Ashland Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Ashland vacation rentals

A paved path along a lakeside park with a playground and a building in the background.

1. South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (25 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is AED 364
AED 646 total
includes taxes & fees
15 Nov - 16 Nov
South Apartment on Main Street
A beach with a sandy shore, trees, and a body of water.

2. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (82 reviews)
"Clean room, great locations"
United States
Van
The price is AED 750
AED 791 total
includes taxes & fees
15 Nov - 16 Nov
Mission Springs Resort
A residential area with houses, a fire pit, and outdoor seating.

3. 2BR Lake Superior Stay | Hot Tub + Walk Downtown

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
The price is AED 588
AED 1,577 total
includes taxes & fees
19 Nov - 20 Nov
2BR Lake Superior Stay | Hot Tub + Walk Downtown
A brick building with a door and potted plants in front.

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, (6 reviews)
"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 1,028
AED 1,656 total
includes taxes & fees
30 Nov - 1 Dec
Historic Main St w/ Lake View | The Flatwater Loft
A compact living space with a kitchenette, a television, a ceiling fan, and a wooden cabinet.

5. Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint

Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint
Bayfield
10.0 out of 10, Exceptional, (2 reviews)
"The condo was very clean and everything you would need was there. Lisa was very responsive to any questions we had, and was very helpful. We would definitely recommend it to others."
United States
Carol
The price is AED 309
AED 622 total
includes taxes & fees
15 Nov - 16 Nov
Bayfield studio, NEW listing/freshly remodeled, Apostle Islands, charming/quaint
A bedroom with two beds, a dresser, a TV, and a door leading to another room.

6. 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 AED 419
AED 821 total
includes taxes & fees
15 Nov - 16 Nov
Lundy's Black Bear - Lemgrove
A dining table with food, a dog, and a chair on a porch.

7. Up North Oasis - Families & Dogs in the Bayfield Area

Up North Oasis - Families & Dogs in the Bayfield Area
Washburn
9.8 out of 10, Exceptional, (14 reviews)
"Nice house, and nice location."
United States
ben H.
The price is AED 533
AED 1,197 total
includes taxes & fees
29 Nov - 30 Nov
Up North Oasis - Families & Dogs in the Bayfield Area
A hotel room with a bed, a desk, a chair, a TV, and a window with a view of trees and water.

8. PORT 1 bedroom studio with AC just 2.5 miles from Bayfield

PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
Bayfield
10.0 out of 10, Exceptional, (1 review)
"Great location, nice view from bedroom. Easy in and out and good communication. Could use darker shades."
United States
scott d.
The price is AED 404
AED 843 total
includes taxes & fees
15 Nov - 16 Nov
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A cozy living room with a sofa, a coffee table, a fireplace, and a fan.

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, (45 reviews)
"Great location"
United States
vicki A
The price is AED 768
AED 1,592 total
includes taxes & fees
15 Nov - 16 Nov
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

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, (46 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 680
AED 942 total
includes taxes & fees
16 Nov - 17 Nov
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A room with a table and chairs, large windows, and a view of a building and water.

11. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (26 reviews)
"Nice and cozy with a great view. The outside spaces could use some tidying up and paint, but once inside the place was awesome."
United States
Lori
The price is AED 551
AED 832 total
includes taxes & fees
16 Nov - 17 Nov
Lower Flat @ Steeple Hill Flats, Bayfield
A cabin with a porch and outdoor seating area, surrounded by a gravel driveway and a wooden fence.

12. 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, (56 reviews)
"Everything was amazing! Will be back"
United States
Kimberly
The price is AED 750
AED 861 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
A beach with a wooden barrier and calm water reflecting sunlight.

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, (48 reviews)
"Great place to relax and close enough to Bayfield, a fun and charming seaport."
United States
Tad S.
The price is AED 654
AED 911 total
includes taxes & fees
19 Nov - 20 Nov
The Copper Squirrel is a secluded full log cabin on 10 acres.
A wooden deck with a glass table and chairs overlooking a lake.

14. Serenity Now | 4BR Trailside / Lakefront Cabin

Serenity Now | 4BR Trailside / Lakefront Cabin
Hurley
10.0 out of 10, Exceptional, (7 reviews)
"We had a great time. Wonderful place and a quiet neighborhood. Hosts were helpful and very responsive."
United States
kim f.
The price is AED 393
AED 1,190 total
includes taxes & fees
17 Nov - 18 Nov
Serenity Now | 4BR Trailside / Lakefront Cabin
A covered patio area with a table and chairs, a doormat, and a small garden area.

15. Cozy 1-bedroom condo located on the lake close to downtown.

Cozy 1-bedroom condo located on the lake close to downtown.
La Pointe
The price is AED 643
AED 780 total
includes taxes & fees
15 Nov - 16 Nov
Cozy 1-bedroom condo located on the lake close to downtown.
A room with a sofa, a lamp, and a view of a balcony with a railing.

16. 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, (24 reviews)
"Location and the host are incredible!"
United States
Michelle N.
The price is AED 643
AED 1,353 total
includes taxes & fees
15 Nov - 16 Nov
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A kitchen with a microwave, stove, and wooden cabinets. There's a dining table with chairs and a framed artwork above it.

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

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (42 reviews)
"Great place and wonderful rear deck. Wish we had more time to spend there."
United States
Don L.
The price is AED 643
AED 1,008 total
includes taxes & fees
15 Nov - 16 Nov
Brookside Hide-A-Way #2, Port Superior, Bayfield
A beach with clear skies, a sandy shore, a tree, and a dock with boats.

18. Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (67 reviews)
"Very clean and cozy cabin near Bayfield and Meyers beach"
United States
Reed C.
The price is AED 872
AED 1,508 total
includes taxes & fees
15 Nov - 16 Nov
Woodland Chalet @ Brickyard Creek, Bayfield
A wooden cabin interior with large windows, a dining table, and chairs.

19. Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield
Bayfield
10.0 out of 10, Exceptional, (84 reviews)
"Beautiful place!"
United States
Susan S.
The price is AED 941
AED 1,590 total
includes taxes & fees
15 Nov - 16 Nov
Northwoods Chalet @ Brickyard Creek, Bayfield
A waterfront property with a covered patio, a brick building, and a view of the sea.

20. Downtown Bayfield Lodging in Historic Building

Downtown Bayfield Lodging in Historic Building
Bayfield
9.2 out of 10, Wonderful, (5 reviews)
"Loved the rooms! Enjoyed the views of the lake and the quaint downtown area. It was a very quiet and enjoyable stay. I gave it 4 stars only because the sofa was so hard and uncomfortable. We stayed in 2 nights to watch the Brewers play (YAY!) but it was very difficult to get comfortable on the sofa and no amount of throw pillows could change that. That being said, the bed was a dream and the kitchen well appointed. Would I stay there again? Maybe if the sofa was swapped out."
United States
Susan
The price is AED 941
AED 1,618 total
includes taxes & fees
15 Nov - 16 Nov
Downtown Bayfield Lodging in Historic Building
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

A modern building with a unique architectural design, situated on a rocky shoreline with a body of water in the foreground.
Blue Wave Inn

Blue Wave Inn

Blue Wave Inn
Ashland

10/10 Excellent

The Inn is right on the water, and we had a very spacious and charming room! There’s a nice coffee shop and great little boutique there. We look forward to returning some day!
United States
Constance
Reviewed August 19, 2024
Blue Wave Inn

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?

ENTIRE LAKEFRONT 10-bedroom Chateau Getaway at Whitecap Mountains Resort: This vacation home rental outside of Ashland is located on a lake and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Ashland?

With 13 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, Chequamegon Bay Golf Course and Northern Great Lakes Visitor Center 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.