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Ashland vacation rentals

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Top-rated vacation rentals in Ashland

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Home in Ashland

4.87 out of 5 average rating, 229 reviews

Entire- Cozy Chequamegon Home

Escape suburbia at our quaint farm style house about a mile from Lake Superior and about 1/2 mile from Northland College. Guests describe our home as cozy & reminiscent of visiting their favorite coffee shop. The house offers 4 bedrooms, 1 full bathroom on the second floor & a half bath on the main floor. A portable crib is available for infants (30 1b max). Please note that we are in the process of having baseboards milled by a local crafts person who is also installing them when we are closed.

Guesthouse in Sayner

4.98 out of 5 average rating, 177 reviews

Sauna Snowshoe&Pinely Peace-Lands End at Edge Loft

QUIET PRIVATE zenny retreat with large screened-in deck overlooks NHAL wilderness. Ponder a pine skyline & a plethora of stars! Howling wolves, a floodlight so you can watch it snow at night. Gas grill, firetable. Rustic SAUNA. WIFI, elect FP, kitch, 2 PAIR SNOWSHOES & a trail out the door. LostCanoe Lake, WhiteSand Lake BoatLaunch&Beach, Escanaba & Lumberjack St Trails in 5min. HeartofVilas paved Trl, Fallison Lake St Trl 20min. RusticRd #60 on the way. Semi-secluded yet 8mi to BJ restaurants!

Chalet in Bayfield

4.98 out of 5 average rating, 133 reviews

The Acorn of Little Sand Bay Dog Friendly

Welcome to my new modern-rustic, Aframe cabin in the woods... The Acorn. Beautiful, simple décor, fully equipped kitchen, new appliances, glass stove top, airfryer oven, filtered H2O/ice maker. Enjoy a luxurious bathroom, heated tile floor, walk-in shower, shampoo/conditioner/bodywash provided. King-size bed in the loft area. Smart TV, wifi. Books, games, bluetooth speaker The woodstove heats the cabin perfectly in the colder months. All wood provided. There is also a minisplit heat/ac unit.

Cottage in Herbster

4.98 out of 5 average rating, 248 reviews

Lake Superior's Cranberry River Cottage- The Raven

Enjoy beautiful Lake Superior in the clean cozy modern cottage located in the quaint little town of Herbster where the Cranberry River enters It's just a short couple blocks to the beach and playground. Enjoy the beautiful sunsets, swimming, boating, kayaking, biking, fishing, hunting, and skiing with ATV and snowmobile trails nearby. Explore the Chequamegon Nat'l Forest or venture to Bayfield, home of the Apple Fest, or visit the Apostle Islands Nat'l Lakeshore to see the sea/ice caves.

Guesthouse in Ashland

4.99 out of 5 average rating, 349 reviews

Norrsken Scandinavian Cottage

The guest cottage is painted to resemble a Scandinavian retreat. Complete with separate bedroom, extra fold-out sofa queen bed, kitchenette, wood burning stove, WiFi (the best we can find but not great!!!) and large television (DirecTV), it is a great getaway for a couple or a family. Owners live on property if you need anything. If you are a bit adventurous, we can put up a tent right next to Lake Superior. The entire property is smoke free. For a quiet stay, no snowmobiles or ATVs.

Shipping container in South Range

4.99 out of 5 average rating, 104 reviews

Sölveig Stay: Shipping Container with Nordic SAUNA

Storage containers converted into a Nordic sauna and living space. Set in the woods half a mile from the sandy south shore of LAKE SUPERIOR. Our two-person occupancy and minimal design are curated to re-focus and re-fresh its inhabitants. Located on 80 acres of private land, you will fall in love with the peace and quiet. Whether you’re looking for a romantic couples getaway, spa weekend, or workspace as a digital nomad, Sölveig Stay was designed to spark creativity and relaxation.

Tiny home in Saxon

4.98 out of 5 average rating, 194 reviews

Parker Creek Tiny House

Come stay on our hobby farm with us! We are in a great central location to multiple hiking trails and gorgeous falls. We have had many guests visit the sea caves in Cornucopia, spend the day in Bayfield, or hike the Porcupine Mountains. We also are only a few miles from the ATV trails if you would rather spend the day riding the trails. We have multiple places to mountain bike or kayak. We have more things to do listed in our details section! Feel free to message me with questions.

Home in Ashland

4.87 out of 5 average rating, 152 reviews

Bungalow (House) on Chequamegon Bay.

This newly renovated fully furnished home is located within one block from beautiful Chequamegon Bay, Ashland's Oredock Pier, walking and bike trail, boat ramp, and beach. Grab a pole and head down to fish off the Ashland Oredock pier, or pack up for picnic at the beach, launch your boat, kayak or canoe. Take a walk, bike, or run on the walking trails. It is short walk to a few local restaurants and the downtown area. Access snowmobile trails. No pets are allowed.

Condo in Ashland

4.91 out of 5 average rating, 102 reviews

Main Street apt 2 blocks from Lake Superior!

STELLA South Shore Stay is a new, gorgeous, one bedroom apartment just two blocks from Lake Superior, located on Main Street in Ashland, WI. Enjoy amenities like memory foam mattresses, high-quality bedding, Wi-Fi, all natural skin care, and much more. Walk to Lake Superior in minutes, get a coffee at the Black Cat or a pastry at the bakery, or enjoy the many restaurants and shops on Main Street. You can also enjoy the many local hikes or check out the Apostle Islands.

Cottage in Herbster

4.99 out of 5 average rating, 175 reviews

Applegate Cottage - South Shore of Lake Superior

Applegate cottage is an adorable cottage located just a short walk from the beautiful beach in Herbster, Wisconsin on the Lake Superior Scenic Byway. Whether you like hiking, biking, kayaking, skiing or just relaxing, there’s something nearby for everyone. Bayfield County has orchards, wineries, the Apostle Islands, sea caves, boutique shopping, waterfalls, great restaurants and so much more! Best of all…the sunsets! And, every season brings it’s own beauty!

Yurt in Bayfield

4.95 out of 5 average rating, 325 reviews

Bayfield Rustic Yurt 2 (Terra Cotta)

Nestled in the middle of the Bayfield County Forest, this rustic, minimally maintained yurt has direct access to miles of non-motorized rec trails (mountain bike, cross-country ski and hiking). Enjoy panoramic views of Lake Superior including; Pike's Bay, four of the Apostle Islands (Madeline, Basswood, Stockton and Michigan) and the Upper Peninsula of Michigan. Come prepared to relax, unwind and explore the wonders of the north woods.

Rental unit in Ashland

4.96 out of 5 average rating, 180 reviews

The Garland City Downtown Apartment

1920s, craftsman and art-deco-inspired apartment, furnished with antiques, located in the heart of Ashland’s Main Street Historic District. Ditch the car and walk to local amenities like the grocery store, brewpub, bars, restaurants, shops, library, and movie theater. View Ashland’s downtown murals. The Lake Superior waterfront is steps away...where you can stroll the shoreline path or bicycle the 9-mile town loop.

Vacation rentals for every style

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Popular amenities for Ashland vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Ashland's top sights

Chequamegon Food Co-Op20 locals recommend

Deep Water Grille16 locals recommend

Black Cat Coffeehouse11 locals recommend

Super One Foods7 locals recommend

Ashland Baking Co7 locals recommend

Second Street Bistro7 locals recommend

Other great vacation rentals in Ashland

Cabin in Bayfield

4.97 out of 5 average rating, 99 reviews

Romantic Vineyard Cabin, Sauna, Plunge Pool

Home in Ashland

4.94 out of 5 average rating, 35 reviews

Adventure Homebase

Cabin in Two Harbors

4.97 out of 5 average rating, 186 reviews

Riverwood Hideaway

Cottage in Two Harbors

5 out of 5 average rating, 19 reviews

Secluded Wooded Cottage Near Snowmobile Trails

Guesthouse in Ashland

4.88 out of 5 average rating, 42 reviews

Beach Front Hideaway

Home in Ashland

4.87 out of 5 average rating, 55 reviews

Hidden Vines - Walkable To Murals - Dog-Friendly

Home in Ashland

4.82 out of 5 average rating, 79 reviews

The MacArthur House

Cabin in Wakefield

4.92 out of 5 average rating, 36 reviews

Superior Sunset Cabin

Quick stats about vacation rentals in Ashland

Total rentals
30 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Ashland?
Yes! Work meets play with ease at over 10 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Ashland?
Four-legged friends are welcome in Ashland. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Ashland?
Ashland has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Ashland have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Ashland?
Experience the best of Ashland with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Ashland have wifi?
Absolutely! We offer over 10 house rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

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