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

Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Ashland vacation rentals

TV

1. South Apartment on Main Street

South Apartment on Main Street
Ashland
9.8 out of 10, Exceptional, (24 reviews)
"Very nice accommodations. Close to downtown area with shops and Bayview park. "
United States
Mark
$200 nightly
The price is $220
Sep 13 - Sep 14
Total with taxes and fees
South Apartment on Main Street
TV

2. North Apartment with Lake Superior Views

North Apartment with Lake Superior Views
Ashland
10.0 out of 10, Exceptional, (45 reviews)
"Great location, clean and comfortable. "
United States
Heather Ann M.
$252 nightly
The price is $278
Sep 9 - Sep 10
Total with taxes and fees
North Apartment with Lake Superior Views
Flat-screen TV, DVD player

3. Mission Springs Resort

Mission Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (76 reviews)
"Cottage 4 was a blend of rustic charm and recent updates. The beds and furniture were comfortable. We were a party of two, but it would have been roomy for four. The hosts’ welcome gift of local ice cream was a bonus. The location worked well for us. It was just off the highway, but quiet; and we had easy drives to explore towns and trails in the area."
United States
Kathleen
$256 nightly
The price is $270
Sep 8 - Sep 9
Total with taxes and fees
Mission Springs Resort
Exterior

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

Historic Main St w/ Lake View | The Flatwater Loft
Ashland
10.0 out of 10, Exceptional, (1 review)
"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!"
United States
Christina N.
Historic Main St w/ Lake View | The Flatwater Loft
Property grounds

5. 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, (252 reviews)
"Wonderful clean and well appointed place!"
United States
Kinda S.
$187 nightly
The price is $209
Aug 23 - Aug 24
Total with taxes and fees
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
Property grounds

6. Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach

Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach
La Pointe
10.0 out of 10, Exceptional, (9 reviews)
"Great location, clean, owners were responsive and helped with any issues. I would stay here again. "
United States
Angela M.
$172 nightly
The price is $195
Sep 12 - Sep 13
Total with taxes and fees
Camp in style with AC/heat, WIFI, on Main Street, 1 block from Joni's beach
1 bedroom, iron/ironing board, WiFi (free), bed sheets

7. Lundy's Black Bear - Blair Oaks

Lundy's Black Bear - Blair Oaks
Drummond
10.0 out of 10, Exceptional, (4 reviews)
"Extremely quiet and peaceful stay! Very nice motel and location."
United States
Tom H.
$216 nightly
The price is $237
Aug 16 - Aug 17
Total with taxes and fees
Lundy's Black Bear - Blair Oaks
Microwave, oven, stovetop, dishwasher

8. 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, (10 reviews)
"We had a wonderful stay and will be coming back here next time we’re in the area. We found some great hikes!"
United States
Joan Q.
$357 nightly
The price is $400
Sep 8 - Sep 9
Total with taxes and fees
Up North Oasis - Families & Dogs in the Bayfield Area
Interior

9. Annex No. 2 DePerrys | On Lake Superior Shoreline

Annex No. 2 DePerrys | On Lake Superior Shoreline
Bayfield
9.8 out of 10, Exceptional, (27 reviews)
"Great stay for two nights. Amazing views and really close to both Bayfield and Meyers beach which we enjoyed! Accommodations were clean and easy check in and out"
United States
Jeffrey P.
$261 nightly
The price is $278
Sep 1 - Sep 2
Total with taxes and fees
Annex No. 2 DePerrys | On Lake Superior Shoreline
Exterior

10. 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, (34 reviews)
"Property was very clean, very nice amenities and accommodations, comfortable bed, centrally located to many areas to explore! Hosts were very resposive and helpful with any questions! "
United States
Scott D.
$246 nightly
The price is $260
Aug 19 - Aug 20
Total with taxes and fees
Northwoods Cabin Getaway – Perfect for Hiking, Waterfalls, UTV/ATV & More!
Dining

11. Cozy 1-bedroom studio in serene Bayfield with AC

Cozy 1-bedroom studio in serene Bayfield with AC
Bayfield
9.6 out of 10, Exceptional, (4 reviews)
"Great place and accurate to listing"
United States
Olivia M.
$345 nightly
The price is $386
Sep 14 - Sep 15
Total with taxes and fees
Cozy 1-bedroom studio in serene Bayfield with AC
Beach towels

12. Upper level, one bedroom, one bath condo, with Lake Superior views.

Upper level, one bedroom, one bath condo, with Lake Superior views.
La Pointe
10.0 out of 10, Exceptional, (61 reviews)
"Great location, great fit for our get away."
United States
Zach L.
$359 nightly
The price is $407
Aug 17 - Aug 18
Total with taxes and fees
Upper level, one bedroom, one bath condo, with Lake Superior views.
1 bedroom, WiFi, bed sheets

13. Avenue Side Room at The Copper Trout.

Avenue Side Room at The Copper Trout.
Bayfield
9.6 out of 10, Exceptional, (91 reviews)
"The room was awesome - all that we needed. Right in town so very walkable. We would definitely stay here again when we are in the area."
United States
Brendon
$256 nightly
The price is $292
Aug 17 - Aug 18
Total with taxes and fees
Avenue Side Room at The Copper Trout.
Property grounds

14. 3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit

3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Washburn
9.0 out of 10, Wonderful, (37 reviews)
"We had a great time! Beautiful home with easy access to all the South Shore has to offer. "
United States
Anastasia Hopkins F.
$534 nightly
The price is $598
Sep 11 - Sep 12
Total with taxes and fees
3+ Bedroom House +SAUNA, Patio, DIRECT Snowmobile Trail Access, & Firepit
Beach nearby

15. 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, (41 reviews)
"Super cute and cozy cabin. Great base camp for waterfall explorations. Kristin was great to work with and even made sure the woodstove was blazing for our arrival. I also loved all the handmade pottery decorating the space. It was too chilly to be outside much but we did see the turtles and had a greeting from a barred owl one evening. "
United States
Peg C.
$330 nightly
The price is $348
Aug 27 - Aug 28
Total with taxes and fees
The Copper Squirrel is a secluded full log cabin on 10 acres.
Exterior

16. 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, (40 reviews)
"Enjoyed our few nights at this lovely home. So many special touches! Really enjoyed the screened in area and lighting fires and having smores around the fire pit."
United States
elizabeth
$330 nightly
The price is $348
Aug 28 - Aug 29
Total with taxes and fees
The Acorn of Little Sand Bay Secluded, Wooded, and Dog Friendly!
Exterior

17. The Little Bodin

The Little Bodin
Bayfield
9.8 out of 10, Exceptional, (59 reviews)
"Great central location in downtown Bayfield. Very clean. Perfect for our family of four’s long weekend in Bayfield."
United States
Andrew
$358 nightly
The price is $408
Aug 30 - Aug 31
Total with taxes and fees
The Little Bodin
Beach

18. Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods

Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods
Bayfield
10.0 out of 10, Exceptional, (48 reviews)
"We had a wonderful stay! The cabin was stocked with anything you would need, vey clean, and excellent accommodations! Would love to stay again next time we visit!"
United States
Stacey L.
$380 nightly
The price is $425
Sep 3 - Sep 4
Total with taxes and fees
Bayfield Fruit Loop Retreat - Rock Garden Cottage in the woods
Smart TV, books

19. Bayfield Island View `Fedora` on Lake Superior

Bayfield Island View `Fedora` on Lake Superior
Bayfield
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay on the water. Id stay here again!!"
United States
kris p.
$438 nightly
The price is $483
Aug 16 - Aug 17
Total with taxes and fees
Bayfield Island View `Fedora` on Lake Superior
1 bedroom, iron/ironing board, WiFi (free), bed sheets

20. Lundy's Black Bear - Lemgrove

Lundy's Black Bear - Lemgrove
Drummond
9.0 out of 10, Wonderful, (4 reviews)
"Newly constructed with only 3 units so very quiet."
United States
Cheryl A.
$216 nightly
The price is $237
Aug 16 - Aug 17
Total with taxes and fees
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

Whitecap Mountains Resort

Whitecap Mountains Resort

8/10 Good
"Nice large room. Restaurant had good food. Pool is large and well maintained. Only pan is surprise $25 fee collected even though we prepaid through Expedia."
Edward 1-night trip
Posted 8 hours ago
Whitecap Mountains Resort

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $209 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Ashland?

Yes, there are vacation rentals in Ashland close to Ashland Mural Walk, or you can select a more secluded option if you want 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's the top vacation rental that Ashland has to offer?

Fantastic building with AC in lovely Ashland: Visitors give good reviews to this Ashland vacation home rental, which has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Ashland?

With 12 Expedia vacation rentals, you're sure 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 vacation rentals like in Ashland?

Vacation rentals are private properties you can stay in for several days or longer in Ashland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for families.