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Holiday rentals in Ashland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Ashland

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

Guest favourite

Cabin in Ironwood

4.95 out of 5 average rating, 407 reviews

The Shell Cabin at Rockhound Hideaway

An outdoor enthusiasts dream awaits at Rockhound Hideaway's Shell Cabin, with opportunities for snowshoeing, skiing, hiking, fishing and everything in between. Take in the views from your back deck, relax around the bonfire, enjoy walk to Lake Superior, hike or snowshoes the North Country Trail to waterfalls or take a day trip to the Porkies. Don't forget to visit Downtown Ironwood and experience its charm for yourself. Amazing star gazing and Northern Lights potential! 420 Friendly for 21&up.

19–26 Aug

₹7,803 per night
Superhost

Apartment in Bayfield

4.81 out of 5 average rating, 255 reviews

One Minute Walk to Lake Superior. Brookside #3

Amazing location! No cleaning fee! This Condo sleeps 4, King bed & Queen sofa sleeper. Full kitchen, balcony, AC, CableTV, WiFi, BBQ, fire pit, and bikes. Restaurant, bar and pool in July-Sept.Bayfield is a 2.3 mile hike or bike on the Brownstone Trail. Brookside is 5 minutes from Mt Ashwabay, Big Top, Bayview beach and multiple hiking trails. Ride a ferry ride to Madeline or cruise the Apostles. Sail, fish, kayak, golf, ski. Pool opens in July. $40 pet fee per stay. 🙂 No smoking allowed.

4–11 May

₹9,416 per night
Guest favourite

Cabin in Iron River

4.95 out of 5 average rating, 123 reviews

Log Cabin at Spider Lake

Step back in time in an authentic seventy year old hand hewn log cabin located on a northern Wisconsin lake with no public access. The cabin has all modern amenities. Rental includes two kayaks, a canoe, a 14 foot fishing boat, and two bicycles. The cabin sits of 1.5 wooded acres with 300 ft. of lake frontage. There is no WIFI in the cabin. WIFI is available 3 miles away at the Iron River library 24/7. The cabin has cell service. Nightly rate includes state and local occupancy tax

27 Nov – 4 Dec

₹13,417 per night

Popular amenities for Ashland holiday rentals

Stay near Ashland's top sights

Deep Water Grille16 locals recommend
El Dorado3 locals recommend
Frankie's Pizza4 locals recommend
Super One Foods7 locals recommend
Prentice Park3 locals recommend
Black Cat Coffeehouse11 locals recommend

Other great holiday rentals in Ashland

Guest favourite

Home in Ashland

4.87 out of 5 average rating, 208 reviews

Entire- Cozy Chequamegon Home

5–12 Sep

₹14,292 per night
Guest favourite

Tiny home in Lake Nebagamon

4.97 out of 5 average rating, 348 reviews

Berrywood Acres Cabin

13–20 Sep

₹11,439 per night
Guest favourite

Cabin in Herbster

4.94 out of 5 average rating, 137 reviews

SOUTH SHORE A-FRAME//Steps from Lake Superior

18–25 Apr

₹14,424 per night
Guest favourite

Cabin in Washburn

4.95 out of 5 average rating, 178 reviews

The Long House

22–29 Mar

₹11,252 per night
Guest favourite

Cabin in Solon Springs

4.97 out of 5 average rating, 148 reviews

Valley Red Cabin

6–13 May

₹9,793 per night
Superhost

Apartment in Ashland

4.91 out of 5 average rating, 65 reviews

Main Street apt 2 blocks from Lake Superior!

10–17 May

₹9,867 per night
Guest favourite

Home in Ashland

4.84 out of 5 average rating, 69 reviews

The MacArthur House

8–15 Apr

₹10,316 per night
Guest favourite

Holiday home in Washburn

5.0 out of 5 average rating, 28 reviews

Historic Hawkes Apartment

13–20 Mar

₹10,818 per night
Guest favourite

Home in Ashland

5.0 out of 5 average rating, 24 reviews

6 blocks to Lake Superior/Bay - Old World Charm

16–23 Jun

₹16,048 per night
Superhost

Home in Ashland

4.8 out of 5 average rating, 54 reviews

South Superior Escape

27 Oct – 3 Nov

₹14,057 per night
Guest favourite

Bungalow in Ashland

4.93 out of 5 average rating, 45 reviews

Ashland Green Bungalow: Vintage Style w/ lake view

11–18 Sep

₹16,788 per night
Guest favourite

Cabin in Washburn

4.94 out of 5 average rating, 16 reviews

Snowmobile, Ski, or ATV Direct from This Cozy Cabi

8–15 Apr

₹6,719 per night

Quick stats about holiday rentals in Ashland

Total rentals

30 properties

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.6T reviews

Nightly prices starting at

₹3,334 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Ashland County
  5. Ashland