
Family-friendly vacation rentals in Ashland
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Ashland

Total vacation rentals
Explore 20 vacation rentals in Ashland

Nightly prices starting at
Ashland vacation rentals start at G$16,734 GYD per night before taxes and fees

Verified guest reviews
Over 1,480 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Ashland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Ashland rentals

4.9 Average rating
Ashland stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated family-friendly rentals in Ashland
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Bayfield Rustic Yurt 1 (Evergreen)
Set in the middle of the Bayfield County Forest and explore thousands of acres of public land and enjoy miles of non-motorized recreational trails. The yurt has direct access to CAMBA mountain bike trails and Mt. Ashwabay ski trails. Take in the panoramic views of Lake Superior and the Onion River valley. This is a hike in only (3/4 mile up hill), rustic, minimally maintained yurt with outhouse and no running water. Once here, prepare to relax, unwind and explore the wonders of the north woods.

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.

The MacArthur House
Four generations of our family have resided at The MacArthur House. Formally a farm house it is a quaint & charming home with many of its original features. The kitchen has a chalkboard that came from one of the local schools. The house is located in a quiet residential neighborhood in close proximity to the local schools,colleges & hospital. We are licensed. We love animals, but we do not invite pets to stay on our property. We also do not allow smoking, or tobacco anywhere on our property.

Cedar Ridge | Hand-Crafted Cabin with Lake Views
This newly built cabin will take your breath away. You’ll find the perfect blend of Northwoods rustic charm and creature comforts in this 3 bdrm cabin nestled in the woods overlooking Lake Superior’s Bark Bay. You’ll fall in love with all the care & attention its owners have put into every detail. From the stunning cedar beams that provide the backdrop to the incredible lake views to the hand-crafted interior woodwork and the beautiful kitchen, you will see how unique and special this cabin is.

Cedar Hill Retreat, King Bed, 108 Acres of Privacy
Winding up the driveway you are greeted by a home located on 108 acres of privacy, yet only 8 miles from town! This place is a clean (enhanced cleaning routine), fresh, and relaxing with breathtaking views! With enough space for a whole group or private couple getaway, this home offers the perfect opportunity to make memories lasting a lifetime. Gather around the wood stove after a long winter day full of activities available close by, or relax on the back deck watching the sun set in summer!

Superior Sanctuary: Refined Rustic in the Woods
Escape to the tranquil shores of Lake Superior in our charming retreat! Nestled within the serene Brickyard Creek Community, this modern haven offers a perfect blend of rustic elegance and contemporary comforts. Immerse yourself in nature's beauty, unwind on the spacious screened porch, and cozy up by the fireplace. Your peaceful escape awaits. • Screened Porch with Swing Chairs • Access to Beach and Hiking Trails • Smart TV & Streaming • Modern Kitchen • Boat Slip Rental Available

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.

Off grid glamping at a Rockhound Hideaway
A perfect glamping retreat awaits you at Rockhound Hideaway's Agate Grove Bell Tent. Situated on a private two acre lot with two other rentals and my private residence in the Ottawa National Forest, steps from the Black River, North Country Trail and a one mile walk to the Lake Superior Shore, this is an ideal getaway for those seeking the adventure of camping with the comforts of home. Fall asleep to the sound nature and wake up to deer passing by as you enjoy your morning coffee.

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.

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.

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.

Come love the south shore of Lake Superior
The Cornucopia Sweet Retreat is a unique open concept living space above Corny Coffee in Cornucopia, Wisconsin. We are just steps from Lake Superior and 4.6 miles from the Meyers beach ice caves and hiking trail to over look the ice caves. In summer the caves can be seen by kayak or from the hiking trail. We are also located 20 minutes from Bayfield, Wisconsin and the ferry to Madeline Island. The Cornucopia Sweet Retreat is a no smoking / no pet space.
Popular amenities for Ashland family-friendly rentals
Family-friendly home rentals with a hot tub

Hot Tub • Fireplace • Dog Friendly•Big Powderhorn

Handcrafted Log Cabin | Hot Tub | Sauna | GameRoom

Hot Tub | Sauna | King Bed | AC | Pets |Micro Farm

Luxury Cabin on Big McKenzie - Hot Tub & Serenity

Hot Tub • Fireplace • Dog Friendly •Big Powderhorn

Cute & Cozy 1B/1B Condo w/ Jetted Tub!

* New, Luxury* The Powerhouse Loft

Indianhead duplex chalet with a hot tub 2376
Family- and pet-friendly home rentals

The Red Onion House near Bayfield

Guest House

Marengo River Bluff Cabin

The Copper Squirrel of Little Sand Bay DogsWelcome

Stunning Bark Point Home on Superior's South Shore

Sunrise Lake View 2 • Walk to Downtown Bayfield

Lake Delta Deer Trail Delight

Sky Fire | Lake Superior Waterfront Retreat
Family-friendly home rentals with a pool

One Minute Walk to Lake Superior. Brookside #3

Brookside Hideaway #6

Hidden Gem, 3 Bed Cozy Condo - Dogs Welcomed

Brookside Hide-A-Way #2, Port Superior, Bayfield

Superior Lakefront 1BR|Pool • Hot Tub • Sauna • EV

Breathtaking Lake Views 1BR w/King Suite & Pools

Wooded Lake Superior Escape-views, deck, fireplace

Lake Superior Condo~Resort Amenties
When is the best time to visit Ashland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,166 GYD | G$36,605 GYD | G$31,166 GYD | G$35,559 GYD | G$40,788 GYD | G$40,788 GYD | G$38,697 GYD | G$39,952 GYD | G$41,416 GYD | G$41,207 GYD | G$30,539 GYD | G$29,284 GYD |
| Avg. temp | -12°C | -9°C | -3°C | 4°C | 11°C | 16°C | 19°C | 19°C | 14°C | 7°C | -1°C | -8°C |
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