Guest house holiday rentals in Ashland County

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Top-rated guest house rentals in Ashland County

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Guest house in Washburn

New place to stay

The Lookout

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

Guest favourite

Private room in La Pointe

4.86 out of 5 average rating, 22 reviews

Siren’s Landing - Funky Island Cabin in the Woods

Welcome to Siren’s Landing on Madeline Island. I have a sweet little private guest house for you. Cozy bed sleeps two. Refresh your spirit in this little nest in the woods. Fall asleep to the frogs singing in the pond. In the shared space (main pic): Grill on the back deck. Soak in the sunlight through antique windows. This place was creatively built by different islanders with much love and I hope you feel it. It’s also a quick walk to the beach or a short bike ride into town. See you soon!

Top guest favourite

Guest house in Ashland

4.99 out of 5 average rating, 363 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.

Guest favourite

Guest house in Ashland

4.89 out of 5 average rating, 45 reviews

Beach Front Hideaway

Attention! G maps suggested route is incorrect. From Hwy 2 - left on 36th, right on Lake Park Rd. Private beach with spectacular views. Kayaks available for a paddle out in the bay or enjoy a sunset from the deck. Also deck heaters and gas grills and a fire pit w/wood. Or Curl up with a good book in front of the indoor fireplace. TV and Wifi too, and a complimentary bottle of wine. A great retreat for 2 couples or a small group of friends. Only 8 minutes from downtown Ashland.

Superhost

Guest house in Washburn

4.86 out of 5 average rating, 14 reviews

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

Top guest favourite

Guest house in Bayfield

5 out of 5 average rating, 57 reviews

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.

Private room in Bayfield

New place to stay

Raspberry Suite at Great Water Inn

Tucked into the heart of Bayfield, Wisconsin, this restored historic lodging is an easy walk to restaurants, shops, hiking, beaches, tour services, and the ferry. Great Water Inn features three suites and one second-floor apartment with a full kitchen and living room. Guests can also rent the entire inn for groups of up to fifteen people. Each room has either a large jacuzzi tub or a private sauna. A cozy homebase for your northern Wisconsin adventure!

Private room in Bayfield

4.28 out of 5 average rating, 25 reviews

York Room

Homemade food, Whitefish Livers and quaint lodgings are what Greunke's Inn is known for in the Bayfield area (and well beyond!) This 137-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.