxes & fees
25 Aug - 26 Aug
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 NZ$456
includes taxes & fees
7 Sept - 8 Sept
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 NZ$377
includes taxes & fees
11 Aug - 12 Aug
Mission Springs Resort

4. 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 NZ$361
includes taxes & fees
23 Aug - 24 Aug
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

5. 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)
"The apartment was very clean and well decorated. The host was very kind."
United States
Jennifer
The price is NZ$587
includes taxes & fees
9 Aug - 10 Aug
Upper level, one bedroom, one bath condo, with Lake Superior views.

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 NZ$396
includes taxes & fees
10 Aug - 11 Aug
Lundy's Black Bear - Blair Oaks

7. 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 NZ$665
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom studio in serene Bayfield with AC

8. 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, (33 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 NZ$441
includes taxes & fees
12 Aug - 13 Aug
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!

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

Annex No. 2 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (26 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 NZ$461
includes taxes & fees
1 Sept - 2 Sept
Annex No. 2 DePerrys | On Lake Superior Shoreline

10. 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 NZ$583
includes taxes & fees
28 Aug - 29 Aug
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!

11. Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (90 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 NZ$492
includes taxes & fees
9 Aug - 10 Aug
Avenue Side Room at The Copper Trout.

12. 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 traveller
The price is NZ$629
includes taxes & fees
12 Aug - 13 Aug
The Little Bodin

13. 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, (40 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 NZ$580
includes taxes & fees
27 Aug - 28 Aug
The Copper Squirrel is a secluded full log cabin on 10 acres.

14. 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 NZ$671
includes taxes & fees
8 Sept - 9 Sept
Up North Oasis - Families & Dogs in the Bayfield Area

15. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Washburn
9.2 out of 10, Wonderful, (36 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 NZ$1,127
includes taxes & fees
9 Aug - 10 Aug
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

16. Bayfield Island View `Fedora` on Lake Superior

Bayfield Island View `Fedora` on Lake Superior
Bayfield
9.8 out of 10, Exceptional, (35 reviews)
"Great place to stay on the water. Id stay here again!!"
United States
kris p.
The price is NZ$816
includes taxes & fees
16 Aug - 17 Aug
Bayfield Island View `Fedora` on Lake Superior

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

Annex No. 1 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful getaway, The property was perfect for my husband and I. Everything was as advertised."
United States
Sarah S.
The price is NZ$461
includes taxes & fees
1 Sept - 2 Sept
Annex No. 1 DePerrys | On Lake Superior Shoreline

18. Lundy's Black Bear - Rosewood

Lundy's Black Bear - Rosewood
Drummond
9.0 out of 10, Wonderful, (4 reviews)
"Conveniently located for my snowmobile trip and room was very nice and clean. Would definitely stay again."
United States
Curtis E.
The price is NZ$396
includes taxes & fees
10 Aug - 11 Aug
Lundy's Black Bear - Rosewood

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 NZ$396
includes taxes & fees
10 Aug - 11 Aug
Lundy's Black Bear - Lemgrove

20. 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 NZ$636
includes taxes & fees
7 Sept - 8 Sept
Bayfield Fruit Loop Retreat - Main Cottage
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Ashland holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Ashland. 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 Ashland. 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 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 holiday 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 Ashland short-term rentals, that won’t be hard to do.

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?

Fantastic building with AC in lovely Ashland: This highly rated holiday home rental in Ashland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.