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Compare 139 Vacation Homes in Ashland with updated reviews, rates, and availability.

Motisi's Sandy Beach

10.0 out of 10, Exceptional, (65)
"We enjoyed our stay and loved the beautiful location and view of the water. It's a very spacious and can accommodate a family. "
Motisi's Sandy Beach

Home with a beautiful view of Lake Superior and Madeline Island

10.0 out of 10, Exceptional, (56)
"Communication from MaryAnn was excellent. The home was fully furnished. We did not need anything. Great location. Super clean. Loved our stay there. "
Home with a beautiful view of Lake Superior and Madeline Island

Direct Lake Superior Lake Front; Book the Last Few Summer Weeks Available!

9.8 out of 10, Exceptional, (53)
"We had a wonderful time with our whole family over Thanksgiving. The house was spacious with plenty of room to both spend time together and spread out to get a little space. The host was really responsive and helpful. The house did feel a little bit like a maze to start with but was okay once you got use to it."
Direct Lake Superior Lake Front; Book the Last Few Summer Weeks Available!

Lake house

9.4 out of 10, Exceptional, (6)
"Check in at 3 pm, I messaged manager three four times , finally I called by now it’s after 4, she sent door code promptly, and did apologize.It’s all good"
Lake house

Tiny’s Retirement Home near the trails

9.8 out of 10, Exceptional, (31)
"Had a blast at Tiny's. Great location for snowmobiling just off the trail. Very accommodating host, and communication was great. Very nice setup, we'll stay again!!"
Tiny’s Retirement Home near the trails

Lake Shore Home with private dock and large deck--1 mile from Bayfield

10.0 out of 10, Exceptional, (94)
"Great property. "
Lake Shore Home with private dock and large deck--1 mile from Bayfield

Two bedroom cottage near beautiful Herbster beach.

10.0 out of 10, Exceptional, (82)
"Outstanding property. Picturesque. Great outdoor area. Neat and tidy. Comfortable furniture and bedding. Kitchen is well stocked for cooking. Easy to find. Two minutes to Lake Superior. "
Two bedroom cottage near beautiful Herbster beach.

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

9.4 out of 10, Exceptional, (25)
"Fun place to hang out and sauna with friends after cross country skiing in the area. "
The price is AED 411
AED 1,234 total
includes taxes & fees
24 Feb - 25 Feb
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

Get ready for the best-appointed spot to which to escape on Lake Superior’s South Shore!

10.0 out of 10, Exceptional, (19)
"Well maintained property with several amenities. We had a great time with our family & dog. "
Get ready for the best-appointed spot to which to escape on Lake Superior’s South Shore!

300' of Private Beach

9.0 out of 10, Wonderful, (38)
"Nice beach and property "
300' of Private Beach

Spacious 4-bedroom house in charming Montreal across from The Gile Flowage

10.0 out of 10, Exceptional, (1)
"6 adults stayed a few days and snowmobiled. Plenty of parking and right on the trails. Host was responsive and we would absolutely stay again."
Spacious 4-bedroom house in charming Montreal across from The Gile Flowage

Carriage House - Chequamegon Bay, Bayfield

8.8 out of 10, Excellent, (8)
"Nice, clean and perfect cabin in Bayfield. Nice trail for walking nearby. Would recommend!"
The price is AED 687
AED 1,596 total
includes taxes & fees
24 Feb - 25 Feb
Carriage House - Chequamegon Bay, Bayfield

Balsam House in Washburn, Wisconsin

2.0 star property
9.6 out of 10, Exceptional, (7)
"Very much enjoyed our stay. Clean and comfortable, with outstanding responsiveness and support from the facility manager. Would stay again!"
Balsam House in Washburn, Wisconsin

MadPad - Unique Family Home located right on the Golf Course!

8.8 out of 10, Excellent, (3)
"Great weather, nice home, great week Thank you"
MadPad - Unique Family Home located right on the Golf Course!

Grandpa Jim's Cabin - Close to The Gile Flowage/On ATV Route

10.0 out of 10, Exceptional, (14)
"Perfect little get away to unplug in the northwoods. Within driving distance of anything you could need or want to do"
Grandpa Jim's Cabin - Close to The Gile Flowage/On ATV Route

Stolen Oaks - Cottage with All-seasons Porch, located near the Airport!

9.0 out of 10, Wonderful, (8)
"The real issue was that we were unprepared because the listing was misleading. There were no firepits - listing indicated there were 2. Grill was charcoal and the store on the island charged $20! There were no beach towels - only 4 big towels for showering that needed to double as beach towels. No pizza cutter but decorative seashell butter spreaders - seems odd. No extra paper towels. Listing made it seem that there was a master bathroom - nope. There was one main bathroom and a VERY small...
Stolen Oaks - Cottage with All-seasons Porch, located near the Airport!

Upscale Vacation Stay in Bayfield

10.0 out of 10, Exceptional, (17)
"Very nice "
Upscale Vacation Stay in Bayfield

Taylor Lake Point 3 Bedroom Hotel Room by RedAwning

3.0 star property
6.0 out of 10, (1)
"Location was good for our itinerary which included a trip to Bayfield plus some hiking and a day on the UTV trails. Beautiful scenery at the home, but it seems house had a problem with mice that should get fixed. Overall we enjoyed our stay once we accepted we would share the space with some uninvited guests. 😁"
Taylor Lake Point 3 Bedroom Hotel Room by RedAwning

Island Fox - Home nestled in the Woods with Screened-in Porch!

10.0 out of 10, Exceptional, (5)
"Island Fox was a nice home to stay on the island and had everything we needed and was conveniently located. The screened in porch was comfortable to sit and read without the bugs. We even saw a bear! The check in process ended up being very easy however I didn’t get communication on it in advance and no response when I messaged and called on our drive up. All in all a great stay. Thank you for sharing your home."
Island Fox - Home nestled in the Woods with Screened-in Porch!

Active Lakeview Escape

3.5 star property
Active Lakeview Escape
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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Other property types in Ashland

Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.

10.0 out of 10, Exceptional, (96)
"Spent a long weekend ice fishing in the area. The place worked out perfect, plenty of room for vehicles and trailers. The attached garage to thaw out gear was an added bonus. "
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.

River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay.

10.0 out of 10, Exceptional, (95)
"Always great experience when staying here. Everything is always clean. Plenty of room. Kitchen is well stocked with pots and pans needed. Fire house is super cool! Would highly recommend. "
River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay.

Mission Springs Resort

3.0 star property
9.4 out of 10, Exceptional, (53)
"The place was neat, comfortable, and very cozy. I really enjoyed the fireplace and the short walk to the beautiful view of Ashland at the beach area. "
Mission Springs Resort
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.