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Compare 160 Vacation Homes in Ashland with updated reviews, rates, and availability.

300' of Private Beach
9.0 out of 10, Wonderful, (37)
"Nice beach and property "
300' of Private Beach
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
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
9.8 out of 10, Exceptional, (47)
"We loved the decor and the beds and furniture were super comfortable!"
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
10.0 out of 10, Exceptional, (35)
"I would absolutely stay here again! It was so beautiful and they have thought of every detail to ALL age groups! The weather was a little gloomy, rainy and cold while we were there but it didn’t matter because we knew we had a safe warm place to come home too! The first night we got there we enjoyed the outdoor area with our kids. We played games and had a little fire going in the fire table! It was much needed family time and we were so blessed to be able to have that at this home! Don’t pass...
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
9.2 out of 10, Wonderful, (22)
"We stayed for a family weekend with our adult son. Loved the proximity to hiking trails and restaurants & brewery in Washburn. The place isn't fancy, but was perfect for us. We enjoyed the sauna and campfires outside."
The price is SAR 695
SAR 1,603 total
includes taxes & fees
14 Nov - 15 Nov
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
SUMMER SPECIALS Beautiful lake front, beach and pool table
9.8 out of 10, Exceptional, (15)
"We had a great time staying at this location. The fall weather was nice and cool and the scenery was beautiful. The house was very nice and clean with lots of rooms and things to do. Would reccommend!"
SUMMER SPECIALS Beautiful lake front, beach and pool table
Lake Shore Home with private dock and large deck--1 mile from Bayfield
10.0 out of 10, Exceptional, (93)
"Monica has a beautiful home right on Lake Superior. There was everything we needed to make family meals. The beds were very comfy,and the home was immaculate. Would highly recommend this property!"
Lake Shore Home with private dock and large deck--1 mile from Bayfield
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.
10.0 out of 10, Exceptional, (6)
"Beautiful property in a quiet area with a 35 minute easy drive to Bayfield. Near Myers’s Beach which has an absolutely stunning bluff hike. "
This house is a 2 bedroom(s), 2 bathrooms, located in Herbster, WI.
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
10.0 out of 10, Exceptional, (22)
"We had a fantastic time at the Lenawee Getaway! The backyard games and fire pit were so fun for our family and had a blast playing the games. This was the getaway our family needed. We had fun exploring Herbster and the fun shops/establishments in town! Great food and very friendly people! Thank you!"
This cozy cottage is a short walk to Herbster beach! Easy access to TRAILS!
Tiny’s Retirement Home near the trails
9.8 out of 10, Exceptional, (26)
"Very impressive overall give it a 10 plan on staying there again"
Tiny’s Retirement Home near the trails
Majestic views, classic charm, lifelong memories.
10.0 out of 10, Exceptional, (37)
"Sweet little spot nestled on the edge of the lake - loons, eagles, the lapping of water on the shore, blue sky and pine trees. Everything a couple of city-dwellers needs to decompress and unwind. Great location to explore the woods in the area - mountain biking trails and unique dining experiences nearby. Highly recommend a trip to Delta Diner, we loved it. Chris was a true pleasure to chat with, he couldn't have been more accommodating helping us get situated. Cabin is comfy and has a great...
Majestic views, classic charm, lifelong memories.
Still Life Cottage @ Brickyard Creek, Still Life Cottage @ Brickyard
9.2 out of 10, Wonderful, (10)
"We enjoyed the art-filled cabin. It was very clean and comfortable. Beautiful area too! "
Still Life Cottage @ Brickyard Creek, Still Life Cottage @ Brickyard
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!
Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!
9.8 out of 10, Exceptional, (42)
"Loved everything about this place! We had a great time and we will be back! "
Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!
Hunters Home
9.8 out of 10, Exceptional, (63)
"This is our second time staying at this property and like my title says, it just keeps getting better the more you come. This time, we added to our crew and brought my parents with. They loved the place. Our girls could not get over how many toys they had to play with and how much space they had to run and play in and on the property. Thank you for sharing your wonderful cabin with us. We’ll be back again!"
Hunters Home
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home
10.0 out of 10, Exceptional, (121)
"The pictures don’t do this place justice! We had an amazing time with friends and family. Our hosts were unbelievably communicative - and they made our stay as easy and comfortable as could be. Halfway through the trip, our party discussed making this an annual rental! 5 stars!"
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home
In the Middle Of...
9.8 out of 10, Exceptional, (18)
"The house and the property were very clean and nicely kept. The views were great, wildlife everywhere! We really enjoyed the amount of bedrooms and space. We didnt have a single complaint! Very nice!"
In the Middle Of...
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the
10.0 out of 10, Exceptional, (18)
"Watch sunrise each day, follow critter tracks on the beach, breathe in the pine aroma and relax. Top tip: the electric heater has a remote—no one has to get out of bed to turn it on in the morning! Neat and tidy with the essentials. We loved it."
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the
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!
Entire Home Near Lake Superior
10.0 out of 10, Exceptional, (15)
"Great time thanks!!!"
Entire Home Near Lake Superior
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, (94)
"Did job up there! My wife loved house and area. I worked pretty much whole time. But Saturday afternoon and Sunday morning where very nice"
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
North Apartment with Lake Superior Views
10.0 out of 10, Exceptional, (27)
"Cute, well styled apartment with a view of Lake Superior, and a quick trip to downtown. Would stay again!"
The price is SAR 470
SAR 850 total
includes taxes & fees
1 Dec - 2 Dec
North Apartment with Lake Superior Views
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
9.6 out of 10, Exceptional, (185)
"Fabulous location and beautiful condo "
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
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.