Ashland Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Ashland holiday rentals

Flat-screen TV, DVD player

Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (73 reviews)
"Love this place! Very cute and right on Lake Superior. Also love the ice cream stocked in the freezer from a local dairy!"
United States
Kimber
The price is HK$1,599
HK$1,687 total
includes taxes & fees
16 Jun - 17 Jun
Mission Springs Resort
TV

South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (23 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
The price is HK$1,246
HK$2,010 total
includes taxes & fees
29 Jun - 30 Jun
South Apartment on Main Street
TV

North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (43 reviews)
"Great location, clean and comfortable. "
United States
Heather Ann M.
The price is HK$1,175
HK$2,043 total
includes taxes & fees
8 Jun - 9 Jun
North Apartment with Lake Superior Views
Exterior

Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!

Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
Mellen
10.0 out of 10, Exceptional, (22 reviews)
"Super clean, super comfortable, perfect peaceful location."
United States
Chris C.
The price is HK$1,716
HK$2,066 total
includes taxes & fees
10 Jun - 11 Jun
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
Property grounds

Great Northwoods home with access to all your recreational activities!

Great Northwoods home with access to all your recreational activities!
Mellen
9.8 out of 10, Exceptional, (14 reviews)
"It is a very spacious home near many fun attractions. Would be great for a friends getaway or fanily vacation. "
United States
Susan
The price is HK$1,567
HK$2,637 total
includes taxes & fees
6 Jul - 7 Jul
Great Northwoods home with access to all your recreational activities!
Property grounds

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

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Bayfield
9.8 out of 10, Exceptional, (235 reviews)
"Great stay and host! "
United States
Jenna Q.
The price is HK$932
HK$1,641 total
includes taxes & fees
30 Jun - 1 Jul
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Beach nearby

Annex No. 1 DePerrys | On Lake Superior Shoreline

Annex No. 1 DePerrys | On Lake Superior Shoreline
Bayfield
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful getaway, The property was perfect for my husband and I. Everything was as advertised."
United States
Sarah S.
The price is HK$1,396
HK$2,161 total
includes taxes & fees
17 Jun - 18 Jun
Annex No. 1 DePerrys | On Lake Superior Shoreline
Fridge, microwave, oven, stovetop

Serenity Now 4BR Lakefront Cabin + Trail Access - Sleeps 12

Serenity Now 4BR Lakefront Cabin + Trail Access - Sleeps 12
Hurley
The price is HK$1,551
HK$3,272 total
includes taxes & fees
18 Jun - 19 Jun
Serenity Now 4BR Lakefront Cabin + Trail Access - Sleeps 12
Iron/ironing board, free WiFi, wheelchair access

Lundy's Black Bear - Rosewood

Lundy's Black Bear - Rosewood
Drummond
10.0 out of 10, Exceptional, (2 reviews)
"Conveniently located for my snowmobile trip and room was very nice and clean. Would definitely stay again."
United States
Curtis E.
The price is HK$776
HK$1,673 total
includes taxes & fees
7 Jun - 8 Jun
Lundy's Black Bear - Rosewood
Beach nearby

The Copper Squirrel is a secluded full log cabin on 10 acres.

The Copper Squirrel is a secluded full log cabin on 10 acres.
Bayfield
10.0 out of 10, Exceptional, (36 reviews)
"Kristin is an amazing host! We are returning guests and loved our stay this time as much as our last time! It’s a cozy cabin with every amenity you could need. We love the location and it’s close to the shops and restaurants we like to visit. We will definitely be returning to this lovely home!"
United States
Lynn P.
The price is HK$1,959
HK$2,744 total
includes taxes & fees
24 Jun - 25 Jun
The Copper Squirrel is a secluded full log cabin on 10 acres.
Exterior

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

The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Bayfield
10.0 out of 10, Exceptional, (35 reviews)
"Fresh air, stars, woodpeckers, saw a bear close by, deer. Awesome!"
United States
Don
The price is HK$1,763
HK$2,504 total
includes taxes & fees
7 Jun - 8 Jun
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Beach

Bayfield Fruit Loop Retreat - Main Cottage

Bayfield Fruit Loop Retreat - Main Cottage
Bayfield
10.0 out of 10, Exceptional, (54 reviews)
"Super close to town and easy to access. We enjoyed our stay!"
United States
Kerry B.
The price is HK$2,292
HK$2,830 total
includes taxes & fees
8 Jun - 9 Jun
Bayfield Fruit Loop Retreat - Main Cottage
Outdoor dining

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge

Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
Cable
10.0 out of 10, Exceptional, (32 reviews)
"Great cabin! Very enjoyable stay and excellent communication. Thank you!"
United States
Edward E.
The price is HK$1,268
HK$2,864 total
includes taxes & fees
9 Jun - 10 Jun
Cozy Lakefront Cabin, Dock + Trails : Trails Lodge
1 bedroom, WiFi, bed sheets

Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (86 reviews)
"Clean room, nice location."
United States
Kyle E.
The price is HK$1,756
HK$2,278 total
includes taxes & fees
7 Jun - 8 Jun
Avenue Side Room at The Copper Trout.
Property grounds

Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2

Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
Upson
10.0 out of 10, Exceptional, (1 review)
"A large group of us rented the Davos Chalet for a long weekend. There was more than enough room for us all. The common area was great for us to eat meals and hang out. The kids loved the game room in the basement. "
United States
Stacy H.
The price is HK$11,282
HK$13,596 total
includes taxes & fees
7 Jun - 8 Jun
Spacious 10-bedroom chalet with WiFi and AC in delightful Upson - Floor 2
TV

Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield

Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
Bayfield
10.0 out of 10, Exceptional, (2 reviews)
"The property is very conveniently located. Easy walk to downtown Bayfield and just 2 blocks from the Madeleine Island ferry dock. The condo is a flat which provides windows on all sides and sunlight all day long, along with a nice view of the lake directly to the east. The condo is also very nicely furnished and the kitchen is fully stocked with everything you would need to cook full meals if you wish to bring your own food. We’re already looking forward to our next trip!"
United States
Shawn W.
The price is HK$1,371
HK$3,063 total
includes taxes & fees
16 Jun - 17 Jun
Ada O’Day Condominium #2 – Lake Superior Views in the Heart of Bayfield
Microwave, oven, stovetop, dishwasher

Up North Oasis - Families & Dogs in the Bayfield Area

Up North Oasis - Families & Dogs in the Bayfield Area
Washburn
10.0 out of 10, Exceptional, (6 reviews)
"Great place to stay! Plenty of amenities and Dog friendly. Would definitely stay here again. "
United States
Susan B.
The price is HK$2,546
HK$4,510 total
includes taxes & fees
16 Jun - 17 Jun
Up North Oasis - Families & Dogs in the Bayfield Area
Iron/ironing board, free WiFi, bed sheets, wheelchair access

Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks
Drummond
10.0 out of 10, Exceptional, (1 review)
The price is HK$776
HK$1,673 total
includes taxes & fees
9 Jun - 10 Jun
Lundy's Black Bear - Blair Oaks
Beach nearby

Annex No. 2 DePerrys | On Lake Superior Shoreline

Annex No. 2 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (24 reviews)
"Very nice place, but you can hear and feel the neighbors in adjacent annex."
United States
Michael
The price is HK$1,396
HK$2,169 total
includes taxes & fees
7 Jun - 8 Jun
Annex No. 2 DePerrys | On Lake Superior Shoreline
Iron/ironing board, free WiFi, bed sheets, wheelchair access

Lundy's Black Bear - Lemgrove

Lundy's Black Bear - Lemgrove
Drummond
The price is HK$776
HK$1,673 total
includes taxes & fees
7 Jun - 8 Jun
Lundy's Black Bear - Lemgrove
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

Legendary Waters Resort & Casino

Legendary Waters Resort & Casino

10/10 Excellent
"Casino was a great place to hang out."
Robert 1-night trip
Posted 2 hours ago
Legendary Waters Resort & Casino

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

  • View our selection of featured holiday rentals in Ashland
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  • Enter your travel dates to view the best deals on holiday rentals in Ashland while they last

Look no further and take a look at our great range of rental properties in Ashland!

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?

Private Beach and Endless Water : This holiday home rental outside of Ashland is located on a lake, and has an outdoor pool, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Ashland?

With 10 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?

Chequamegon Bay 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 Apostle Islands National Lakeshore 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.