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

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

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

9.4 out of 10, Exceptional, (24)
"It was a very quaint and cozy place to stay that was very relaxing and enjoyable. "
The price is SAR 620
SAR 1,515 total
includes taxes & fees
25 Dec - 26 Dec
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Winter has returned to Big Snow Country!!
Exterior

Winter has returned to Big Snow Country!!

10.0 out of 10, Exceptional, (7)
"House served as exactly as needed house was very clean and had more cook ware and other supplies items than ever expected absolutely enjoyed the sauna especially after a late cold ride beds were comfortable and house was very cozy had plenty of parking for our 40 ft goose neck our group will definitely be back "
The price is SAR 733
SAR 1,336 total
includes taxes & fees
24 Dec - 25 Dec
Winter has returned to Big Snow Country!!
Cozy House (Hurley, WI/Ironwood, MI area)
Exterior

Cozy House (Hurley, WI/Ironwood, MI area)

9.4 out of 10, Exceptional, (31)
"Quiet neighborhood, close to UTV trails, had everything we eere looking for."
Cozy House (Hurley, WI/Ironwood, MI area)
Ride your ATVs and snowmobiles directly from the house!
Exterior

Ride your ATVs and snowmobiles directly from the house!

10.0 out of 10, Exceptional, (18)
"Another wonderful year at this place. Everything you could ever need. Close to our family and right in town. "
Ride your ATVs and snowmobiles directly from the house!
Private & Plush Retreat W Sauna: Big Views of Madeline Island Atop Bayfield
Spacious Living room with Floor-to-ceiling windows for natural lighting

Private & Plush Retreat W Sauna: Big Views of Madeline Island Atop Bayfield

10.0 out of 10, Exceptional, (3)
"We loved this property for its location and space. We started every morning with coffee on the deck, looking at the beautiful leaves and Lake Superior. The kitchen had everything we needed, with modern appliances and plenty of room for the things we bought. It was great to have so many places to hang out, including a screened in porch, living room and basement. The beds were comfortable and towels were soft. Kevin was very responsive, answering my questions and providing restaurant and hiking...
Private & Plush Retreat W Sauna: Big Views of Madeline Island Atop Bayfield
THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL
Multi-Tier Deck just 100 feet from Lake Michele/Lablonde Flowage.

THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL

9.6 out of 10, Exceptional, (22)
"This was a great place to stay. Rooms were nice!"
THE LAKESIDE EAGLE'S NEST NEAR THE TRAIL
Beautiful golf course property with outstanding views and location
Terrace/patio

Beautiful golf course property with outstanding views and location

10.0 out of 10, Exceptional, (71)
"Our family loves Madeline Island and we were looking for a place that was close to everything, yet was quiet and fit all our needs. This place checked all the boxes! This place had everything we needed and more. It was tucked away with a beautiful view of the golf course. It had an ample amount of towels, kitchenware, beds and seating. It was the perfect place to stay. Highly recommend! "
Beautiful golf course property with outstanding views and location
Tiny’s Retirement Home near the trails
Private kitchen

Tiny’s Retirement Home near the trails

9.8 out of 10, Exceptional, (27)
"The cabin worked great for our hunting party."
Tiny’s Retirement Home near the trails
Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland
Exterior

Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland

10.0 out of 10, Exceptional, (1)
"Our family greatly enjoyed several nights at this cozy cottage! It was clean, had lots of lovely amenities, and was close to Ashland, Washburn and Bayfield. When we had a question, Chelsie responded quickly and thoroughly. Would absolutely recommend it for couples and small families. It didn’t quite provide the lake view we hoped for, but perhaps as leaves fall off, there will be a better view!"
Charming 2-bedroom Rustic House with WiFi, AC and a View in Welcoming Ashland
Sunset Bay Lodge.
Outdoor dining

Sunset Bay Lodge.

9.6 out of 10, Exceptional, (53)
"Beautiful home and property right on lake."
Sunset Bay Lodge.
Lake Shore Home with private dock and large deck--1 mile from Bayfield
Only 1 mile from Bayfield and on the lake shore

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
House 2 - Gorgeous A Frame
Exterior

House 2 - Gorgeous A Frame

10.0 out of 10, Exceptional, (17)
"Our overall stay was very comfortable and fun. This A frame cabin is cute on the inside. We loved that there was an area outside to be able to sit and have a bonfire. Would highly recommend this as a place to stay, "
House 2 - Gorgeous A Frame
Enjoy the Great Outdoors and Lake Superior
Ski House 10 Summer

Enjoy the Great Outdoors and Lake Superior

9.8 out of 10, Exceptional, (35)
"House was as described and exactly what we were looking for. Lots of beds, clean and in the right area. Main areas are a little cozy but worked for us and are as listed. Communication with the host was good. Thanks for a nice stay. "
Enjoy the Great Outdoors and Lake Superior
Home with a beautiful view of Lake Superior and Madeline Island
Welcome to Twin maple Cottage!

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. "
The price is SAR 733
SAR 1,531 total
includes taxes & fees
27 Dec - 28 Dec
Home with a beautiful view of Lake Superior and Madeline Island
Lake house
Room

Lake house

9.0 out of 10, Wonderful, (4)
"My fiancé and I had a lovely stay here at the lake house, it was a great and relaxing weekend. We explored Ironwood a bit, went to Lake Superior for agate hunting (no luck but that’s okay). Good proximity to grocery, restaurants, and local attractions. Just had a bit of a struggle getting in the door initially, we thought it was a code-lock door but later found the keys themselves were in the lockbox so that was new for us haha. No issues besides that, great place!"
Lake house
Hunters Home
Exterior

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
In the Middle Of...
Interior

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...
Apostle Pines #4 @ Apostle Highlands Golf Course

Apostle Pines #4 @ Apostle Highlands Golf Course

9.6 out of 10, Exceptional, (7)
"We have stayed here multiple times. We have family in Bayfield, and we love the golf course. Couldn't be more convenient. This condo has it all! Watching the hummingbirds was a treat!"
The price is SAR 785
SAR 1,722 total
includes taxes & fees
31 Dec - 1 January 2025
Apostle Pines #4 @ Apostle Highlands Golf Course
Majestic views, classic charm, lifelong memories.
Exterior

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

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
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.
Exterior

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

10.0 out of 10, Exceptional, (95)
"Wonderful home and property. Excellent for hiking. "
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
North Apartment with Lake Superior Views
Open concept kitchen/living room with Lake Superior Views (1)

North Apartment with Lake Superior Views

10.0 out of 10, Exceptional, (28)
"Cute, well styled apartment with a view of Lake Superior, and a quick trip to downtown. Would stay again!"
North Apartment with Lake Superior Views
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles
Sea Caves, Sand Island

Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles

9.6 out of 10, Exceptional, (194)
"We stayed 2 nights. Very off seasons, not much going on. Bery nice clean place. Didnt realize we had to climb stairs as my husband had had foot surgery but we made it work. which was"
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles
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.