The Pilot House B & B

 
 

The property: Open May 8 – October 31

The Pilot House sits on the original location of the Island View Hotel, an exclusive and popular tourist destination from 1897 until 1916, when it was destroyed by fire. The Pilot House was built in 1994 by a contractor for his family. Subsequent owners converted it to a beautiful Bed & Breakfast. Jack and Marie Armstrong purchased The Pilot House in 2016.

High on a hill overlooking the lake and town, with two decks and large windows, the Pilot House has the best views in all of Bayfield! Relax, sip a drink and take in the sailboats on the bay as the ferry goes back and forth to Madeline Island. Kick back and watch visitors walk the streets in town. The main harbor dock, the ferry, kayak rentals, cruise services, parks, trails, shops and restaurants are just a short walk away.

The Pilot house has 3 suites with private baths—all with lake views. Common areas include a dining room where a light continental breakfast is served every morning from 8–10 am, a living room with a fireplace, octagonal bay area with comfortable seating, and access to the decks overlooking the lake and chairs on the lawn. Guests are free to use the microwave in the kitchen, as well as glasses for water and wine, and ice from the ice-maker. Area information, books, magazines, local papers, cards and games are available in the common area. WiFi is available throughout the property.

Area Information→

Guestbook

⭐️⭐️⭐️⭐️⭐️

We had a wonderful anniversary stay at the Pilot House B&B. The location was perfect, right on the edge of town, but close to shops and restaurants. The lake views were breathtaking from the Crows Nest room and from the main living area, where we found ourselves enjoying quiet nights playing cribbage. Jack was available on the cell phone and quick to respond when needs arose. Much more to see and do!

⭐️⭐️⭐️⭐️⭐️

Reservations were quick and easy to make and we heard back right away. Jack was a hoot...such a story teller. Place is very nice and we had front row seats to the town's fireworks right off the deck. Would like to stay there once when there are not COVID guidelines still needed. I recommend!!

Crows Nest
Crows Nest

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This was an excellent choice for a Bayfield stay! The views were awesome from the Crow’s Nest and deck. The property was very clean. We were walking distance to everything! The Apostle Islands cruise and day trip to Madeline Island on the ferry were worth it! We loved eating at the Copper Trout. Overall an excellent experience.

Crows Nest
Crew's Quarters
Crew's Quarters

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Stayed in the Crew’s Quarters. Very clean, quiet and great location. We enjoyed it. Thanks!

Crew's Quarters
Crows Nest
Crows Nest

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The Pilot House was in the perfect location. Great views and walking distance to the Ferry and shops and restaurants. This was one of the most enjoyable and relaxing vacations I’ve ever had.

Crows Nest
Captain's Quarters
Captain's Quarters

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This is a nice property and Jack is a friendly and helpful host. Very convenient to everything; the ferry, shops, and restaurants. Our room was pleasant and we enjoyed having breakfast on the balcony just outside the dining area.

Captain's Quarters
Crows Nest
Crows Nest

⭐️⭐️⭐️⭐️⭐️

Great location. Our room was at the top of the house and felt very private and secluded. We could see the the lake from every window and lake breezes at night were cooling. Jack was most helpful with great suggestions on places to eat and things to do. Plan to return.

Crows Nest
Crows Nest
Crows Nest

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We loved our stay at the Pilot House. Great location as well accommodations and host!!! We loved it!!! Our room was perfect and the common areas are wonderful. Great deck to sit and have coffee or an afternoon snack. The view was awesome. We will be back, and we will bring our friends and family too!!!

Crows Nest
Captain's Quarters
Captain's Quarters

⭐️⭐️⭐️⭐️⭐️

This is a wonderful property that's nicely furnished, clean and cozy. There are wonderful views of Bayfield, Madeline Island and Lake Superior and everything in town is just a short walk away. Jack and Marie made us feel very welcome and we hope to return here the next time we visit the Bayfield area. Highly recommended!

Captain's Quarters
Crew's Quarters
Crew's Quarters

⭐️⭐️⭐️⭐️⭐️

We enjoyed our 2 night stay in the Pilot House. We would recommend this property to anyone visiting Bayfield.

Crew's Quarters
Captain's Quarters
Captain's Quarters

⭐️⭐️⭐️⭐️⭐️

Great location....nice place

Captain's Quarters
Admiral's Quarters
Admiral's Quarters

⭐️⭐️⭐️⭐️⭐️

Enjoyed our stay and the Pilot House is very nice, we would stay there again.

Admiral's Quarters
Admiral's Quarters
Admiral's Quarters

⭐️⭐️⭐️⭐️⭐️

Jack, our host, was friendly, knowledgeable, and an amateur comedian. We had a very relaxing stay and experience.

Admiral's Quarters
Captain's Quarters
Captain's Quarters

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We had a very nice stay and Jack was a great host! Stayed in the Captain's Quarters and loved the view outside. Took in the last day of Apple Fest in Bayfield and had a ball. Jack offered Bungy jumping off the roof but it was too wet to try.... lol. Seriously, the Pilot House is a great place to stay we highly recommend it!

Captain's Quarters
Captain's Quarters
Captain's Quarters

⭐️⭐️⭐️⭐️⭐️

We had a very nice stay and Jack was a great host! Stayed in the Captain's Quarters and loved the view outside.

Captain's Quarters
Crows Nest
Crows Nest

⭐️⭐️⭐️⭐️⭐️

We loved our stay in the Crows Nest, the view was stunning and Jack was very welcoming! We can’t wait to go back!

Crows Nest
Captain's Quarters
Captain's Quarters

⭐️⭐️⭐️⭐️⭐️

The Pilot House is a beautiful bed and breakfast filled with windows that look out onto Bayfield and Lake Superior. Our sparkling clean room had a very comfortable king size bed, and the shower had great water pressure. We would absolutely stay there again!

Captain's Quarters
Crows Nest
Crows Nest

⭐️⭐️⭐️⭐️⭐️

Charming! Jack makes you feel right at home.

Crows Nest
Crew's Quarters
Crew's Quarters

⭐️⭐️⭐️⭐️⭐️

Great place. Jack is informative and fun. He makes the stay very enjoyable.

Crew's Quarters
 

Video of The Pilot House

Two Night Minimum

Three Night Minimum AppleFest Weekend

No Pets (Owners dogs Chester & Oscar may be on site, but only when accompanied by owners)

Primary Renter Minimum Age 21

 

admiral’s quarters

On Main Level, Lake Views, Skylights

Sleeps up to 4, Children Welcome

1 King Bed, Nightstand, Alarm Clock

1 Queen Sofa Sleeper, 6” Mattress

Private Bathroom, Jetted Tub, Shower

Linens/Towels/Soap/Shampoo/Conditioner

Walk-in Closet, Dresser, Table & Chairs

32" Flat Screen Roku TV, WiFi

Hairdryer

Mini-Fridge, In-Room Coffee

Microwave & Ice in Kitchen

Private Door to Deck

Central Air; In-Floor Heat; Thermostat

B&B Coded Entry, Chainlock on Suite

Smoke/CM Alarms, Fire Extinguisher

Exterior Lights, Night Lights

Steep Driveway

Parking for 1 Car/Suite, More On Street

 

Crew’s Quarters

Newly Remodeled in 2019 (last 4 pictures)

On Lower Level, Limited Lake & Town Views

Sleeps 2, No Children

1 King Bed, Nightstand, Alarm Clock

Private Bathroom, Tiled Shower

Linens/Towels/Soap/Shampoo/Conditioner

Dresser, Closet, Table & Chairs

32" Flat Screen Roku TV, WiFi

Hairdryer

Mini-Fridge, In-Room Coffee

Microwave & Ice in Kitchen

Central Air; In-Floor Heat; Thermostat

B&B Coded Entry, Chainlock on Suite

Smoke/CM Alarms, Fire Extinguisher

Exterior Lights, Night Lights

Steep Driveway

Parking for 1 Car/Suite, More On Street

 

Crow’s Nest

On Top Level, Lake/Town Views

Sleeps 2, No Children

1 King Bed, Nightstand, Alarm Clock

Private Bathroom, Jacuzzi Tub, Shower

Linens/Towels/Soap/Shampoo/Conditioner

Dresser, Closet, Table & Chairs

32" Flat Screen Roku TV, WiFi

Hairdryer

Mini-Fridge, In-Room Coffee

Microwave & Ice in Kitchen

Central Air; Heat; Thermostat

B&B Coded Entry, Chainlock on Suite

Smoke/CM Alarms, Fire Extinguisher

Exterior Lights, Night Lights

Steep Driveway

Parking for 1 Car/Suite, More On Street

15 Windows, Spectacular Views