Ashland Holiday Rentals : Search Short-Term Rentals

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Holiday Rentals in Ashland

Situated in a lush environment, this cabin features a pitched roof and a front door, with two windows on the side.

"We had a great time. It was perfect for us and our 2 older kids. Breathtaking view of Lake Superior. Great communication with host. Highly recommend."

includes taxes & fees

27 Jul - 28 Jul

Enjoy a peaceful retreat on the balcony with a pergola, seating area, and potted plants.

"This place was very nice, it had everything we needed for a long weekend. "

Relax in a serene outdoor seating area with a breathtaking view of a frozen lake and snow-covered landscape.

"Wonderful home and property. Excellent for hiking. "

Cozy living room with a comfortable sofa, armchairs, and a fireplace.

"We had a great time, house was perfect for family to all get together at. Very clean, had all we needed, and close to town."

Enjoy cooking in this well-equipped kitchen with a granite countertop, stainless steel appliances, and a microwave, coffee maker, and stove.

"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!"

Enjoy al fresco dining under the RV's spacious awning, complete with a table and chair set.

"The RV is clean, well maintained, and had everything we needed. The yard and outdoor space was great for our family, and kids to run around. Plenty of space, being on the busy road was not a problem. The host is excellent, very responsive and went above and beyond to make sure we had everything we needed. "

includes taxes & fees

23 Jul - 24 Jul

Relax on the sandy shore, where a weathered log and a nearby tree create a serene atmosphere.

"Nice beach and property "

Surrounded by lush greenery, this natural rock formation extends into a serene body of water.

"The property itself was very nice and clean. Location was great too. We did not have access to many of the amenities advertised though. No pool, tennis courts, dvd player or 2nd tv in the bedroom. "

Relax in a cozy living space with a cushioned sofa, matching armchair, and wooden side table.

"It was an awesome vacation, the boat was an unique stay and loved every minute of it. "

Stroll out to the charming balcony with a potted plant and enjoy the peaceful surroundings.

"Ideal walking location, close to restaurants and shops, pier, ferry and cruise. Comfortable bed and loved the heated bathroom floor!"

includes taxes & fees

22 Jul - 23 Jul

Relax on the outdoor deck with a sectional sofa and dining table, surrounded by a railing and string lights.

"was a great place to stay on the island - was central to everything,"

Enjoy the charm of this two-story home with a welcoming front porch and beautifully manicured lawn.

"It was a very very nice place"

includes taxes & fees

22 Jul - 23 Jul

Relax in this serene outdoor seating area with a round table and two comfortable chairs.

"This cute place just south of Bayfield was perfect for a weekend getaway! "

Sit and enjoy the serene atmosphere in this peaceful gazebo, surrounded by tranquil views.

"This place was perfect! I would definitely stay here again. "

includes taxes & fees

23 Jul - 24 Jul

Relax on the deck with Adirondack chairs and a round table, surrounded by a forest view.

"Beautiful clean and well organized cabin! Cabin was well stocked with everything you could need. We greatly enjoyed our stay. If you are looking in the area for a scenic peaceful stay this is the place for you! Thank you for sharing your beautiful property with our family! "

Stairs lead to a room with a bed and window.

"Very nice and cozy cabin. Great fall colors"

Rustic cabin with a traditional log construction and pitched roof, set amidst a well-maintained lawn.

"We had a great time at this cabin. Hosts were amazing, property was clean and very enjoyable, will go back again. "

Relax in this cabin surrounded by a lush forest, featuring a distinctive triangular roof and a large skylight.

"Everything we and our dog could have ever wanted. Perfect peace and quiet with tons of conveniences. This will be our go-to anytime we visit Bayfield County."

includes taxes & fees

29 Jul - 30 Jul

Relax in this serene bedroom with a large bed, flat-screen TV, and microwave.

" Very nice property, the management was great about making sure we were comfortable and taken care of. And what a view!"

includes taxes & fees

23 Jul - 24 Jul

Guests can enjoy access to a serene beach with rocks and pebbles along the shoreline.

"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! "

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Top Ashland Hotel Reviews

Whitecap Mountains Resort

10/10 Excellent

"Nice property, fun to explore a little bit. We also enjoyed our dinner there. "

Harbor's Edge Motel

10/10 Excellent

"Nice and clean little motel located directly across the street from the ferry to Madeline Island. The room we had was small but adequate for our needs. Bathroom has tiny shower; no tub and the sink is in the main room. Hairdryer is provided. Refrigerator and coffee maker also in the room, but had to move coffee maker to another place with an accessible outlet. There is a microwave and ice machine in another building behind the office. We didn’t have a need for either, but it would be a bit of an inconvenience. We are in our 60s and found that it was very easy to walk to the shops and restaurants downtown. We enjoyed our stay and would definitely return to this place and delightful town. Everyone was very friendly and helpful."

Frequently asked questions

Are there holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to Ashland Mural Walk, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the scenic lakeside in Ashland. Make sure you have time to check out the architecture and waterfront during your trip.

What are some of the best holiday rentals that Ashland has to offer?

Cozy remodeled cottage in heart of Ashland/Chequamegon Bay/Lake Superior: This highly rated holiday home rental in Ashland is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Ashland?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Ashland stay.

What’s there to see and do in Ashland?

Apostle Islands National Lakeshore and Lake Superior are a couple of scenic spots to enjoy the outdoors, whereas Ashland Historical Museum is one of the cultural attractions. While here, Northern Great Lakes Visitor Center and Soo Line Locomotive 950 are other places worth a visit.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.

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Holiday Rentals in Ashland

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Holiday Rentals in Ashland

Mission Springs Resort

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

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

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

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

RV Retreat: Steps from Lake Superior with Basswood Island views

Private Beach and Endless Water

Bayfield- Charming Condo, Jumping Off Point to Apostles

A vacation you won't forget, stay on a 35 foot boat!

The Carriage House Sleeps 4. Downtown Bayfield! Walk to everything!

Bell Street Lodging-Suite

The Little Bodin

Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Privacy in the Valhalla Hills near Bayfield/ Lake Superior. On ATV/Snow trails.

Spirit Lodge- Log Cabin with Large front porch

On a 3200 acre lake with 400 ft of frontage. Great fishing kayaking boating fun

The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!

Erie Suite @ The Bayfield Guest House, Bayfield

Beachfront and Lakehouse With All of the Comforts!

Top Ashland Hotel Reviews

Whitecap Mountains Resort

AmericInn by Wyndham Ashland

Legendary Waters Resort & Casino

Harbor's Edge Motel

The Washburn Inn - On the Lake

Seagull Bay Motel

Super 8 by Wyndham Ashland

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

Blue Wave Inn

Frequently asked questions