Holiday Rentals in Ashland

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Our top choices for Ashland holiday rentals

Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (72 reviews)
"Love this place! Very cute and right on Lake Superior. Also love the ice cream stocked in the freezer from a local dairy!"
United States
Kimber
The price is €185
includes taxes & fees
26 May - 27 May
Mission Springs Resort

North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (43 reviews)
"A modern farmhouse style, perfect amount of amenities, clean and spacious. Great location."
United States
Maura
The price is €226
includes taxes & fees
31 May - 1 Jun
North Apartment with Lake Superior Views

South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (23 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is €162
includes taxes & fees
20 May - 21 May
South Apartment on Main Street

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, (20 reviews)
"Super clean, super comfortable, perfect peaceful location."
United States
Chris C.
The price is €181
includes taxes & fees
17 May - 18 May
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!

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, (111 reviews)
"Beautiful views, great location and proximity to Bayfield. Loved our stay. Will be back in the fall! "
United States
Monica O.
The price is €431
includes taxes & fees
17 May - 18 May
Lake Shore Home with private dock and large deck--1 mile from Bayfield

Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (86 reviews)
"Clean room, nice location."
United States
Kyle E.
The price is €252
includes taxes & fees
20 May - 21 May
Avenue Side Room at The Copper Trout.

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

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.6 out of 10, Exceptional, (35 reviews)
"Everything was clean, good communication. Enjoyable stay!"
United States
Robyn G.
The price is €248
includes taxes & fees
17 May - 18 May
Brookside Hide-A-Way #2, Port Superior, Bayfield

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 €503
includes taxes & fees
21 May - 22 May
Bayfield Fruit Loop Retreat -2 Cottages

Annex No. 1 DePerrys | On Lake Superior Shoreline

Annex No. 1 DePerrys | On Lake Superior Shoreline
Bayfield
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful getaway, The property was perfect for my husband and I. Everything was as advertised."
United States
Sarah S.
The price is €216
includes taxes & fees
18 May - 19 May
Annex No. 1 DePerrys | On Lake Superior Shoreline

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

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Washburn
9.4 out of 10, Exceptional, (32 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 €552
includes taxes & fees
3 Jun - 4 Jun
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

Outer Island Apartment @ The Copper Crown

Outer Island Apartment @ The Copper Crown
Bayfield
9.8 out of 10, Exceptional, (9 reviews)
"Loved the property and the sunrise view is spectacular. "
United States
Perry R.
The price is €326
includes taxes & fees
17 May - 18 May
Outer Island Apartment @ The Copper Crown

All season cottage with sauna overlooking the private beach on Lake Superior

All season cottage with sauna overlooking the private beach on Lake Superior
Washburn
10.0 out of 10, Exceptional, (17 reviews)
"The lakefront property has breathtaking views of south shore "
United States
BRIAN
The price is €295
includes taxes & fees
19 May - 20 May
All season cottage with sauna overlooking the private beach on Lake Superior

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, (234 reviews)
"Great stay and host! "
United States
Jenna Q.
The price is €226
includes taxes & fees
6 Jun - 7 Jun
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2

Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
Upson
10.0 out of 10, Exceptional, (1 review)
"A large group of us rented the Davos Chalet for a long weekend. There was more than enough room for us all. The common area was great for us to eat meals and hang out. The kids loved the game room in the basement. "
United States
Stacy H.
The price is €1,480
includes taxes & fees
17 May - 18 May
Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2

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, (1 review)
"The property is very conveniently located. Easy walk to downtown Bayfield and just 2 blocks from the Madeleine Island ferry dock. The condo is a flat which provides windows on all sides and sunlight all day long, along with a nice view of the lake directly to the east. The condo is also very nicely furnished and the kitchen is fully stocked with everything you would need to cook full meals if you wish to bring your own food. We’re already looking forward to our next trip!"
United States
Shawn W.
The price is €306
includes taxes & fees
17 May - 18 May
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

Great Northwoods home with access to all your recreational activities!

Great Northwoods home with access to all your recreational activities!
Mellen
9.8 out of 10, Exceptional, (14 reviews)
"It is a very spacious home near many fun attractions. Would be great for a friends getaway or fanily vacation. "
United States
Susan
The price is €200
includes taxes & fees
18 May - 19 May
Great Northwoods home with access to all your recreational activities!

Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (53 reviews)
"Super close to town and easy to access. We enjoyed our stay!"
United States
Kerry B.
The price is €321
includes taxes & fees
21 May - 22 May
Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods
Bayfield
10.0 out of 10, Exceptional, (41 reviews)
"We had a wonderful stay! The cabin was stocked with anything you would need, vey clean, and excellent accommodations! Would love to stay again next time we visit!"
United States
Stacey L.
The price is €315
includes taxes & fees
3 Jun - 4 Jun
Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

Lower Flat @ Steeple Hill Flats, Bayfield

Lower Flat @ Steeple Hill Flats, Bayfield
Bayfield
9.2 out of 10, Wonderful, (15 reviews)
"Great location, had everything we needed, and loved the view of Lake Superior, and the soaking tub!"
United States
Tina W.
The price is €222
includes taxes & fees
17 May - 18 May
Lower Flat @ Steeple Hill Flats, Bayfield

Lundy's Black Bear - Rosewood

Lundy's Black Bear - Rosewood
Drummond
10.0 out of 10, Exceptional, (2 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 €187
includes taxes & fees
17 May - 18 May
Lundy's Black Bear - Rosewood
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

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 €181 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?

Private Beach and Endless Water : This holiday home rental outside of Ashland is located on a lake, and has an outdoor pool, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Ashland?

With 10 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, Apostle Islands National Lakeshore and Soo Line Locomotive 950 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.