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Holiday Rentals and Homes in Chesterton, IN

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    1 / 16
    5 of 5 stars (1) Excellent
    Chesterton
    5 Bedrooms, 3 Bathrooms, Sleeps 20 | Quick View
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    The following rentals are within 25 kilometers of Chesterton, Indiana.

    1 / 35
    5 of 5 stars (8) Excellent
    Michigan City
    6 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    Michigan City
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    1 / 28
    5 of 5 stars (1) Excellent
    Michigan City
    4 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Terrace
    • Parking
    • Wi-Fi
    • Balcony
    • Outdoor Dining Area
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our Sheridan Beach vacation home is newly renovated, completed in mid August 2015. We put in a brand new kitchen with hickory cabinets, quartz counter tops, and a butcher block island. The kitchen is open to the living and dining area, which provides a nice open area for your group to gather! There... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 2 weeks ago
    very clean, lots of room, close to the beach, restaurants, Matey's was a blast! We really enjoyed our stay this week and we traveled to Chicago 3 times, not too far. A/C...
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    1 / 44
    5 of 5 stars (10) Excellent
    Michigan City
    7 Bedrooms, 5 Bathrooms, Sleeps 24 | Quick View
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    • Children's Pool
    • Satellite TV
    • Patio
    • DVD Player
    • Washer
    • Housekeeping...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in the Indiana Dunes' acclaimed Beachwalk Resort community on one of Lake Michigan's most beautiful stretches of beach, Sun King is an incredible home fit for a crowd with the charm of a classic beach bungalow with wrap around porch. This one-of-a-kind home comes complete with the usual... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 19 May 2016
    Our family rented this beautiful cottage for my wedding shower in April - it was perfect! We had 10 kids under the age of 7, and they loved playing in the huge basement. And...
    5 of 5 stars Reviewed 8 February 2016
    We had a great time!! The house was very accommodating, there were 18 of us all together, we had plenty of room. We enjoyed the fireplace, and had a blast playing ping pong...
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    1 / 14
    4.5 of 5 stars (3) Very good
    Michigan City
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Washer
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Warm cozy constructed lake house "Southern Belle" - located in the beautiful Beachwalk Resort community in Michigan City, Indiana. Five bedrooms and 4 1/2 bathrooms. Home can accommodate up to 14 adults with beds and dining. This home has two master bedrooms. The larger master is located on the... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 6 days ago
    We just checked out of the Southern Belle. Grandparents, siblings, spouses, nieces and nephew all enjoyed the home, location, activities, and proximity to so many adventure...
    5 of 5 stars Reviewed 15 June 2015
    I have stayed at several cottages around the Michigan City area and this is by far the nicest. Extremely well kept; with more than enough room for larger groups. Great location...
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    1 / 9
    4.5 of 5 stars (3) Very good
    Michigan City
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • DVD Player
    • Balcony
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    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Warm cozy lake house in the beautiful Beachwalk Resort community in Michigan City, Indiana. Two bedrooms and 1 1/2 bathrooms. All finishings and decor are of the highest quality with stainless steel appliances, granite countertops, fireplace and hardwood floors throughout. All small appliances,... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 1 June 2015
    Would definitely return every year! More than I expected!!! went for a weekend getaway with the wife and kids. The booking process was easy and the owner very friendly. Wanted us...
    5 of 5 stars Reviewed 30 May 2015
    Our family - 2 adults and 3 children- stayed a week at this house in August. This was my first visit to Michigan City and the Beachwalk community and we all had an amazing week...
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    1 / 24
    5 of 5 stars (1) Excellent
    Michigan City
    6 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    • Ocean Views
    • Wi-Fi
    • Patio
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This vacation home is on a sand dune directly on Lake Shore Dr, across the street from the beach access path to Lake Michigan. Wake up to views of Lake Michigan. Step out onto the 2nd floor deck off the master bedroom and have a cup of coffee as you gear up for a great day at the beach! There is a... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 30 August 2015
    Our big extended family rented this nicely furnished home for a week in July for our summer vacation. Plenty of room for our huge group to sleep. The layout of the kitchen and...
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    1 / 16
    4.5 of 5 stars (9) Very good
    Michigan City
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This 2 bedroom apartment has a large kitchen, living room, 2 bedrooms and a bathroom. It has a queen size bed in one room and 2 twin beds in the other room. We are located directly across the street from the Lighthouse Outlet Mall. This mall has 120 stores, great shopping, people come from all... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 3 weeks ago
    We rented three apartments at once the two bedroom, the yellow one bedroom, and the red apartment for the family gathering. We arrived to enjoy the Washington Zoo with the...
    5 of 5 stars Reviewed 16 June 2016
    My family and I enjoyed staying in this rental it was cozy and like being at home with all the conveniences and very secure. Close to all attractions. Best of all Darlene (the...
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    1 / 16
    4.5 of 5 stars (10) Very good
    Michigan City
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Charming apartment upstairs. Has a full kitchen, dishwasher, breakfast bar, queen size bed/couch,loveseat and complete turn-key for your stay. We are located directly across the street from the Lighthouse Outlet Mall. This mall has 120 stores, great shopping, people come from all over the... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 1 week ago
    My husband and I traveled with his sister and her husband. We had such a great time. This location is close to anything you would like to do. The Washington Park Beach was our...
    5 of 5 stars Reviewed 2 weeks ago
    This apartment was great. Darlene, the owner is great and has a wonderful place. It's close to everything you could want. The beach at Washington State Park was our favorite. If...
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    1 / 13
    5 of 5 stars (8) Excellent
    Michigan City
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Internet Access
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Charming upstairs apartment. Has a full kitchen, dishwasher, breakfast bar, queen size bed etc. We are located directly across the street from the Lighthouse Outlet Mall. This mall has 120 stores, great shopping, people come from all over the country to shop. If you stay with us you will have an... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 4 weeks ago
    My 7 year old daughter and I stayed for a week while my oldest was at camp in Southwest Michigan. This was the PERFECT place for an extended stay. Although at first glance the...
    5 of 5 stars Reviewed 21 June 2016
    The reviews and descriptions don't lie, this is a great place to stay. Located across the street from the outlet mall and walking distance to the arts district, it has a lot to...
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    1 / 16
    5 of 5 stars (16) Excellent
    Michigan City
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Charming apartment open concept. Has a full kitchen, dishwasher, breakfast bar, queen size bed/couch and complete turn-key for your stay. Wonderful lWe are located directly across the street from the Lighthouse Outlet Mall. This mall has 120 stores, great shopping, people come from all over the... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 1 week ago
    My mother and I stayed in the red apartment and it is so cute! Everything you could possibly think of needing has been provided by the owner in all of the drawers. A quick or...
    5 of 5 stars Reviewed 2 weeks ago
    A year has passed since my last stay here... And the place only got better! It was five stars before and now it is five +. The front porch and yard are gorgeous and the perfect...
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    1 / 11
    5 of 5 stars (1) Excellent
    Michigan City
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Children's Pool
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    OPENING IN MAY 2016! New warm cozy lake house in the beautiful Beachwalk Resort community in Michigan City, Indiana. Two bedrooms and 2 1/2 bathrooms with basement. Kitchen furhishing are hig quality with stainless steel appliances, granite countertops, fireplace and hardwood floors in main area... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 19 June 2016
    The Blueberry Cottage was a wonderful place the stay. The neighborhood is very quaint. Our contact Matt was very helpful from start to finish. The interior gives one the feeling...
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    1 / 14
    Michigan City
    4 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    You can rent a year-round home in Grand Beach, MI. for a relaxing 1-2 week vacation by the shores of Lake Michigan. Great shopping, restaurants, antiquing, casinos, wineries or simple, quiet, walks on the shore are a short drive away. Just pack your bags, go, and lock the door when you leave.... View all property information
    Location Information
    Michigan City, Indiana 49117
    Long Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful Playa Casa Long Beach is a sun light filled happy home. One hour drive from Chicago's loop, one of the best white sandy beaches on the great Michigan Shore. One big open space, a fully equipped gourmet kitchen, dining room, great room and den area is very social friendly. The... View all property information
    Location Information
    Long Beach, Indiana 46360
    Michigan City
    7 Bedrooms, 4 Bathrooms, Sleeps 17 | Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy beautiful white sand beach, great outlet shopping or the casino while staying in our Arts and Crafts home perched on a dune with a 180 degree view of the lake. Hang out at the beach just across the street and down the path in summer and in winter, listen to the noises of the lake and enjoy... View all property information
    Location Information
    Michigan City, Indiana 46360
    Valparaiso
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Private Garden
    • Secure Parking
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This guest house is located on private property inside Lake O the Woods Club. The oldest continually operating Nudist Club in the United States. You will have access to 203 private acres with hiking paths, a 27 acre lake, heated pool, 12 person hot tub and sauna. Very private, this is the perfect... View all property information
    Location Information
    Valparaiso, Indiana 46383
    1 / 14
    5 of 5 stars (1) Excellent
    Michigan City
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Central Heating
    • Grill
    • DVD Player
    • Patio
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Pineapple Retreat is located in Michigan City's acclaimed Beachwalk Resort Community. Beachwalk hosts a variety of things to do. We have our own private Lake Kai, beach volleyball, heated swimming pool, playground for the kids, tennis courts, basketball court, putting green, and park. Located... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 22 June 2016
    My family and I had another great vacation at the Pineapple Retreat! We couldn't believe it had already been 5 years since we had been there before and we don't know why we waited...
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    Michigan City
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Patio
    • Balcony
    • Grill
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    • Internet Access
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Mythology and the perfect beach holiday meet in this charming 2-story guest house that feels as though it were straight out of a fairy tale. The Troll's Den sleeps 6 people with 3 bedrooms and 2 baths, full kitchen and laundry facilities. This house is perfect for families or small gatherings, with... View all property information
    Location Information
    Michigan City, Indiana 46360
    Michigan City
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Satellite TV
    • Washer
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    • Internet Access
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This almost-new, four bedroom home has a vaulted pinewood ceiling and fabulous fieldstone fireplace in the great room which adjoins the dining area and knotty-pine kitchen. Large screened-in porch is nestled between the great room and four-car attached garage. The gang will spend hours on the... View all property information
    Location Information
    Michigan City, Indiana 46360
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    1 / 9
    Michigan City
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Balcony
    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Perfect for your family vacation. Luxury lakehouse available in the beautiful Beachwalk Resort community in Michigan City, Indiana. Two bedrooms and 1 1/2 bathrooms. Home can accomodate up to 6 adults with beds and dining. This home has bedrooms, one with a queen bed and the other with two twin... View all property information
    Location Information
    Michigan City, Indiana 46360
    1 / 18
    Michigan City
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Private Outdoor...
    • Patio
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    Perfect for your family vacation. Luxury lakehouse available in the beautiful Beachwalk Resort community in Michigan City, Indiana. Five bedrooms and 4 1/2 bathrooms. Home can accomodate up to 14 adults with beds and dining. This home has two master bedrooms. The larger master is located on the... View all property information
    Location Information
    Michigan City, Indiana 46360
    Michigan City
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Convenience and accessibility are among many reasons to consider vacationing at "Il Giardino." The home is situated approximately one mile from the lake, (10 minute drive)set in a tranquil landscaped backdrop made up of firs, flowering shrubs, and a waterfall feature. Courtesy parking passes are... View all property information
    Location Information
    Michigan City, Indiana 46360
    1 / 42
    5 of 5 stars (3) Excellent
    Michigan City
    7 Bedrooms, 8 Bathrooms, Sleeps 24 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The Queen Bee, along with its included coach house, Buzz Inn, are not to be missed. This massive property is perhaps Beachwalk’s largest and, under new ownership for 2016, has been transformed into its nicest. Seven bedrooms and eight bathrooms spread across six separate floors of living, with... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 16 June 2016
    Queen Bee and Buzz Inn were exceptional in capacity, location, decor, and hospitality. There was nothing lacking!! We had an extended family of 21 which included 6 children...
    5 of 5 stars Reviewed 29 April 2016
    We absolutely loved the Queen Bee! It is spacious, well appointed, and perfect for large families or groups. The guest house is great for the matriarch and patriarch or a small...
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    1 / 8
    4.5 of 5 stars (9) Very good
    Michigan City
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
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    • ?
    • ?
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    • x
    About this property
    Can't decide between the hustle and bustle of a casino getaway or the relaxation of a beach weekend getaway, this home is a great option. There is a large backyard for playing with the kids and a small sandbox for the little ones to keep busy close to home. Year round residents on either side add... View all property information
    Location Information
    Michigan City, Indiana 46360
    5 of 5 stars Reviewed 9 May 2016
    Oustanding little home, very clean and just what we needed. I brought my wife and small children here for 3 nights, and had a fantastic time. Quiet neighborhood, easy parking...
    5 of 5 stars Reviewed 10 October 2015
    We stayed for two nights for a Fall get a way in October. The home was beached themed, well stocked, clean as a museum and quiet. The home sleeps four with all the comforts of...
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    1 / 18
    Long Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • x
    About this property
    Traditional 5 bedroom, 3 1/2 bath Georgian on a a grassed dune. Main floor master suite with gorgeous master bath that has a jetted tub, steam shower & walk-in redwood closet. Breathtaking garden room with vaulted ceiling & loads of light through skylights and walls of windows. Hardwood, tile,... View all property information
    Location Information
    Long Beach, Indiana
    1 / 20
    Michigan City
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • ?
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    • x
    About this property
    Visit this Artsy Cottage Retreat for a great time with your family and friends. This home has 2 baths, one containing a huge private whirlpool tub. Walking into the home you can hang downstairs in the finished cedar family room complete with bar, glass top dining area for 6, sleeper sofa, wrap... View all property information
    Location Information
    Michigan City, Indiana 46360
    1 / 20
    Michigan City
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • x
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    • x
    About this property
    ***Forth of July Week Available*** New luxury lake house available in the beautiful Beachwalk Resort community in Michigan City, Indiana. Home can accommodate up to 16 adults with beds and dining. This home has two master bedrooms – both with king beds and private bathroom. One is on the second... View all property information
    Location Information
    Michigan City, Indiana 46360
    1 / 38
    Michigan City
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • ?
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    • x
    About this property
    Lake Michigan Beach Cottage rental in Beachwalk, Indiana. Sheridan Beach. Stop 7, Lake Shore Drive and Beachwalk Lane. Michigan City, Indiana. Sleeps 8-10 adults. 2 themed bedrooms: The Jungle Room for kids; The Hunting Lodge for adults. Best cottage rental, famous Beachwalk Resort. Steps... View all property information
    Location Information
    Michigan City, Indiana 46360
    1 / 12
    Michigan City
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    RICHIE’S RETREAT About the Rental: Visit this Artsy Cottage Retreat for a great time with your family and friends! Enjoy the sandy beaches or go to the Lighthouse Mall, Bluechip or Four winds Casino's, Hard Rock Cafe, Theaters, Wineries, Breweries, Whiskey Distilleries, Antique Shopping,... View all property information
    Location Information
    Michigan City, Indiana 46360
    1 / 12
    Michigan City
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Internet Access
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    • DVD Player
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This cottage is located in Beachwalk Resort community (tennis, private lake & beach, rental of kayaks, canoes and paddel boards, pool, boat park plus private access to Lake Michigan beach (1 block). Resort feels like Martha's Vineyard. This home features kid friendly amenities (PS2 tons of video... View all property information
    Location Information
    Michigan City, Indiana 46360