Search Vacation Homes in Ashland

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 165 Vacation Homes in Ashland with updated reviews, rates, and availability.

Home with a beautiful view of Lake Superior and Madeline Island
Interior

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
Winter has returned to Big Snow Country!!
Exterior

Winter has returned to Big Snow Country!!

10.0 out of 10, Exceptional, (13)
"We had a great time and we are already planning for next year "
Winter has returned to Big Snow Country!!
Ontario Suite @ The Bayfield Guest House
Exterior

Ontario Suite @ The Bayfield Guest House

9.4 out of 10, Exceptional, (13)
"Place is very nice and a quick walk to the town, it’s pretty on the outside and was a great place to come back to and grab thing for our hikes or dinner!"
The price is SAR 479
SAR 748 total
includes taxes & fees
22 Mar - 23 Mar
Ontario Suite @ The Bayfield Guest House
Stately home in Washburn
Beach nearby

Stately home in Washburn

9.8 out of 10, Exceptional, (19)
"We had a wonderful stay at the Stately Home. It was very comfortable with a lot of space for my family (6 adults). It provided everything we wanted, spacious kitchen, dining room, huge living room & comfortable bedrooms. Visiting in the winter we didn’t have the opportunity to enjoy the deck & backyard, but are looking forward to staying at the Stately for our 2025 holiday getaway. "
Stately home in Washburn
Sunshine House - Historic Bayfield Farmhouse
Property grounds

Sunshine House - Historic Bayfield Farmhouse

10.0 out of 10, Exceptional, (11)
"Perfect location for a girls weekend away. The Sunshine House was wonderfully equipped and comfortable for us."
Sunshine House - Historic Bayfield Farmhouse
Quiet, peaceful, spotless studio near Lake Superior and all Bayfield amenities.
Interior

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.
Lake Shore Home with private dock and large deck--1 mile from Bayfield
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (94)
"Great property. "
The price is SAR 1,313
SAR 2,521 total
includes taxes & fees
1 Apr - 2 Apr
Lake Shore Home with private dock and large deck--1 mile from Bayfield
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, (20)
"We had a very nice time staying here for the Birkie. Everything was clean and well maintained "
Ride your ATVs and snowmobiles directly from the house!
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Terrace/patio

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 SAR 521
SAR 1,386 total
includes taxes & fees
25 Mar - 26 Mar
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Superior Suite @ The Bayfield Guest House
1 bedroom, desk, free WiFi, bed sheets

Superior Suite @ The Bayfield Guest House

9.6 out of 10, Exceptional, (10)
"We stayed for 2 nights and the unit was exactly as listed. The check in was smooth and we had no issues with the unit. Excellent location made walking to and around the downtown area very easy."
The price is SAR 536
SAR 827 total
includes taxes & fees
24 Mar - 25 Mar
Superior Suite @ The Bayfield Guest House
Huron Suite @ The Bayfield Guest House, Bayfield
Exterior

Huron Suite @ The Bayfield Guest House, Bayfield

9.2 out of 10, Wonderful, (12)
"Very prompt with answering questions. Clean place. "
The price is SAR 479
SAR 748 total
includes taxes & fees
24 Mar - 25 Mar
Huron Suite @ The Bayfield Guest House, Bayfield
Guest House on Owners Lakefront Property
Pool

Guest House on Owners Lakefront Property

10.0 out of 10, Exceptional, (81)
"We really enjoyed our stay on Madeline island! The house was great! We enjoyed time on the beach and were glad for the lift up the hill between the beach and the house. The owners were friendly and helpful. The furniture was clean and comfortable. The appliances all worked well. Things to note: bring your own spices/seasonings. Also, the property is about 20 minutes from the ferry landing (some of which is over a well maintained dirt road). We enjoyed the state and county park as well as local...
Guest House on Owners Lakefront Property
At the end of Bark Point lies your perfect vacation home!
Exterior

At the end of Bark Point lies your perfect vacation home!

9.6 out of 10, Exceptional, (10)
"Beautiful views of Lake Superior.Private, Clean, and well supplied."
At the end of Bark Point lies your perfect vacation home!
Paradise Shores & Fish Galore ~private small beach & dock!
Exterior

Paradise Shores & Fish Galore ~private small beach & dock!

10.0 out of 10, Exceptional, (103)
"Wonderful place - clean, bright, full of everything we needed. The beds were comfortable, kitchen full of everything I needed to cook meals and in a beautiful setting! Thank you for sharing your beautiful home with us! "
Paradise Shores & Fish Galore ~private small beach & dock!
Great Northwoods home with access to all your recreational activities!
Fridge, microwave, oven, stovetop

Great Northwoods home with access to all your recreational activities!

2.0 star property
8.0 out of 10, Very Good, (2)
"Excellent accomodations for a weekend of trail riding"
The price is SAR 788
SAR 1,302 total
includes taxes & fees
22 Mar - 23 Mar
Great Northwoods home with access to all your recreational activities!
Cute cottage on the golf course
Fridge, microwave, oven, stovetop

Cute cottage on the golf course

9.4 out of 10, Exceptional, (61)
"We have stayed multiple times in this cute cottage. It’s great for us (mom, dad, adult daughter). We especially like how it feels like it’s out in the woods but it’s also walking distance to LaPointe! Also there’s plenty of shade & nice golf course views."
Cute cottage on the golf course
Hemlock Chalet @ Brickyard Creek, Bayfield
Beach nearby

Hemlock Chalet @ Brickyard Creek, Bayfield

9.8 out of 10, Exceptional, (7)
"The property is beautiful and nestled into the trees, which made for a gorgeous winter setting. The bedding and bathrobes are luxurious and comfortable. The soaking tub and the fireplace are incredibly relaxing and ensure for a cozy stay. We enjoyed the quiet holiday weekend reading, doing jigsaw puzzles and sipping hot cocoa by the fireplace. We could have easily stayed cozy in the chalet all week, but we were happy to have access to the beautiful scenery nearby for some exercise. It was a...
Hemlock Chalet @ Brickyard Creek, Bayfield
Peaceful Bayfield Getaway: Lake Superior and Madeline Island Views & Sauna
Property grounds

Peaceful Bayfield Getaway: Lake Superior and Madeline Island Views & Sauna

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...
Peaceful Bayfield Getaway: Lake Superior and Madeline Island Views & Sauna
Spring and Summer Openings! Lake Superior Panoramic Views Await!
Interior

Spring and Summer Openings! Lake Superior Panoramic Views Await!

9.8 out of 10, Exceptional, (54)
"We had a great time on the lake, plenty of space for multiple families. Checking in and out was easy."
Spring and Summer Openings! Lake Superior Panoramic Views Await!
300' of Private Beach
Beach nearby, sun loungers

300' of Private Beach

9.0 out of 10, Wonderful, (38)
"Nice beach and property "
300' of Private Beach
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.
Don't see what you're looking for?
See all available properties in Ashland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Ashland

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

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

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.
Mission Springs Resort
One-Bedroom Cottage | View from room

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. "
The price is SAR 481
SAR 606 total
includes taxes & fees
20 Apr - 21 Apr
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.