Are there vacation rentals with a dedicated workspace in Ashland?

Yes! Work meets play with ease at over 10 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.

Are there pet-friendly vacation rentals in Ashland?

Four-legged friends are welcome in Ashland. Choose from more than 10 vacation rentals for guests traveling with pets.

Are there family-friendly house rentals in Ashland?

Ashland has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Do house rentals in Ashland have air conditioning?

Absolutely! We offer over 10 house rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.

How much does it cost to stay in house rentals in Ashland?

Experience the best of Ashland with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do house rentals in Ashland have wifi?

Absolutely! We offer over 10 house rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

Ashland vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Ashland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Superhost

Cottage in Presque Isle

4.71 out of 5 average rating, 7 reviews

Lakefront Cabin #3 The Perch

YamunaRating, 5 stars19 months ago

The stay was perfect for a quiet getaway that we were looking for. The sunrise views were gorgeous. The cabin was very clean. We look forward to coming back again and hopefully for a longer stay. Scott was a great host and very flexible and we appreciated the hospitality.

Guest favorite

Loft in Iron River

4.92 out of 5 average rating, 61 reviews

Waterfront Glass Treehouse. 5* Amenities. Woof!

JeremyRating, 5 stars6 months ago

What an incredible weekend!! Bill was so very welcoming and his is place was amazing!! We enjoyed many libations and were even able to fancy a pontoon ride on beautiful lake. A picturesque setting in the woods with spectacular views and one of the best hosts we have ever experienced!! Thank you for a wonderful weekend!!

Superhost

Home in Beaver Bay

4.9 out of 5 average rating, 107 reviews

Northwoods Luxury on Private Black Sand Beach

ThomasRating, 5 stars3 weeks ago

Place was fantastic. We stayed 3 nights (March, 2025) with four young kids, two adults. Everything is very well communicated/clear (access, entry, garage, rules, etc) everything is known up front (kitchen items, fireplace, etc) Place is big and quiet too. Very clean, updated, cozy, and well lit (also with blackout curtains in all bedrooms) Kitchen is nice with everything you need to cook, including a grill (already had tea, keurig coffee and cups, oil, seasonings, including paper towels, zip locks, detergent, soap, etc) There is everything you need for the beach (chairs, toys, towels). Tons of games, puzzles, and books. But the best of all..... private beach, sauna, tons of firewood, garage, AND a washer/dryer. Fantastic North Shore Location (near Split Rock Lighthouse, Gooseberry Falls, Two Harbors, Tettegouche, etc). It's quiet, it's big, it's got everything you need, it's a great set up and we would proudly recommend this place to any of our family and friends!

Guest favorite

Chalet in Bessemer

4.95 out of 5 average rating, 246 reviews

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

KaitlinRating, 5 stars3 weeks ago

Great chalet! It was clean and well we're greeted with a dog basket with all the essentials (that was super helpful and amazing). The hot tub was lovely, warm, and CLEAN. All of the beds had different firmness and softness so it can accommodate many different preferences. The dishes were clean, which always makes me happy. We had a lovely stay and would definitely recommend this rental to others.

Superhost

Condo in Bessemer

4.9 out of 5 average rating, 10 reviews

Ski In/Out BunkHouse at Black River Basin, Unit #1

KimRating, 5 stars3 months ago

Alexis and Luke are great hosts! They were very proactive in communicating leading up to our arrival and prior to our check out. Instructions for the lockbox, keys and garbage were very clear. We have stayed there before but for first timers, the instructions on how to get to the lodge were very clear also. They always had wood stocked at the entrance for the fireplace which was super nice. Very clean and cozy. It's ideal for skiing in and out at Black River Basin. We love staying at the Bunkhouse and will be back!

Top guest favorite

Cabin in Hayward

4.98 out of 5 average rating, 49 reviews

Charming Cabin right on Round Lk in Richardson Bay

JerryRating, 5 stars6 months ago

It was a wonderful stay at your beautiful cabin! All of your antiques and decorations were amazing, it was like a museum of hunting and fishing items. Very comfy beds and furniture. We felt right at home the entire time! The fireplace really warmed up the cabin and lent a cozy feel. We enjoyed a campfire every day and evening as we took in the lake views. Having Powell's Restaurant such a short walk away was very handy! We look forward to our next visit!

Guest favorite

Cabin in La Pointe

4.86 out of 5 average rating, 232 reviews

7 Pines La Pointe on Madeline Island

CheyenneRating, 5 stars6 months ago

Paul was great. Super friendly. Our kids enjoyed the wooded area, roasting marshmallows on the fire, playing Uno on the deck while listening to music. No TV and WiFi was perfect to disconnect and enjoy hiking and the sandy beaches! Thanks for the great experience.

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What guests are saying

North Coast Escape | Beach Access | Near Downtown

4.89 out of 5 average rating, 36 reviews1 week ago

Absolutely loved our stay at this beachfront gem on Park Point! Easy beach access was a dream, and Marty McFly (our pup!) gave it two paws up for being so dog-friendly. The location was perfect for strolling to Canal Park's restaurants and shops. Highly recommend for a relaxing and convenient Duluth getaway!

Apartment in Park Point

What guests are saying

North Coast Adventurer's Secluded 1000 acre Oasis

5 out of 5 average rating, 22 reviews1 month ago

Steve is an awesome host! We stayed for snowmobiling when snow conditions were not ideal, but he gave us some tips and suggestions that helped us make the most of it! The house is very cozy, with lots of room for parking trucks and trailers. The surroundings are beautiful, we even saw the northern lights right from the front yard, and heard a wolf in the distance. The snowmobile trail is right across the road from the property, too. Beds are comfy, water was hot, and the kitchen had everything we needed. The wood stove is a great touch too! We’ll be back!

Cottage in Ontonagon

What guests are saying

Spring Promo - Minimalist living at its finest !

4.76 out of 5 average rating, 55 reviews2 months ago

I stayed for one night, but would have no problem booking this place again. It was clean, cozy, quiet neighborhood, comfortable bed, and parking is right by the door to the unit. Perfect space for myself. The host was also great! Diane worked with me when I requested an earlier check in time due to personal time constraints. I recommend.

Apartment in Ironwood

What guests are saying

Luxury Log Home with Lakeside Sauna

4.98 out of 5 average rating, 51 reviews1 week ago

We had a fantastic time staying at Kris’s property. From arrival, we had easy entry, plenty of parking and wooden walkways helped with transporting supplies into the beautiful home. Everything was as described in the description and I want to point out the views are amazing on both the main floor and second floor. We had a great time visiting and hope to make a return trip.

Cabin in Two Harbors

What guests are saying

Bay Top Lake House Spacious Lakeshore Home

4.98 out of 5 average rating, 53 reviews6 months ago

We had a wonderful stay in Monica’s lake front home! Pre-arrival communication was so helpful for an easy check-in. The house was spotless, spacious, bed comfortable, good shower, views spectacular! We enjoyed playing the piano and spinning vinyl - an added bonus! The changing leaves were at their peak in northern WI during our stay. Bayfield is a charming town with the nicest people! Thanks for a fabulous stay!

Home in Bayfield

What guests are saying

Hurley: location for all hobbies, holidays, events

4.89 out of 5 average rating, 47 reviews2 months ago

Perfect location. Plenty of parking for our snowmobile trailer. We enjoyed being able to ride our sleds straight from the property to the trail. Convenient location to restaurants/entertainment. We had a little confusion figuring out what unit was ours but the host was helpful and responsive. My only complaint is the bed frames were more wobbly than we are used to. Otherwise our stay was wonderful. We would stay again!

Apartment in Hurley

What guests are saying

Black Dog Lodging

4.95 out of 5 average rating, 20 reviews2 months ago

The cabin was exactly as described and so much more. Anything and everything you could ever need for a stay. Was up for snowmobiling and location was great! Donald went so far above and beyond to make us comfortable. I can't say enough good things about Donald and his wife and their cabin. We will definitely return. This is definitely a lake Superior treasure!!

Home in Ontonagon

What guests are saying

Beautiful Northwoods Cabin on Grand Portage Lake

4.82 out of 5 average rating, 34 reviews7 months ago

Excellent stay again this year - love The Pine Cone and the property. Cabin had everything we needed. we live the fact that there is an aluminum boat included and we just bring a trolling motor and battery for the lake fishing. Beautifully quiet and great place for morning and evening walks - saw deer and great pine needles smell. Will stay again next summer.

Cabin in Mercer

What guests are saying

Gorgeous Beach House on Lake Superior

4.98 out of 5 average rating, 62 reviews4 months ago

This was one of the best Airbnb experiences I’ve ever had. The property is beautiful, with gorgeous views of Lake Superior from multiple rooms, including the huge windows in the living room. The house is clean, comfortable, and truly has everything you could ever need— I think it’s better stocked with kitchenware than my own home. The house is remote enough to be quiet and peaceful, but close enough to town to quickly run and grab something if you need. The house is remarkably wheelchair accessible, with a ramp to enter and a bedroom, bathroom, and walk-in shower on the first floor, which meant we were able to take my disabled mom with us on a wonderful winter getaway. Katie was friendly and responsive to my questions, going above and beyond to make us comfortable. Thank you so much for sharing this special place!

Home in Ashland

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Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Ashland vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Ashland's top sights

Chequamegon Food Co-Op20 locals recommend

Deep Water Grille16 locals recommend

Black Cat Coffeehouse11 locals recommend

Super One Foods7 locals recommend

Ashland Baking Co7 locals recommend

Second Street Bistro7 locals recommend

Other great vacation rentals in Ashland

Guest favorite

Home in Bessemer

5 out of 5 average rating, 9 reviews

Oui Ski Inn: Snowy Summit

NinaRating, 5 stars1 month ago

We loved our stay here! Just a quick walk over to the base of Big Powderhorn, and very comfortable.

Guest favorite

Chalet in Bessemer

4.96 out of 5 average rating, 111 reviews

Big Chalet with Hot Tub on Big Powderhorn Mountain

JamesRating, 5 stars2 months ago

We thoroughly enjoyed our stay. It was perfect for our family ski vacation. Bob's place was comfortable, warm, and clean. We loved the fireplaces and hot tub after our ski days and the kitchen offed ample space for us all (9) to enjoy time together. Bob's place has a great view of Powderhorn Mountain.

Guest favorite

Home in Spooner

4.94 out of 5 average rating, 32 reviews

Sunset Oasis

KaraRating, 5 stars2 months ago

Stayed here as a winter x-country ski getaway with friends. Very cabin-y feeling (in the best way!) Kitchen worked well for us, sauna was hot, and the beds were comfy!

Superhost

Cabin in Danbury

4.75 out of 5 average rating, 8 reviews

Great Bear Getaway

AlieRating, 5 stars7 months ago

Our girls weekend at Hillary’s was lovely! So peaceful and relaxing! We spent hours at the fire pit. We enjoyed the resort amenities. The place was so adorable. We would definitely stay again if we find ourselves in the Danbury area. I really loved that there was a piece of artwork from the owner hanging in the living room. That was a cool touch! Thanks Hillary for a fantastic stay!

Top guest favorite

Cabin in Gurney

5 out of 5 average rating, 67 reviews

Potato River Falls Log Cabin Retreat 130 Acres

AyanRating, 5 stars8 months ago

We loved our weekend stay at the cabin. The views were stunning and the cabin was very cozy and private. Great hosts! they were able to communicate with any questions we had and the hospitality was top tier. I would definitely recommend this stay to friends and family, it was perfect.

Guest favorite

Villa in Bessemer Township

5 out of 5 average rating, 5 reviews

Cozy Ski Lodge Condo I Alpen Villas at Powderhorn

SamanthaRating, 5 stars1 month ago

We absolutely loved our stay! The connivence of the ski in and ski out was amazing. The rooms were a good size. Pillows comfy. We had three children with us that loved the bunk bed bedroom. The hot tub was clean and a perfect way to end the night after skiing. There is a puzzle and an arcade machine available for family fun. We would have loved to see a deck of cards or board game; but generally speaking those are items that can be brought from home. Overall, the cabin was perfect..

Superhost

Cabin in Mellen

5 out of 5 average rating, 3 reviews

Lakeside - Loon's Nest

MikeRating, 5 stars10 months ago

Cozy little cabin in the north woods. Comfortable beds. Nice enclosed patio. Located right on the lake. It has all the amenities you would need for a long weekend. We'll stocked kitchen with all the cookware you would need.

Top guest favorite

Home in Two Harbors

4.95 out of 5 average rating, 99 reviews

Iver's Place

JoelRating, 5 stars2 weeks ago

We enjoyed our stay at Iver’s place very much! The house was very clean and we were so impressed with all the little extras. We took full advantage of the sauna, games, and guide books. This would be such an awesome spot in the summer with the wonderful patio and access to the fire pit. Also, it was a big plus that our dog could join us!

Show all

Quick stats about vacation rentals in Ashland

Total rentals
30 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Ashland?
Yes! Work meets play with ease at over 10 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Ashland?
Four-legged friends are welcome in Ashland. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Ashland?
Ashland has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Ashland have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Ashland?
Experience the best of Ashland with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Ashland have wifi?
Absolutely! We offer over 10 house rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

Ashland vacation rentals

Top-rated vacation rentals in Ashland

North Coast Escape | Beach Access | Near Downtown

North Coast Adventurer's Secluded 1000 acre Oasis

Spring Promo - Minimalist living at its finest !

Hangar House-Near the Clubhouse and Airstrip

Lake front luxury! Hot tub, relax, swim, sun, fun!

Luxury Log Home with Lakeside Sauna

Bay Top Lake House Spacious Lakeshore Home

Hurley: location for all hobbies, holidays, events

Black Dog Lodging

Sunrise Morning Townhome w/Sauna at Big Powderhorn

Beautiful Northwoods Cabin on Grand Portage Lake

Gorgeous Beach House on Lake Superior

Vacation rentals for every style

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Other great vacation rentals in Ashland

Quick stats about vacation rentals in Ashland

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore