Guesthouse vacation rentals in Ashland County

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Top-rated guesthouse rentals in Ashland County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming red cottage is nestled among tall trees, showcasing a welcoming front with two white Adirondack chairs placed on a natural surface. Decorative flower arrangements hang near the entrance, surrounded by lush greenery and plants.

Guesthouse in Ashland

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.

ValueFamilySolo travel

4.99 out of 5 average rating, 418 reviews

A cozy cottage is nestled among snow-covered trees, showcasing a unique exterior with stone accents and a sloped roof. Snow blankets the surrounding ground, creating a serene winter scene. A lantern near the entrance provides a quiet illumination, enhancing the cabin's welcoming appearance.

Guesthouse in Washburn

Glamping Cabin at Whitecap Kayak Learning Center

Your own personal cottage in the forest at Whitecap Kayak Learning Center, a base camp for local kayak guiding and instruction. During the kayak season, our guides stay here. In the off season, we can share it with new friends. You will find a cozy and warm spot in the forest. Expect a small walk to the bathrooms, showers, and running water. You can snowshoe around the property, ski at many local trails or Mt Ashwabay, and enjoy life in the beautiful Washburn and Bayfield area

LocationWalkabilityCondition

4.8 out of 5 average rating, 15 reviews

Guest favorite

Guesthouse in Bayfield

Modern Private Suite w/Free Breakfast&Free Parking

FREE BREAKFAST AT MANYPENNY BISTRO! Enjoy a peaceful stay in our beautiful guest house with a view of Lake Superior and your own private entrance; offering comfort, privacy, and a relaxing atmosphere. Suite is steps away from our home and a short 5 minute walk to Bayfield. Our charming suite offers a cozy queen-size bed, an additional sofa bed and has a modern kitchenette with a coffee bar. Additionally, enjoy a full, luxurious bathroom with a shower, and a lighted faucet.

LocationFamilyIndoor spaces

4.88 out of 5 average rating, 16 reviews

Top guest favorite

A cozy guest house interior is presented, featuring a spacious bed covered in a colorful patterned quilt. A kitchenette with a stove and fridge is visible, complemented by a dining table and seating area. Large windows allow natural light to illuminate the space.

Guesthouse in Washburn

The Lookout Suite

This newly renovated guest house studio w/ kitchenette has a private 2nd fl entrance and outdoor wraparound deck to enjoy the tree tops. House is located on same property as owner. This is a separate outbuilding that you will have all to yourself. Complete kitchenette, stove, fridge, and grill, hammock, outdoor seating, and private spaces to enjoy. Kick back in this calm and cozy space. Dogs are welcome :) There is a friendly Chesapeake Bay Retreiver on the property.

LocationBeachComfort

4.89 out of 5 average rating, 53 reviews

Top guest favorite

A private deck is visible, furnished with a dining table and chairs under a red umbrella. Lush green trees surround the cottage, enhancing the natural setting. A stone pathway leads from the yard to the deck, emphasizing the serene outdoor space.

Guesthouse in Bayfield

Seclusion in the Pines - A Hidden Gem in Bayfield

Rittenhouse Pines Cottage is a one-of-kind rental! It's a secluded getaway overlooking a ravine surrounded by towering pines. And it's close enough (seven blocks) to all downtown Bayfield has to offer! Since it's the guest cottage adjacent to our home (although it's about 1/2 block away), our three friendly dogs are used to having the run of the place. We'll keep them close to home during your stay but if you aren't a fan of dogs, this may not be the cottage for you.

FamilyLocationBathroom

5.0 out of 5 average rating, 86 reviews

Top guest favorite

The image depicts a sandy shoreline bordered by smooth, dark stones along a calm bay. Lush greenery lines the water’s edge, with scattered trees in the background. The overcast sky creates a serene atmosphere, inviting peaceful walks along the beach.

Guesthouse in Ashland

Beach Front Hideaway

Private beach with spectacular views. Kayaks available for a paddle out in the bay or enjoy a sunset from the deck. Also 2 bikes, fishingpoles, deck heaters, gas grills and a fire pit w/wood. Or Curl up with a good book in front of the indoor fireplace. 1 bed, 1 high end sofa sleeper. TV and Wifi, and a complimentary bottle of wine. A great retreat for 2 couples or a small group of friends. Only 8 minutes from downtown Ashland.

LocationValueCheck-in

4.92 out of 5 average rating, 86 reviews

Private room in Bayfield

#5 Queen Bed with shared bath, a/c, WIFI.

Homemade food, Whitefish Livers and quaint lodgings are what Greunke's Inn is known for in the Bayfield area (and well beyond!) This 162-year-old Historic Inn is located in the heart of downtown Bayfield. One block from Lake Superior, the Madeline Island Ferry, Apostle Islands Cruise Service and the several great shops in the downtown area.

LocationValueAir conditioning

4.67 out of 5 average rating, 140 reviews