Ashland Vacation Rentals
List your property
Owner log in
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
1 mi
50 rentals in Ashland.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
River Rock Cottage Is Located On The Shore Of Lake Superior On Chequamegon Bay.
Rental Home
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Relax on the shores of Lake Superior
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
The PERFECT Beachside Getaway
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Adventure Awaits on the Shores of Lake Superior
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
The Homestead
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Whitetail Waters
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
NEW! Ashland Apartment: Walkable & Pet Friendly!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Breathtaking family getaway on the beach (pet friendly!)
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Save time - get the best Ashland rentals sent straight to your email!
Escape to this private retreat with panoramic views of Lake Superior
Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Farmstead Retreat with woods, pond, trails and easy access to local attractions
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Madeline Island Lakeside Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Cozy Cabin with Majestic View, Close to Town
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Lake Superior Beachfront, 4+ Bedrooms, Spectacular Timberframe Home
Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
Gorgeous Chalet on Lake Superior with Private Sandy Beach!
Rental Home
4 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
More info
Check in
Check out
Bell Street-Downtown Oasis
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Beautiful home on the golf course on Madeline island 3 bedrooms 8 beds
Rental Home
3 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Valley Vista- 3 Bed Cabin in Valhalla Hills. 2 NIGHT MINIMUM WINTER SPECIAL
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Luxurious Lake Superior Estate with Outdoor Hot Tub
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Entire Cozy Cottage on Bayfield Peninsula
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Cute cottage on the golf course
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Salmo House - Salmo Retreat
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Washburn Beach House Sleeps 6, Private Beach, 11.6 Miles from Bayfield!
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Eagle Moon - Unique 8 sided Home Nestled in the Woods Pet Friendly!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
7 Pines LaPointe On Madeline Island
Cabin
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Payne Cottage - Unique Private Lake Access Home with a Loft
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Parkside Condo 6 - 2 Bedrooms 2 Baths
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Salmo Studio - Salmo Retreat
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Spacious four bedroom house -walking distance to Lake Superior / Washburn shops
Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Cedar Log Cabin - Wonderful Family Cabin located on the Robert Trent Jones Golf
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Unique Family Home on Golf Course
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Cozy Pines Cabin - Wonderful Sunsets and Lake Superior Access!
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Lakefront Condo A Few Steps to Lake Superior
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Yoga & Vacation in Bayfield County WI
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Parkside Condo 7 - 2 Bedrooms 2.5 Baths
Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Sunset View - 3 Bedroom 2.5 Home with Guest House
Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Remodeled Downtown Condo
Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Quaint updated apartment overlooking the Bay
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Updated Suite in great location close to Bayfield, the Apostle Islands, and more
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Peaceful 3+ Bedroom Home w/ SAUNA, Big Field/firepit, Ravine Garden Patio,
Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Slainte - 3 Bedroom 3 Bathroom Cottage
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
La Sirena - 2 Bedroom 2 Bath Cottage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Quaint updated apartment overlooking the Bay
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Bayfield Farmhouse Sleeps 16 - 4 bdrm/2 baths king
Rental Home
5 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Stately Home in Washburn WI. Walking distance to Chequamegon Bay, Lake Superior
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Comfortable suite, great location, easy access to Lake Superior!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
The Boathouse Lodge on Madeline Island
Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Newly Renovated House on Lake Superior with Private Beach
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Spacious townhome on Madeline Island Golf Course
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
1
Frequently Asked Questions about Ashland
- Yes, here are some popular vacation rentals in Ashland that have a pool:\n
- \n
- The Homestead \n
- The PERFECT Beachside Getaway \n
- Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails. \n
- Yes, here are some popular vacation rentals in Ashland that have internet access:\n
- \n
- The Homestead \n
- The PERFECT Beachside Getaway \n
- Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails. \n
- The best pet friendly rentals in Ashland are:\n\nSee all pet friendly vacation rentals in Ashland on Tripadvisor
- Some of the most popular kid friendly rentals in Ashland are:\n
- \n
- The PERFECT Beachside Getaway \n
- Gateway to Lake Superior-near Ashland, WI . Private Cabin-237 acres & Trails. \n
- Adventure Awaits on the Shores of Lake Superior \n