Guesthouse vacation rentals in Ashland County

The Pondominium™

Welcome to our Pondominium™ It's a cozy tiny cabin, very private but close to amenities such as restaurants, grocery stores, water falls, Lake Superior, Iron Belle bike/hike trail, Black River Scenic Byway, the Porkies and more! Includes a private driveway, wood fired sauna, shower, microwave, hotplate, k-cup coffee, toaster oven, outdoor gas grill, sleeping loft + sleeper sofa in common area. Located 1 mile off U.S. 2. READ “Other things to note”section about ladder, bathroom, & liability.

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.

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.

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

Siren’s Landing - Funky Island Cabin in the Woods

Welcome to Siren’s Landing on Madeline Island. Your cozy little getaway offers a private guest cabin — the Sun Shack. Enjoy the main cabin, kitchen, living room, and bath house out back, which are all shared spaces. Fall asleep to the frogs singing in the pond. Grill on the back deck. Soak in the sunlight. This place was creatively built by different islanders with much love and I hope you feel it too. It’s also a quick walk to the beach or a short bike ride into town. See you soon!

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.

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.

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.

#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.

The Mill House #1

The Mill House offers five individually styled suites, each designed to give you space to relax while keeping you connected to Bayfield’s downtown energy. With kitchenettes, cozy living areas, and private decks overlooking Bayfield’s First Street and summer gardens, you’ll have everything you need for an easy, memorable stay.

Siskiwit Suite at Great Water Inn

Siskwit is our most affordable option. The space is small but adequate for a two! This room has a large jacuzzi tub and a walk-in shower. A cozy homebase for your northern Wisconsin adventure!

Raspberry Suite at Great Water Inn

Raspberry is our largest single suite. This room has a sitting space, a large jacuzzi tub and a walk-in shower. A cozy homebase for your northern Wisconsin adventure!