Ashland Vacation Home Rentals from CA $411: Search Top Private Vacation Homes for Rent

A sandy beach with a wooden structure extending into the water.

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Ashland vacation homes

A modern kitchen with a central island, wooden stools, a stainless steel refrigerator, and a ceiling fan.

1. 2BR Lake Superior Stay | Hot Tub + Walk Downtown

Ashland

CA $616 total

includes taxes & fees

Nov 19 - Nov 20

A brick building with a door and potted plants in front.

2. Historic Main St w/ Lake View | The Flatwater Loft

Ashland

"We absolutely loved our stay. Everything about the set up (check-in/out, amenities, house logistics) were extremely clear. Communication with the hosts was easy and they were quick to respond when we had a question. The location and decoration of the space was perfect. We all agreed it was the perfect balance of a well-curated space while still feeling really homey!We can’t recommend this place enough and we will definitely be back next time we’re in Ashland!"

Christina N.

CA $645 total

includes taxes & fees

Nov 30 - Dec 1

A modern kitchen with a central island, stainless steel appliances, and a bar seating area.

3. Up North Oasis - Families & Dogs in the Bayfield Area

Washburn

ben H.

CA $468 total

includes taxes & fees

Nov 29 - Nov 30

A cozy living room with a sofa, a coffee table, a fireplace, and a fan.

4. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

Washburn

vicki A

CA $594 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with a glass table and chairs overlooking a lake.

5. Serenity Now | 4BR Trailside / Lakefront Cabin

Hurley

kim f.

CA $411 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living room with a stone fireplace, a large brown sofa, a television, and a ceiling fan.

6. Apostle Pines #4 @ Apostle Highlands Golf Course

Bayfield

Anonymous traveller

CA $665 total

includes taxes & fees

Nov 16 - Nov 17

A spacious living room with a wooden ceiling, large windows, a dining area, and a television.

7. Carriage House - Chequamegon Bay, Bayfield

Bayfield

Janet H.

CA $697 total

includes taxes & fees

Nov 15 - Nov 16

A round table with a dark tablecloth and a decorative piece on it, surrounded by wooden chairs. A large window offers a view of a body of water and trees.

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

Bayfield

Brian

CA $824 total

includes taxes & fees

Dec 1 - Dec 2

A hotel room with a large bed, a sitting area with a view, and a bathtub.

9. Main @ Hendrickson House

Bayfield

Steven A.

CA $768 total

includes taxes & fees

Nov 15 - Nov 16

A two-story house with a porch, a garage, and a small attached structure.

10. Carriage @ Hendrickson House

Bayfield

Wendy D.

CA $635 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Find vacation rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Days Inn by Wyndham Hurley

10/10 Excellent

"The room and the staff were so excellent! I was extremely pleased to find so many accessible "grab bars" in the tub/shower, and the shower head/water flow was terrific! Because there is remodeling happening at the hotel, I couldn't give a full 5-Star for those areas - lots of traffic in the hall and doors left open on the rooms being improved - however, my stay was wonderful and I will definitely be booking my next stay with the Hurley, WI Days Inn!"

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

10/10 Excellent

"Stayed here for our annual girls trip! Super happy with all the rooms and big living room to gather for the evening! Loved the decor and homey feel. So fun to sit by the lake too! Would definitely recommend this place!"

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews	239
Accommodation	188 Vacation Homes
Lowest Price	CA $411
Highest Price	CA $824

Explore a world of travel with Expedia

Book Vacation Homes in Ashland on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland vacation homes

1. 2BR Lake Superior Stay | Hot Tub + Walk Downtown

2. Historic Main St w/ Lake View | The Flatwater Loft

3. Up North Oasis - Families & Dogs in the Bayfield Area

4. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

5. Serenity Now | 4BR Trailside / Lakefront Cabin

6. Apostle Pines #4 @ Apostle Highlands Golf Course

7. Carriage House - Chequamegon Bay, Bayfield