Ashland Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Ashland vacation rentals

Flat-screen TV, DVD player

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
$139 nightly
The price is $146
Apr 30 - May 1
Total with taxes and fees
Mission Springs Resort
TV

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
$194 nightly
The price is $213
Apr 30 - May 1
Total with taxes and fees
South Apartment on Main Street
Exterior

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, (18 reviews)
"Super clean, super comfortable, perfect peaceful location."
United States
Chris C.
$205 nightly
The price is $216
Apr 20 - Apr 21
Total with taxes and fees
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
Property grounds

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, (16 reviews)
"Clean, quiet, beautiful private beach! "
United States
Abby K.
$277 nightly
The price is $310
Apr 20 - Apr 21
Total with taxes and fees
All season cottage with sauna overlooking the private beach on Lake Superior
Property grounds

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
$222 nightly
The price is $234
Apr 30 - May 1
Total with taxes and fees
Great Northwoods home with access to all your recreational activities!
TV, fireplace

Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield
Bayfield
10.0 out of 10, Exceptional, (78 reviews)
"Beautiful place!"
United States
Susan S.
$361 nightly
The price is $408
Apr 19 - Apr 20
Total with taxes and fees
Northwoods Chalet @ Brickyard Creek, Bayfield
TV, fireplace

The Snuggery @ Whitecap ~ Ensuite Sauna

The Snuggery @ Whitecap ~ Ensuite Sauna
Upson
9.4 out of 10, Exceptional, (3 reviews)
"Location was great!! The spiral stairs to tje kitchen was a surprise but we made do. "
United States
Leslie O.
$445 nightly
The price is $469
Apr 19 - Apr 20
Total with taxes and fees
The Snuggery @ Whitecap ~ Ensuite Sauna
Interior

Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (59 reviews)
"Great place! Secluded and yet close to town."
United States
Anonymous traveler
$351 nightly
The price is $396
Apr 19 - Apr 20
Total with taxes and fees
Woodland Chalet @ Brickyard Creek, Bayfield
Beach nearby

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.
$232 nightly
The price is $247
May 3 - May 4
Total with taxes and fees
Annex No. 1 DePerrys | On Lake Superior Shoreline
Exterior

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, (32 reviews)
"Awesome accomodations for us and our two dogs! Quiet and secluded location! Perfect!"
United States
Jon M.
$303 nightly
The price is $320
May 14 - May 15
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
1 bedroom, free WiFi, bed sheets

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.
$200 nightly
The price is $230
Apr 19 - Apr 20
Total with taxes and fees
Lower Flat @ Steeple Hill Flats, Bayfield
Beach nearby

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, (31 reviews)
"Cozy and amazing cabin!We absolutely loved staying at this wonderful cabin in the woods! It was very relaxing and exactly where we needed to be. Kristin does a beautiful job decorating and is in tune with having everything that was needed for our stay. She went above and beyond to make sure we enjoyed our visit! I highly recommend staying here and the location is close to all the areas we like to visit!"
United States
Lynn P.
$303 nightly
The price is $320
May 13 - May 14
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
Smart TV, fireplace

Apostle Pines #4 @ Apostle Highlands Golf Course

Apostle Pines #4 @ Apostle Highlands Golf Course
Bayfield
9.8 out of 10, Exceptional, (16 reviews)
"Outstanding property in all ways, highly recommended."
United States
Mark H.
$433 nightly
The price is $489
Apr 19 - Apr 20
Total with taxes and fees
Apostle Pines #4 @ Apostle Highlands Golf Course
Outdoor dining

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
Cable
10.0 out of 10, Exceptional, (31 reviews)
"Everything was perfect! Very clean and cozy. We would definitely stay again."
United States
Kari G.
$336 nightly
The price is $367
May 3 - May 4
Total with taxes and fees
Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
Iron/ironing board, free WiFi, wheelchair access

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.
$196 nightly
The price is $215
Apr 19 - Apr 20
Total with taxes and fees
Lundy's Black Bear - Rosewood
1 bedroom, WiFi, bed sheets

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.
$201 nightly
The price is $229
Apr 19 - Apr 20
Total with taxes and fees
Avenue Side Room at The Copper Trout.
Dining

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.
$543 nightly
The price is $608
Apr 23 - Apr 24
Total with taxes and fees
Lake Shore Home with private dock and large deck--1 mile from Bayfield
Smart TV, fireplace

Carriage House - Chequamegon Bay, Bayfield

Carriage House - Chequamegon Bay, Bayfield
Bayfield
9.0 out of 10, Wonderful, (11 reviews)
"Great location! Nice and clean."
United States
Janet H.
$433 nightly
The price is $489
Apr 19 - Apr 20
Total with taxes and fees
Carriage House - Chequamegon Bay, Bayfield
Microwave, oven, stovetop, dishwasher

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, (4 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.
$308 nightly
The price is $345
Apr 19 - Apr 20
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
TV

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
$286 nightly
The price is $326
Apr 20 - Apr 21
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
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

Best Western The Hotel Chequamegon

Best Western The Hotel Chequamegon

8/10 Good
"Breakfast was very good with a lot of choices."
Suzanne 1-night trip
Posted 16 hours ago
Best Western The Hotel Chequamegon

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $146 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

SUMMER SPECIALS Beautiful lake front, beach and pool table: This vacation home rental outside of Ashland is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Ashland?

With 11 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, Northern Great Lakes Visitor Center and Apostle Islands National Lakeshore 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.