Ashland Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

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
$207 nightly
The price is $219
May 26 - May 27
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
$192 nightly
The price is $211
May 3 - May 4
Total with taxes and fees
South Apartment on Main Street
Property grounds

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.
$1,631 nightly
The price is $1,721
May 3 - May 4
Total with taxes and fees
Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
1 bedroom, WiFi, bed sheets

Lake Side Room at The Copper Trout.

Lake Side Room at The Copper Trout.
Bayfield
9.2 out of 10, Wonderful, (100 reviews)
"Room was clean and in a great location for enjoying the greater Bayfield area."
United States
Sally R.
$253 nightly
The price is $289
May 3 - May 4
Total with taxes and fees
Lake Side Room at The Copper Trout.
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, (19 reviews)
"Super clean, super comfortable, perfect peaceful location."
United States
Chris C.
$204 nightly
The price is $215
May 4 - May 5
Total with taxes and fees
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
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
May 10 - May 11
Total with taxes and fees
Lake Shore Home with private dock and large deck--1 mile from Bayfield
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.
$317 nightly
The price is $347
May 3 - May 4
Total with taxes and fees
Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
Property grounds

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, (232 reviews)
"Great stay and host! "
United States
Jenna Q.
$151 nightly
The price is $169
May 26 - May 27
Total with taxes and fees
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
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, (33 reviews)
"Awesome accomodations for us and our two dogs! Quiet and secluded location! Perfect!"
United States
Jon M.
$277 nightly
The price is $292
May 14 - May 15
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Exterior

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.
$534 nightly
The price is $598
May 25 - May 26
Total with taxes and fees
Bayfield Fruit Loop Retreat -2 Cottages
Beach nearby

Annex No. 2 DePerrys | On Lake Superior Shoreline

Annex No. 2 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (22 reviews)
"Great stay for two nights. Amazing views and really close to both Bayfield and Meyers beach which we enjoyed! Accommodations were clean and easy check in and out"
United States
Jeffrey P.
$232 nightly
The price is $247
May 3 - May 4
Total with taxes and fees
Annex No. 2 DePerrys | On Lake Superior Shoreline
Fridge, microwave, oven, stovetop

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.
$252 nightly
The price is $284
May 31 - Jun 1
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
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, (17 reviews)
"The lakefront property has breathtaking views of south shore "
United States
BRIAN
$326 nightly
The price is $365
May 3 - May 4
Total with taxes and fees
All season cottage with sauna overlooking the private beach on Lake Superior
Smart TV, fireplace

Young’s Northwoods Rental

Young’s Northwoods Rental
Mellen
$254 nightly
The price is $268
May 3 - May 4
Total with taxes and fees
Young’s Northwoods Rental
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, (32 reviews)
"Everything was amazing. The host gave us great travel and food references. The cabin is only a short drive to Bayfield and the ferry to Madeline Island. The cabin was a perfect central location for us to drive to our different hikes in the area we had picked out prematurely. Cannot recommend this place enough. "
United States
Johnathan S.
$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.
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
$224 nightly
The price is $236
May 4 - May 5
Total with taxes and fees
Great Northwoods home with access to all your recreational activities!
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
$429 nightly
The price is $489
May 3 - May 4
Total with taxes and fees
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
Outdoor dining

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.
$332 nightly
The price is $381
May 7 - May 8
Total with taxes and fees
Outer Island Apartment @ The Copper Crown
Exterior

Upper Flat @ Steeple Hill Flats, Bayfield

Upper Flat @ Steeple Hill Flats, Bayfield
Bayfield
8.8 out of 10, Excellent, (13 reviews)
"Great views of Superior and comfortable stay"
United States
Josh F.
$263 nightly
The price is $302
May 3 - May 4
Total with taxes and fees
Upper Flat @ Steeple Hill Flats, 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.
$325 nightly
The price is $364
May 3 - May 4
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
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

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

10/10 Excellent
"Clean room"
Roger 1-night trip
Posted 1 day ago
Days Inn by Wyndham Hurley

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 $169 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?

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

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, Apostle Islands National Lakeshore and Soo Line Locomotive 950 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.