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

Holiday Rentals in Ashland

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Ashland holiday rentals

A spacious living room with a fireplace, a sofa, and a dining area with a table and chairs.

1. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (79 reviews)
"A little older cabin than we thought but quaint. Quiet and clean. I would recommend this"
United States
Brian r
The price is €147
includes taxes & fees
21 Oct - 22 Oct
Mission Springs Resort
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.
The price is €241
includes taxes & fees
8 Oct - 9 Oct
North Apartment with Lake Superior Views
A modern kitchen with a wooden table and bar stools, a ceiling fan, and pendant lights.

3. 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 €196
includes taxes & fees
5 Oct - 6 Oct
South Apartment on Main Street
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, (2 reviews)
"Awesome location, great communication with host,Flat was newly decorated in 40’s deco. Loved loved the charm of the flat."
United States
Judy D.
The price is €628
includes taxes & fees
22 Oct - 23 Oct
Historic Main St w/ Lake View | The Flatwater Loft
A living room with a blue accent wall, a round mirror, a white sofa with blue cushions, a brown leather ottoman, and a white shelving unit with decorative items.

5. Lake Superior Stay - Fire Pit Patio - Pet Friendly

Lake Superior Stay - Fire Pit Patio - Pet Friendly
Ashland
9.8 out of 10, Exceptional, (9 reviews)
"Cute place "
United States
Donald B.
The price is €461
includes taxes & fees
18 Oct - 19 Oct
Lake Superior Stay - Fire Pit Patio - Pet Friendly
A gray storage unit with a metal ladder and a black fan on a concrete patio.

6. 2BR Lake Superior Stay | Hot Tub + Walk Downtown

2BR Lake Superior Stay | Hot Tub + Walk Downtown
Ashland
The price is €424
includes taxes & fees
1 Nov - 2 Nov
2BR Lake Superior Stay | Hot Tub + Walk Downtown
A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

7. 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, (11 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 €311
includes taxes & fees
1 Nov - 2 Nov
Up North Oasis - Families & Dogs in the Bayfield Area
A gazebo with a snow-covered ground, a bench, and a railing.

8. Applefest Bayfield available this w/e @discount, near town/fireplace/jacuzzi

Applefest Bayfield available this w/e @discount, near town/fireplace/jacuzzi
Bayfield
9.8 out of 10, Exceptional, (261 reviews)
"Very cute condo. Close to the city."
United States
Cindy B.
The price is €202
includes taxes & fees
7 Oct - 8 Oct
Applefest Bayfield available this w/e @discount, near town/fireplace/jacuzzi
Exterior

9. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (69 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 €334
includes taxes & fees
7 Oct - 8 Oct
The Little Bodin
A backyard with a wooden deck, stepping stones, raised garden beds with flowers, and a chair.

10. 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, (41 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 €409
includes taxes & fees
5 Oct - 6 Oct
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
A bedroom with a bed, bedside table, lamp, and a dresser with a coffee maker.

11. Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (93 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 €260
includes taxes & fees
5 Oct - 6 Oct
Avenue Side Room at The Copper Trout.
A living room with a fireplace, sofas, a TV, and large windows.

12. 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, (20 reviews)
"Great property…. Very clean woth comfortable beds. Great location!"
United States
Marj J.
The price is €315
includes taxes & fees
8 Oct - 9 Oct
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
A room with a table and chairs, large windows, and a view of a building and water.

13. Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (25 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 €212
includes taxes & fees
1 Nov - 2 Nov
Lower Flat @ Steeple Hill Flats, Bayfield
A dining area with a table, chairs, and a large window with a view of a green landscape.

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

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
9.4 out of 10, Exceptional, (8 reviews)
The price is €239
includes taxes & fees
6 Oct - 7 Oct
Cozy 1-bedroom studio in serene Bayfield with AC
A bedroom with two beds, a ceiling fan, a wall-mounted clock, and a bathroom visible through an open door.

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

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.8 out of 10, Exceptional, (41 reviews)
"Great place and wonderful rear deck. Wish we had more time to spend there."
United States
Don L.
The price is €213
includes taxes & fees
1 Nov - 2 Nov
Brookside Hide-A-Way #2, Port Superior, Bayfield
A covered porch with a blue railing, a door labeled "Annex 1", and two chairs.

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

Annex No. 1 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (48 reviews)
"Cute and cozy little place! Perfect for our anniversary weekend getaway!"
United States
Kabao
The price is €223
includes taxes & fees
6 Oct - 7 Oct
Annex No. 1 DePerrys | On Lake Superior Shoreline
A deck with two Adirondack chairs, a door, and a window.

17. Suite One at La Pointe Lodging

Suite One at La Pointe Lodging
La Pointe
9.8 out of 10, Exceptional, (28 reviews)
"Lovely place!!"
United States
Anne R.
The price is €283
includes taxes & fees
8 Oct - 9 Oct
Suite One at La Pointe Lodging
Stunning sunrise & sunset views

18. Outer Island Apartment @ The Copper Crown

Outer Island Apartment @ The Copper Crown
Bayfield
9.8 out of 10, Exceptional, (15 reviews)
"Great location and nice little space to stay near the downtown area."
United States
Rickandheather H.
The price is €332
includes taxes & fees
12 Oct - 13 Oct
Outer Island Apartment @ The Copper Crown
A round table with a dark tablecloth and a decorative piece on it, surrounded by wooden chairs. A large window offers a view of a body of water and trees.

19. 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, (122 reviews)
"Great property! wonderful rejuvenation time for myself and my family"
United States
Brian
The price is €540
includes taxes & fees
18 Oct - 19 Oct
Lake Shore Home with private dock and large deck--1 mile from Bayfield
A modern cabin with a sloped roof, large windows, and a deck area with seating and potted plants.

20. 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, (41 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 €305
includes taxes & fees
14 Oct - 15 Oct
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
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

Hotel Chequamegon, BW Signature Collection

Hotel Chequamegon, BW Signature Collection

10/10 Excellent
"We thought that the food was really good, and the staff was very helpful! We had a long drive in, over six hours, and we were able to check in a little early, which was super helpful! The breakfast attendants were always doing a great job making sure there was fresh food and asking how things were. We had a couple questions that we asked the front desk, and they try to be as helpful as they could. The view was beautiful! We would definitely stay here again!"
Kevin 3-night trip
Posted 12 hours ago
Hotel Chequamegon, BW Signature Collection

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, apart-hotels, 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 €147 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.