Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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

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Top guest favourite

Home in Harshaw

5 out of 5 average rating, 5 reviews

Lakefront Home on Big Bearskin

AndreaRating, 5 stars2 months ago

We had such a good time at the Lawry Lodge! This beautiful house was able to accommodate 8 of us comfortably. The kitchen is where people hangout, eat good food, and enjoy each other’s company and this kitchen checked all the boxes. Very well-appointed pantry with all the accessories you’d ever need. The view was stunning! We took a nice winter stroll to a nearby pub for an Old Fashioned with gently falling snow to make it perfect. Ronda was very helpful and quick to respond when needed. Very happy to have found this little slice of heaven and hope to be back again someday.

Top guest favourite

Home in Two Harbors

4.97 out of 5 average rating, 338 reviews

Classic Vintage Log Cabin on Lake Superior

CarsonRating, 5 starstoday

This Two Harbors Airbnb was a serene escape. Stunning lake views and gentle water sounds created a peaceful, relaxing vibe. The cozy, clean home was perfect for unwinding. Gorgeous surroundings made it a great experience. Highly recommend this beautiful cabin.

Top guest favourite

Cabin in Beaver Bay

4.95 out of 5 average rating, 149 reviews

Superior Lakefront Cabin - Beach - Trail Access

AllisonRating, 5 stars3 weeks ago

Excellent stay! The location is ideal for a north shore adventure and the cabin makes a fantastic basecamp. Comfortable, clean, and thoughtful arranged to accommodate outdoor gear, cooking needs, and hang out space. Not to mention the Lake superior view and private waterfront space!

Guest favourite

Loft in Iron River

4.92 out of 5 average rating, 61 reviews

Glass Tree House| 5 Star|Waterfront|Deluxe Escape

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 stars1 month 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!

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 stars4 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!

Guest favourite

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.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Unique stays

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Popular amenities for Ashland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Ashland's top sights

Chequamegon Food Co-Op4 locals recommend

Deep Water Grille5 locals recommend

Black Cat Coffeehouse3 locals recommend

Super One Foods7 locals recommend

Second Street Bistro7 locals recommend

Bay Theater5 locals recommend

Other great vacation rentals in Ashland

Guest favourite

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 favourite

Home in Herbster

4.91 out of 5 average rating, 55 reviews

Modern Home, Hidden Gnomes & Lake Superior Views

BradRating, 5 stars1 month ago

Spacious bedrooms! Very comfortable home in the woods. It's remote so it makes for a great get away from the congestion of a city. And it's modern so you won't miss any of the comforts of home. Make your menu, bring your groceries and take some time to cook, connect and relax.

Superhost

Home in Ontonagon

4.95 out of 5 average rating, 37 reviews

Lakeside Lookout 3 Bedroom Home

AndyRating, 5 stars2 months ago

Great place for a snowmobile trip! Trail is only 1.5 miles down the road. The view of superior was fantastic and the house was a comfortable place to hang out when we weren't riding.

Guest favourite

Chalet in Bessemer

4.96 out of 5 average rating, 112 reviews

Big Chalet with Hot Tub on Big Powderhorn Mountain

AshleyRating, 5 stars1 month ago

We thoroughly enjoyed our stay at the Snow Escape! Beautiful home in a lovely location and the amenities (hot tub, sauna, etc) are top notch. I can’t recommend this place enough and I absolutely would love to return!

Guest favourite

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!

Guest favourite

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.

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Quick stats about vacation rentals in Ashland

Total rentals
30 properties
Nightly prices starting at
$55 CAD 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

Vacation rentals in Ashland

Top-rated vacation rentals in Ashland

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

Destinations to explore