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

The Crooked Cottage - A 100 Year Old True Cottage Style Home

Bedrooms 6
Space 1,640 sq. ft.
Property type cottage
Minimum Stay 3 nights


About the property

A 6 Bedroom 2 Bathroom Wonderment Of A Beach House Right On Lake Michigan

Our Cottage is currently for sale. If you are interested in purchasing the Crooked Cottage, please contact me. However, until further notice, we will not be taking any more rentals. Thank you.

The Crooked Cottage is a cozy hundred year old hideaway with everything you need for your enjoyable beach vacation. An original Sheridan Beach home from 1915 it is as authentic as it gets. There is ample parking, a direct path to the beach, An out door shower and a large deck for hanging out on. The kitchen comes fully functioning and there is lots of room on the ground floor for watching cable TV, dining, playing games, or just relaxing with a book. The back porch has a second refrigerator to store extra drinks or snacks for the beach, and we have a wide selection of beach chairs that are easy to bring back and forth. There is a bathroom both upstairs and down stairs, each with its own shower. The house has an air conditioning system or a heating system, as well as ceiling fans and portable floor fans for all the bedrooms. The beach itself is on the lovely Lake Michigan and is a perfect place for playing in the water, going on walks or just hanging out in the refreshing beach atmosphere. The house is perfectly suited to accommodate large groups or families with children and locations nearby can provide appropriate entertainment and dining in either case for days when you have had too much beach. All rooms are fully decorated and come with spare bedding and bath towels. In the case of extra people overnight, there are two inflatable mattresses in the closet of the family bedroom and both down stairs couches are comfy for sleeping. Our cottage only books Family vacations, please.

John Condon
Member since: 2014
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
June 27, 2017

About John Condon

I grew up right here in Michigan City, it's a great place to live, a great place to stay. Renting is my second successful business, the first being an advertising service based in Chicago. Although I currently live in Illinois, I take every opportunity I can to visit the old home town. My hobbies include boating and painting, in fact much of the artwork you will see in the Crooked Cottage is original work.

John Condon purchased this cottage in 2010

Why John Condon chose Michigan City

This House is one of the Best on the market. Lake Shore Drive is a very scenic in the first place, and the Crooked Cottage itself is within easy driving distance of the many attractions that Michigan City offers. The House is about a hundred years old, so it is never lacking in character. Our direct beach access lets out onto a magnificent shoreline that never gets too crowded and always has the best sunset views. Plus two doors down there's a castle!

What makes this cottage unique

The atmosphere is relaxed, the house is as close as it gets to the beach with a charming walk through a tree lined path to the dunes and beach. The house gets shade, sun and most importantly privacy where many others don't. The deck is extra sized and includes plenty of comfortable seating and napping space. The walk out to the light house is just about a mile there and back and makes for very pleasant exercise. this particular stretch of beach is just the right balance between empty and crowded. There is always more than enough room to stretch out, but if you are the social type, new friends are just down the beach. the sand is smooth and soft, perfect for sand castles.


Michigan City Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 1640 sq. ft.
House Rules:
  • Check-in: 4:00 PM / Check-out: 10:00 AM
  • Max. occupancy: 13
  • Minimum Age Limit for Renters
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Beachfront
  • Lakefront
  • Waterfront
  • Away From It All
  • Family
  • Air Conditioning
  • Fireplace
  • Heating
  • Internet
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining
  • Dining Room
  • seating for 8 people
  • 2 Bathrooms
  • upstairs bathroom - toilet , combination tub/shower
    downstairs bathroom - toilet , shower
    The Nature Experience - outdoor shower , hot water and a shower head when hose in on
  • 6 Bedrooms, Sleeps 13
  • master bed room - 1 king
    family bed room - 1 queen , 1 bunk bed
    front bed room - 1 king
    corner bed room - 1 queen
    single bed room - 1 twin/ single
    bunk bed room - 1 bunk bed
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Television
  • Toys
  • Video Library
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • wheelchair inaccessible
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
  • water parks
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • gambling casinos
  • horseback riding
  • miniature golf
  • outlet shopping
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • sledding
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • sailing
  • snorkeling
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing


4.6/5 -
(5 traveler reviews)

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The Crooked Cottage - A 100 Year Old True Cottage Style Home
average rating of 4.6 based on 5 reviews
Illinois, USA

It's a great cottage with excellent owners

  • 4 of 5

Location, location, location. Property owners are super nice and accommodating. It's a 100 year old prototypical lake cottage, if you don't know what that means, this probably isn't for you. If you want a McMansion to impress your guests, this isn't for you. This is a great place that exudes charm and quirky touches that draw you in and makes it feel like a home. May actually contribute to enjoying time with the extended family. If you are laid back, artsy, like some character, and enjoy the beach, this is for you. Social climbers and Mad Men wannabes, I think not so much. Thanks for a great stay, we had a blast.

  • Submitted: Aug 6, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
Owner's Response: Perfect description of our cottage, so glad your group had a blast!
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A great place for a multi-family vacation.

  • 5 of 5

We had a wonderful stay at The Crooked Cottage and the owners were easy to work with. The bedroom arrangements worked great for our family of 8 adults and 5 kids (1-13). The house was clean and well maintained. There was plenty of cookware and dinnerware and a beautiful large grill. Also lots of games and beach accessories. It was great to walk down the path to the beach without crossing a road. We spent mornings and afternoons at the beach, but we could have done other things in the area. There's a small zoo close by and other attractions, but the weather was perfect everyday so we were happy with just digging in the sand and jumping in the waves at the beach. We spent the evenings playing games on the deck and walking back to the beach for the sunset. Shopping and restaurants were a short ride away. We all enjoyed our family gathering at Crooked Cottage.

  • Submitted: Aug 9, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
Owner's Response: The Crooked Cottage is very thankful to hear that your family enjoyed their stay. We appreciate your review.
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0 0

Crooked Cabin for family reunion

  • 5 of 5

We stayed in the Crooked Cabin for a long weekend in July for a family reunion and had several generations and people of all ages. The house really exceeded our expectations. It was very comfortable for a large group, even when the weather did not cooperate. The house is nicely decorated and well-stocked for a beach vacation. It had everything that we needed, even two full sized refrigerators and plenty of parking. The HVAC is new and worked well in hot weather. We would definitely stay again.

  • Submitted: Aug 8, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
Owner's Response: The Crooked Cottage is very thankful to hear that your family enjoyed their stay. We appreciate your review.
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1 0

Great vacation home for our group of friends!

  • 4 of 5

This vacation was the second annual one for our group of friends. Our home last year was more spacious and more modern than this home so some members of our party were skeptical. The Crooked House won them over! The location was great and the beach was beautiful. The walk over the dune to the beach was harder for some than others (and the sand was HOT) but it was easy enough that we travelled back and forth many times each day. We were glad that we didn't need to cross a busy street with kids and gear in tow. The home was clean and comfortable. And, as advertised, charming. I loved the wicker front porch. The deck had enough seating for all 13 in our party to dine outdoors plus there was plenty of seating indoors. A variety of beach toys, beach chairs and games for indoors were provided. We wished for one more bathroom but made due. The owners were flexible with arrival and departure times and quickly refunded our security deposit. We had absolutely no complaints and would recommend this home to friends and family.

  • Submitted: Aug 2, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
Owner's Response: The Crooked Cottage is very thankful to hear that your family enjoyed their stay. We appreciate your review.
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2 0

A wonderful time on Lake Michigan

  • 5 of 5

This is our second time at the Crooked Cottage, and we would highly recommend and will definitely consider coming back again. The owners were very accommodating. The space is cozy and big enough for a large family gathering. The beach was amazing - crystal clear water, soft sand, even a sand bar out a bit into the beach to play on. Lots of nooks for quiet reading and big gathering spaces for being together.

  • Submitted: Jun 27, 2016
  • Stayed: June 2016
  • Source: VRBO, from HomeAway
Owner's Response: The Crooked Cottage is very thankful to hear that your family enjoyed their stay. We appreciate your review.
Did you find this review helpful?
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Nearest Airport
90 Miles
South Bend Airport
Nearest Barpub
0.5 Miles
Shoreline Brewery
Nearest Golf
3 Miles
Michigan City Municipal
Nearest Train
0.5 Miles
Nearest Motorway
3 Miles
Highway 94
Nearest Restaurant
0.5 Miles
Swing Bellies
Nearest Beach
100 Metres
Sheridan Beach
Car: necessary


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $1,000
Cleaning fee $200
Tax Rate 12.0%

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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