Holiday Homes in Ashland

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Ashland

Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat
Exterior

Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat

10.0 out of 10, Exceptional, (57)
"There was plenty of room. The cabin was beautiful as was the lake with plenty to do around the area!"
Lake Namakagon Sunrise Cove~Unwind & Reconnect. Private dock, 2 kayaks, row boat
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Terrace/patio

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior

10.0 out of 10, Exceptional, (37)
"This place was very nice, it had everything we needed for a long weekend. "
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Private Beach and Endless Water
Beach nearby, sun-loungers, beach towels

Private Beach and Endless Water

8.8 out of 10, Excellent, (42)
"Very little traffic and very quiet beach. It was early in the year before tourist season but very quiet neighborhood. Would definitely stay here again. House was very clean. "
Private Beach and Endless Water
Michigan Suite @ The Bayfield Guest House
Exterior

Michigan Suite @ The Bayfield Guest House

9.2 out of 10, Wonderful, (25)
"Could use some updates and lights flickered a lot in the bathroom. Liked the comfortable bed and jacuzzi tub."
Michigan Suite @ The Bayfield Guest House
Paradise Shores & Fish Galore ~your own private beach & dock!
Property grounds

Paradise Shores & Fish Galore ~your own private beach & dock!

10.0 out of 10, Exceptional, (112)
"Very nice house great place to stay "
Paradise Shores & Fish Galore ~your own private beach & dock!
Sunshine House | Historic Bayfield Farmhouse
Property grounds

Sunshine House | Historic Bayfield Farmhouse

9.8 out of 10, Exceptional, (13)
"Great place to stay while visiting Bayfield!"
Sunshine House | Historic Bayfield Farmhouse
Newly remodeled lake home ! Steps away from the beautiful pike lake chain
Property grounds

Newly remodeled lake home ! Steps away from the beautiful pike lake chain

10.0 out of 10, Exceptional, (101)
"Couldn't be happier with the home and the hosts."
Newly remodeled lake home ! Steps away from the beautiful pike lake chain
Great place for a Wonderful Northern Wisconsin get away!!
Fridge, microwave, oven, stovetop

Great place for a Wonderful Northern Wisconsin get away!!

9.6 out of 10, Exceptional, (28)
"Close to town made it easy and convenient to pick up food and needed supplies. Cabin was suppled well, shower had good pressure and beds were comfortable. Thank you for the stay!!"
Great place for a Wonderful Northern Wisconsin get away!!
Beachfront and Lakehouse With All of the Comforts!
On the beach

Beachfront and Lakehouse With All of the Comforts!

10.0 out of 10, Exceptional, (23)
"A great place for families (and their pup). Our kids loved exploring the shoreline after a snowstorm-- they collected ice crystals and loved looking across the bay with the binoculars that were provided. A well stocked kitchen for big meals, this was a great stay! "
Beachfront and Lakehouse With All of the Comforts!
Private & Spacious Lake Superior Lakefront Cabin on Bark Point
Exterior

Private & Spacious Lake Superior Lakefront Cabin on Bark Point

10.0 out of 10, Exceptional, (4)
"What a wonderful place to stay! The view and sunsets were incredible. The host was quick to respond. The house was clean and comfy. Great location between Bayfield and Duluth. We stayed there with our two teens and my parents and we all loved it. Would definitely stay again! "
Private & Spacious Lake Superior Lakefront Cabin on Bark Point
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Exterior

Spacious four bedroom house -walking distance to Lake Superior / Washburn shops

9.4 out of 10, Exceptional, (26)
"This home was wonderful! My family of 6 had more than enough room here and everyone had their own space. There was plenty of towels for us to use. The beds were comfy, we all slept great. We ate dinner one night at Patsy's. Definitely recommend eating there, it was delicious, and we could walk there from the house! The grocery store is also within walking distance. The location was perfect! We spent half our time in Ashland, the other half in Bayfield! Washburn is about halfway between the two....
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Huron Suite @ The Bayfield Guest House, Bayfield
Exterior

Huron Suite @ The Bayfield Guest House, Bayfield

9.4 out of 10, Exceptional, (18)
"We enjoyed soo many great things on our 1st visit to Bayfield! The Guest House was a perfect location to everything"
The price is NZ$358
includes taxes & fees
11 Sept - 12 Sept
Huron Suite @ The Bayfield Guest House, Bayfield
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Terrace/patio

Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown

10.0 out of 10, Exceptional, (3)
"This house is a great place to stay. We highly recommend!"
Spacious Walkable in Bayfield!! Lake Views, Steps to Ferry, Marina & Downtown
Erie Suite @ The Bayfield Guest House, Bayfield
1 bedroom, desk, free WiFi, bed sheets

Erie Suite @ The Bayfield Guest House, Bayfield

9.0 out of 10, Wonderful, (14)
" Very nice property, the management was great about making sure we were comfortable and taken care of. And what a view!"
The price is NZ$364
includes taxes & fees
4 Sept - 5 Sept
Erie Suite @ The Bayfield Guest House, Bayfield
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse
Fridge, microwave, oven, stovetop

Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse

8.8 out of 10, Excellent, (5)
The price is NZ$696
includes taxes & fees
24 Aug - 25 Aug
Charming 2-Bedroom Pet-Friendly Home Walkable to Downtown, Murals & Coffeehouse
Lake Superior Log Home, Northern Wisconsin
Exterior

Lake Superior Log Home, Northern Wisconsin

10.0 out of 10, Exceptional, (49)
"Great place to stay. Location was amazing"
Lake Superior Log Home, Northern Wisconsin
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!
Property grounds

Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!

10.0 out of 10, Exceptional, (20)
"As far as a place to disconnect there is not better place! "
Simple Gifts - A Simple Studio Cabin with Lake Superior Acesss across the Street!
Balsam House in Washburn, Wisconsin
Sun-loungers, beach towels

Balsam House in Washburn, Wisconsin

2.0 star property
9.6 out of 10, Exceptional, (14)
"Nice home in quiet location. Beds were super comfy, well stocked kitchen. Close to all the dining options in town. "
Balsam House in Washburn, Wisconsin
Spacious home with EV charging station two miles from Big Bay Town Park.
Property grounds

Spacious home with EV charging station two miles from Big Bay Town Park.

10.0 out of 10, Exceptional, (4)
"We had a great experience. It was a quick driving distance to the big bay town park which makes it very convenient for beach access. Beautiful home with plenty of room for my children to hang out and play. The hosts are very thoughtful and quick to respond. Strongly recommend and will love to come back again. "
Spacious home with EV charging station two miles from Big Bay Town Park.
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
Fridge, microwave, oven, stovetop

Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails

10.0 out of 10, Exceptional, (52)
"Had a great weekend stay, the house was very clean and well kept. The owners have done an excellent job fixing it up. The owners do a great job with communication as well. I'd highly recommend staying here. "
Entire 3BDR Cottage: Explore Bayfield-Apostle Islands-BigTop-Northwoods-trails
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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Top Ashland Hotel Reviews

Blue Wave Inn

Blue Wave Inn

10/10 Excellent
"This was a very unique hotel. Very few rooms and incredible views. The room was ginormous and so cozy. The shower was huge and had two heads! It was an easy check in and check out process. The cafe downstairs was wonderful. We would most definitely stay here again and will recommend to others!"
Jeanette 2-night trip
Posted 20 hours ago
Blue Wave Inn