Ashland Vacation Rentals

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Check prices for these dates

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Ashland vacation rentals

Interior
North Apartment with Lake Superior Views

North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (42)
"We loved our stay! It was a beautiful place and so comfortable."
United States
Jennifer S.
$180 nightly
The price is $196
Dec 28 - Dec 29
Total with taxes and fees
North Apartment with Lake Superior Views
Fridge, microwave, oven, stovetop
A Cozy Getaway in Ashland

A Cozy Getaway in Ashland

A Cozy Getaway in Ashland
Ashland
10.0 out of 10, Exceptional, (14)
"Great place and host"
United States
Dustin W.
$215 nightly
The price is $241
Jan 5 - Jan 6, 2026
Total with taxes and fees
A Cozy Getaway in Ashland
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

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Bayfield
9.8 out of 10, Exceptional, (229)
"Location was perfect!"
United States
amy g.
$154 nightly
The price is $173
Dec 28 - Dec 29
Total with taxes and fees
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Exterior
The Copper Squirrel is a secluded full log cabin on 10 acres.

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, (27)
"Perfect little cabin. So easy to kick back and relax and with local attractions being just 15-20 min away the location was perfect. Clean cabin, very responsive and kind host. Would 100% recommend to anyone looking to explore the beautiful Bayfield area."
United States
Lance K.
$226 nightly
The price is $238
Jan 18 - Jan 19, 2026
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
Exterior
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

Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
2.0 star property
Upson
10.0 out of 10, Exceptional, (1)
"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.
$1,617 nightly
The price is $1,706
Dec 27 - Dec 28
Total with taxes and fees
Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
Fridge, microwave, oven, stovetop
Brookside Hide-A-Way #2, Port Superior, Bayfield

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

Brookside Hide-A-Way #2, Port Superior, Bayfield
Bayfield
9.6 out of 10, Exceptional, (35)
"Clean, well organized cabin, great Decor!"
United States
kathy m.
$200 nightly
The price is $225
Dec 31 - Jan 1, 2026
Total with taxes and fees
Brookside Hide-A-Way #2, Port Superior, Bayfield
Exterior
Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield

Northwoods Chalet @ Brickyard Creek, Bayfield
Bayfield
10.0 out of 10, Exceptional, (76)
"It was perfect. Clean, cozy. Great get away for the wife and me "
United States
Bill R.
$349 nightly
The price is $394
Jan 7 - Jan 8, 2026
Total with taxes and fees
Northwoods Chalet @ Brickyard Creek, Bayfield
TV
Modern Cabin on a River Bluff

Modern Cabin on a River Bluff

Modern Cabin on a River Bluff
Mason
9.8 out of 10, Exceptional, (16)
"Very clean home in a private area! We did a lot of UTV riding and thus property was centrally located to me all of our needs. "
United States
Janet K.
$142 nightly
The price is $150
Jan 12 - Jan 13, 2026
Total with taxes and fees
Modern Cabin on a River Bluff
Iron/ironing board, free WiFi, bed sheets, wheelchair access
Lundy's Black Bear - Lemgrove

Lundy's Black Bear - Lemgrove

Lundy's Black Bear - Lemgrove
2.0 star property
Drummond
$174 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lundy's Black Bear - Lemgrove
Interior
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!

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, (17)
"Super clean, super comfortable, perfect peaceful location."
United States
Chris C.
$245 nightly
The price is $258
Dec 29 - Dec 30
Total with taxes and fees
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
Outdoor dining
Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield

Woodland Chalet @ Brickyard Creek, Bayfield
Bayfield
9.8 out of 10, Exceptional, (58)
"Exceeded expectations! The best of both worlds. Rustic, but with all of the amenities you could want. Perfectly private and secluded yet very close to Bayfield. Clean, fresh, and breezy. We loved the fully equipped kitchen, and the screened-in deck. There was no need to eat out. Online check in was easy, and we were able to get help via text when we needed extra towels and when we had a question about the TV. "
United States
Wendy L.
$339 nightly
The price is $383
Jan 6 - Jan 7, 2026
Total with taxes and fees
Woodland Chalet @ Brickyard Creek, Bayfield
Beach
Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (52)
"The cabin is extremely clean and well organized with anything you can think of. It's located really close to town, but just outside, so you have peace and quiet. The hosts are very responsive and it made for a perfect trip. "
United States
Matthew
$286 nightly
The price is $320
Dec 30 - Dec 31
Total with taxes and fees
Bayfield Fruit Loop Retreat - Main Cottage
1 bedroom, WiFi, bed sheets
Lake Side Room at The Copper Trout.

Lake Side Room at The Copper Trout.

Lake Side Room at The Copper Trout.
Bayfield
9.2 out of 10, Wonderful, (100)
"Great location and exactly what we needed for our two night stay in Bayfield. Everything in town was walkable from the VRBO as well. Would stay again!"
United States
Alexander L.
$202 nightly
The price is $230
Dec 26 - Dec 27
Total with taxes and fees
Lake Side Room at The Copper Trout.
Microwave, oven, stovetop, dishwasher
Up North Oasis - Families & Dogs in the Bayfield Area

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, (1)
$289 nightly
The price is $324
Jan 4 - Jan 5, 2026
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
Smart TV, fireplace
Apostle Pines #4 @ Apostle Highlands Golf Course

Apostle Pines #4 @ Apostle Highlands Golf Course

Apostle Pines #4 @ Apostle Highlands Golf Course
Bayfield
9.6 out of 10, Exceptional, (15)
"Very clean, relaxing and beautiful location! "
United States
Garry H.
$420 nightly
The price is $474
Jan 4 - Jan 5, 2026
Total with taxes and fees
Apostle Pines #4 @ Apostle Highlands Golf Course
Fridge, microwave, oven, stovetop
Carriage House - Chequamegon Bay, Bayfield

Carriage House - Chequamegon Bay, Bayfield

Carriage House - Chequamegon Bay, Bayfield
Bayfield
9.0 out of 10, Wonderful, (11)
"This is a nice home nestled in a beautiful wooded area. Very clean and comfortable, nice attention to detail. It’s in close proximity to Bayfield, which is a hidden gem of the Great Lakes area. We’ve been to 49 states, and this area is one of our favorites."
United States
Matt
$406 nightly
The price is $458
Dec 26 - Dec 27
Total with taxes and fees
Carriage House - Chequamegon Bay, Bayfield
Iron/ironing board, free WiFi, wheelchair access
Lundy's Black Bear - Rosewood

Lundy's Black Bear - Rosewood

Lundy's Black Bear - Rosewood
2.0 star property
Drummond
$174 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lundy's Black Bear - Rosewood
Interior
Outer Island Apartment @ The Copper Crown

Outer Island Apartment @ The Copper Crown

Outer Island Apartment @ The Copper Crown
Bayfield
9.8 out of 10, Exceptional, (8)
"The home looks as pictured and is settled up on a hill with great sight lines over the town and Lake Superior. My daughter and I didn’t mind the extra muscle burn walking up/down hill to walk the shops or grab a bit to eat. The location was an easy drive to park if desired downtown or head to Washburn for dinner. The room had all necessities for the kitchen, bathroom, shower, and cozy bed after kayaking and hiking. Thanks for a great stay! "
United States
Erin W.
$288 nightly
The price is $330
Dec 26 - Dec 27
Total with taxes and fees
Outer Island Apartment @ The Copper Crown
Iron/ironing board, free WiFi, bed sheets, wheelchair access
Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks
2.0 star property
Drummond
$197 nightly
The price is $216
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lundy's Black Bear - Blair Oaks
Fridge, microwave, oven, stovetop
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

Lake Shore Home with private dock and large deck--1 mile from Bayfield
Bayfield
10.0 out of 10, Exceptional, (111)
"Beautiful views, great location and proximity to Bayfield. Loved our stay. Will be back in the fall! "
United States
Monica O.
$686 nightly
The price is $768
Dec 31 - Jan 1, 2026
Total with taxes and fees
Lake Shore Home with private dock and large deck--1 mile from 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

Whitecap Mountains Resort

Whitecap Mountains Resort

10/10 Excellent
"Hot tub wax excellent after a day of skiing. It was nice having the lodging the bar the ski tickets the pool, hot tub right on site. Ski in/ski out."
Julie 2-night trip
Posted 4 days ago
Whitecap Mountains Resort

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 $179 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?

Downtown Bayfield Home W/ Lake Views, Steps to Ferry & Marina: This vacation home rental outside of Ashland is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Ashland?

With 9 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, Ashland Mural Walk and Northern Great Lakes Visitor Center 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.