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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Private cottage situated on a rock bluff located in downtown Baileys Harbor

Bedrooms 2
Property type cottage
Minimum Stay 2 - 7 nights


About the property

2 bedroom, 1 bath private cottage with screened in porch and views of the lake.

Baileys on the Rocks "Rockledge" Cottage is a private cottage located on a small rock bluff in Baileys Harbor, Wisconsin in beautiful Door County. Situated on a secluded wooded lot and directly across the street from Lake Michigan, you’ll find it hard to believe you are in the village of Baileys Harbor and within walking distance of its popular beaches, harbor, restaurants and quaint shops. Located on “the quiet side” of Door County, Baileys Harbor is known for its natural areas, historic lighthouses and outdoor recreational opportunities. It is also the perfect place to relax and the cottages offer the ideal central location from which to explore your interests.

Baileys on the Rocks Cottages consist of two, 2-bedroom cottages, this listing is for the Rockledge Cottage. The historic Rockledge cottage echoes the cottages of yesteryear with a large stone fireplace, comfortable beds and a screened porch with a view of the lake. To view our Arbor Cottage, see our listing VRBO 633251.

More Details

Jessica Dennis
Member since: 2014
Speaks: english, spanish
Response time:
Within a few hours
Response rate:
Calendar last updated:
May 28, 2017

About Jessica Dennis

We are the Dennis Family and we're the proud owners of Baileys on the Rocks Cottages. We're a young family of four that loves to travel and feels at home on the water. We love the energy and excitement of summers in Door County and the peace and quiet of the pristine winters. We're passionate about sharing this little treasure of Wisconsin with our guests.

Jessica Dennis purchased this cottage in 2014

Why Jessica Dennis chose Door County

We purchased this property from a family friend who had owned it for almost a decade. She loved this cottage and cared for it like she would her own home. After spending some time in Baileys Harbor in the winter of 2013 we knew we had found a place we loved. The decision to purchase the cottage was an easy one and we've never looked back. We have many repeat guests and we always welcome new visitors. We love hearing the stories of travelers and what brings them to Door County. We always hope they love it as much as we do.

What makes this cottage unique

We truly have something for everyone. If you're looking for a cozy, older character cottage, Rockledge is a great option for you. The cottage is right across the street from Lake Michigan and centrally located in the Door Peninsula. It is surrounded by the most magnificent trees growing right out of rock and provide peace and quiet that's hard to match anywhere else.


Baileys Harbor Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
  • Housekeeper Optional
House Rules:
  • Max. occupancy: 6
  • non smoking only
  • pets not allowed
  • Minimum Age Limit for Renters ...
  • children welcome
Location Type:
  • Downtown ...
  • Water View ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Coffee Maker
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 4 people
  • 1 Bathroom
  • Bathroom - toilet , combination tub/shower
  • 2 Bedrooms, Sleeps 6
  • Master Bedroom - 1 queen
    Guest Bedroom - 2 twin/ single
    Sofa sleeper - 2 sleep sofa /futon
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Stereo
  • Television
  • Toys
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Long-term Renters Welcome
  • wheelchair inaccessible
  • festivals
  • marina
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • bird watching
  • boating
  • eco tourism
  • paddle boating
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • medical services
Sports & Adventure Activities:
  • cross country skiing
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • kayaking
  • snowmobiling
  • swimming


Wonderful! 4.8/5 -
(34 traveler reviews)

Private cottage situated on a rock bluff located in downtown Baileys Harbor
average rating of 4.7647057 based on 34 reviews

Cottage was clean and had everything we needed for the weekend

  • 5 of 5

Had a very nice and relaxing weekend.

  • Submitted: May 7, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: We're very glad to hear you enjoyed your vacation at the cottage! Thanks again for staying with us.
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Brooklyn WI

Great Thanksgiving Stay

  • 5 of 5

We had a wonderful time for the second year in a row. The cottage is very cozy and in a great location. It's close to town and many parks. We did a lot of hiking on the beaches and took the ferry out to Washington Island. As a break from the norm.....I do a puzzle every year....they offer a good selection of puzzles, games, and books. This was just the break we needed after a very busy year. I would highly recommend staying here!

  • Submitted: Dec 1, 2016
  • Stayed: Nov 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for the great recommendation! We're happy to hear that you enjoyed your stay and some downtime. We would love to host you again in the future.
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Charming and Cozy Cottage

  • 5 of 5

For some time now, my husband and I had hoped to visit Door County. Finally, it came to be, due to a birthday surprise from my very thoughtful husband. I was so excited. After sharing the news with our daughter, she recommended we find a place to stay on VRBO. From it's description on the website, Rockledge Cottage seemed like the perfect place for us and it was! Prior to leaving for our vacation, we were contacted by Jessica. She provided us with all necessary information and great directions. Upon arriving, we found the cottage to be charming, cozy, very clean and well-maintained, just like it was pictured. We arrived later on a Monday afternoon and after getting settled, found a wonderful restaurant in town by the name of Chives for dinner. The service was terrific and the food absolutely delicious. For our first full day and since it was our first visit to Door County, we spent Tuesday exploring the peninsula. We were surprised by how easily we were able to navigate the peninsula. Everything was in close proximity. We visited the many quaint towns, did a little shopping, saw Al Johnson's goats. We visited the lighthouse at Cana Island and saw the amazing views from its tower. We also enjoyed the sunset while sitting on the patio sipping a glass of wine at the Old Post Office. Although we didn't partake, we had a chance to see what a fish boil is like. Thanks to the cottage having a great sports package on the TV, we were able to see the Cubs in action that evening. The furniture was very comfortable and our surroundings so pleasant. In the morning, I especially loved looking out the kitchen window to see the sun rising. As the weather was ideal, we spent our next full day biking in Peninsula State Park. The views, the colors of the leaves and Eagle Bluff Lighthouse were amazing. We did a little more shopping, some wine tasting and, because we loved it so much the first time, we enjoyed another fabulous dinner at Chives. Prior to leaving the next morning, we treated ourselves to a guided tour of the Ridges. So worthwhile and so interesting. Joe and I appreciate so much the opportunity to stay at this charming and cozy cottage. We certainly would stay again and recommend this cottage for your future visit.


Carolyn D.

  • Submitted: Nov 6, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks so much for the awesome review! We're thrilled to hear you enjoyed your stay at the cottage and had a great time exploring Door County. We hope you visit us again in the future - we would love the opportunity to host you.
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  • 4 of 5

Hi Jessica,

Thank you for your clean little home. Overall, we thought the place was very nice. In all honesty, we are not used to paying that much for places, but we understand it was the Sister Bay Festival, which I assume allowed you to charge more. We basically slept there, as we spent most of our time with our friends at their cottage/cabin.

We did not cook there at all, but wanted to heat up a fritter purchased at Seaquist Orchid Farm Market, and the microwave did not work. Disappointing!

So I am sorry that I didn't write to you sooner, so that you can get it fixed before the next family stays. It allowed us to punch in all necessary time, power level, etc. But when hitting the start button, it simply would NOT go.

We have friends who served as wonderful tour guides, so we were able to take in the best "spots" in our short stay. Of course a highlite for us ... as we do this now for the 3rd time, is to ride bikes at Pennisula State Park. It was a gorgeous sunny Sunday, Oct. 16th, to end our visit to Door County.

Thanks again,


  • Submitted: Oct 24, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks so much for letting us know about the issue with the microwave - we will take a look at it as soon as possible to make sure it's in working order for future guests. We're glad to hear that you enjoyed your time in Door County, and we hope you visit again soon.
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Another Great Week in Bailey's On The Rocks Rockledge!

  • 5 of 5

We spent our fourth or fifth visit to Door County the first week of October in the Rockledge Cottage. We always stay there. It has become our home away from home. Our son is 15 now. Our first stay, he was 6. My, how time flies. Anyway, we loved the new mattress in the yellow room so much that we took a photo of the tag to find one at home! We also enjoyed the new coffee maker, couch, TV and DVD/Blu Ray player. The only improvement we would suggest is a new, handheld shower head in the bathroom. The water pressure is pretty low from that shower head and with a handheld one, we could just shower at night and wash or rewet our hair in the morning. Something to think about with several people and one bath. This trip, we did two Segway tours, did a haunted trolley tour, hit the drive-in theater for a double feature, shopped, played putt putt golf and enjoyed a week together with no schedule. We will be back again next year!

  • Submitted: Oct 23, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Wow - that is so exciting that you have been coming back to visit us for 9 years! It is truly an honor hosting you for your Door County vacations. Thank you so much for the helpful feedback about the shower - we appreciate your suggestion.
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Quaint Cottage

  • 4 of 5

We loved the cozy feeling of the cottage. The living room was a lovely place to recharge after a full day of site seeing. Beds were very comfortable. Had a wonderful dinner at Chives!

  • Submitted: Oct 17, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: We're glad to hear you enjoyed your stay in the Rockledge cottage as well as dinner at Chives! Thank you again for staying with us.
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Rates & Availability

Baileys Harbor Cottage Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
Peak Season
Jul 1 2017 - Aug 26 2017
Changeover Day: Saturday
7 night minimum stay
Winter Pricing
Nov 1 2017 - Mar 31 2018
2 night minimum stay
My Standard Rate
2 night minimum stay

Additional information about rental rates

Refundable damage deposit $150
Cleaning and Linens Fee $100 + Tax
Tax Rate 11.0%

During Peak Season (July and August) we require a 7 night minimum stay from Saturday - Saturday.

Please note: unless special arrangements are made in advance, guests need to provide their own bed sheets and towels. Linens and towels are provided by special request and an additional $50 fee will be charged.

Owner's Cancellation Policy

  • 50% refund if canceled at least 14 days before arrival date.
  • 100% refund if canceled at least 30 days before arrival date.

Enter dates for accurate pricing


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