Ashland Holiday 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 holiday rentals

A modern kitchen with a wooden table and bar stools, a ceiling fan, and pendant lights.

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 NZ$317
includes taxes & fees
15 Nov - 16 Nov
South Apartment on Main Street
A modern living room with a blue sofa, wooden dining table, and a view of a parking lot through large windows.

2. 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.
North Apartment with Lake Superior Views
A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

3. 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 NZ$387
includes taxes & fees
16 Nov - 17 Nov
Mission Springs Resort
A modern kitchen with a central island, wooden stools, a stainless steel refrigerator, and a ceiling fan.

4. 2BR Lake Superior Stay | Hot Tub + Walk Downtown

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
The price is NZ$758
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.

5. 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 NZ$813
includes taxes & fees
30 Nov - 1 Dec
Historic Main St w/ Lake View | The Flatwater Loft
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

6. 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 NZ$576
includes taxes & fees
29 Nov - 30 Nov
Up North Oasis - Families & Dogs in the Bayfield Area
A cozy living room with a sofa, a coffee table, a fireplace, and a fan.

7. 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 NZ$765
includes taxes & fees
14 Nov - 15 Nov
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A bedroom with a large window, a bed with a white polka dot bedspread, and a view of a grassy yard and trees.

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 NZ$409
includes taxes & fees
14 Nov - 15 Nov
PORT 1 bedroom studio with AC just 2.5 miles from Bayfield
A bedroom with two beds, a dresser, a TV, and a door leading to another room.

9. 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 NZ$400
includes taxes & fees
17 Nov - 18 Nov
Lundy's Black Bear - Lemgrove
A room with a table and chairs, large windows, and a view of a building and water.

10. 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 NZ$407
includes taxes & fees
16 Nov - 17 Nov
Lower Flat @ Steeple Hill Flats, Bayfield
A covered porch with a table and chairs, a door, and a window.

11. 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 NZ$382
includes taxes & fees
15 Nov - 16 Nov
Cozy 1-bedroom condo located on the lake close to downtown.
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

12. 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 NZ$457
includes taxes & fees
19 Nov - 20 Nov
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

13. 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 NZ$473
includes taxes & fees
22 Nov - 23 Nov
Brookside Hide-A-Way #2, Port Superior, Bayfield
A cabin with a porch and outdoor seating area, surrounded by a gravel driveway and a wooden fence.

14. 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 NZ$419
includes taxes & fees
17 Nov - 18 Nov
Cozy Northwoods Cabin – Hiking, Waterfalls, UTV & ATV Trails, Sleeps 4
A wooden deck with a glass table and chairs overlooking a lake.

15. 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 NZ$580
includes taxes & fees
17 Nov - 18 Nov
Serenity Now | 4BR Trailside / Lakefront Cabin
A living room with a fireplace, sofas, a TV, and large windows.

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 NZ$652
includes taxes & fees
14 Nov - 15 Nov
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A beach with a wooden barrier and calm water reflecting sunlight.

17. 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 NZ$445
includes taxes & fees
19 Nov - 20 Nov
The Copper Squirrel is a secluded full log cabin on 10 acres.
A bedroom with a bed, a dresser, a TV, and a window.

18. 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 NZ$763
includes taxes & fees
22 Nov - 23 Nov
Downtown Bayfield Lodging in Historic Building
A wooden deck with a wicker lounge chair and a table, overlooking a forest.

19. 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 NZ$726
includes taxes & fees
15 Nov - 16 Nov
Woodland Chalet @ Brickyard Creek, Bayfield
A hotel room with a large bed, a sitting area with a view, and a bathtub.

20. Main @ Hendrickson House

Main @ Hendrickson House
Bayfield
10.0 out of 10, Exceptional, (3 reviews)
"The house was perfect for us. Very clean and had everything we needed to enjoy a relaxing 2 day getaway. I would definitely stay here again!!"
United States
Steven A.
The price is NZ$957
includes taxes & fees
15 Nov - 16 Nov
Main @ Hendrickson House
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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Find out more about Ashland

Everything you need to know about Ashland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland holiday rentals we have selected for you start as low as NZ$304 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

ENTIRE LAKEFRONT 10-bedroom Chateau Getaway at Whitecap Mountains Resort: This holiday home rental outside of Ashland is located on a lake, and has an indoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Ashland?

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