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Chesterton Holiday Vacation with Pools

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    C$585 Average
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    Don't let other travellers get your favourite Chesterton area vacation rental. You're so close to securing your perfect getaway. Book today.
    12 Matching Rentals in the Chesterton AreaView all 78 rentals
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    5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool1 / 16
    (1)Excellent
    Chesterton
    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    The following rentals are within 25 kilometres of Chesterton.
    Southern Belle1 / 14
    (7)Very good
    Michigan City
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    My Blue Heaven1 / 22
    (2)Very good
    Michigan City
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Mint Julep1 / 9
    (5)Very good
    Michigan City
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2017
    The home was cozy. The community is family friendly, and has all of the classic summer amenities. My daughter, her friends, and many other kids found the smooth community drive...
    Reviewed June 25, 2017
    Very clean with nice finishes, and perfect size for my teen and I. I didn't see photos of the master bath, but upon arriving was pleasantly surprised that it had been recently...
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    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,...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Blueberry Cottage1 / 11
    (4)Excellent
    Michigan City
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Children's Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 22, 2017
    The blueberry cottage is the perfect getaway from the everyday! Close by to so many fun activities! Affordable and beautifully maintained property in Beachwalk!
    Reviewed September 25, 2016
    We loved staying in the beautiful Blueberry Cottage! Matt was very helpful answering all our questions about the area, bike trails, distance to the beach, and train schedules to...
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    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...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Moondance--Huge Open Concept in Central Beachwalk1 / 36
    (17)Excellent
    Michigan City
    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Children's Pool
    • Wi-Fi
    • DVD Player
    • Washer
    • Housekeeping Included
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Group of retired friends recently spent a wonderful week at Moondance. Comfortable beds, great open area to relax, well equipped kitchen, and easy access to shopping and other...
    Reviewed 3 weeks ago
    In warm weather the beech is close and the pool is beautiful. On cooler days the shopping mall and cute town are close by. The condo itself is well appointed and spotlessly...
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    About this property
    Located in the acclaimed Beachwalk resort community in the Indiana Dunes on Lake Michigan, just one hour from Chicago, this house ('Moondance') and its perfect central location is a Beachwalk favorite. Unique among Beachwalk homes, Moondance has an open floor plan with a stunning cathedral ceiling...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    Sun King--Brand New 6th Full Bathroom!--Huge Beautiful Home1 / 39
    (19)Excellent
    Michigan City
    7 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Children's Pool
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 27, 2018
    I'm not much of a review guy, but I felt compelled to do so with this place. My family and 3 others ( a total of 8 adults & 10 kids) decided to get away for a weekend, so I...
    Reviewed September 24, 2018
    This is the second year my family, friends and I have booked this home in Beachwalk. We cannot say enough wonderful things about the space, as there is plenty of room to move...
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    About this property
    Beachwalk Resort is an award winning beach community located right next to the Indiana Dunes National Lakeshore on one of Lake Michigan's most beautiful stretches of beach. Sun King, and the included coach house The Jester, combine to create one of Beachwalk’s largest properties, complete with 7...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 24
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    Guest House in Private Gated Nudist Community1 / 2
    (2)Excellent
    Valparaiso
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2017
    Let me start off by saying this is a great place to come if you're a first timer. The wife was a little apprehensive about being nude around other people ,but she warmed up...
    Reviewed June 22, 2017
    I have visited numerous other nudist communities but Lake of the Woods Club was by far the best. The guest house we stayed in had everything we could have wanted, and the hosts...
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    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...
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    Location Information
    Valparaiso, Indiana 46383
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Michigan City
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A spacious main floor with open kitchen, dining area and living room with access to the screened porch to extend your space even further. Dining table seats 6 with an additional 4 stools at the kitchen island extending your dining seating to 10. The second floor hosts 3 of the 5 total bedrooms....
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    The Queen Bee--Beachwalk's Favorite Large Home Rental1 / 42
    (9)Excellent
    Michigan City
    7 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Patio
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 9, 2017
    We have rented before from the same owners(Sun King) and this property too surmounted our expectations! The owners are very easy to work with and very accommodating! Amazing...
    Reviewed October 27, 2016
    Wonderful place for a large group. The kitchen table was awesome to gather around for games and meals. Had everything we need and more. Would definitely return.
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    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...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 24
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    Michigan City
    9 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Patio
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Restored in 2018, this impressive home is the ideal space to have some rest and relaxation with friends and family. With a quick 3 minute walk to Sheridan beach and a private in ground pool, you'll never want to leave! This home includes 4 queen beds, 3 full size beds, 6 twin beds. Maximum of 20...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 9 Bedrooms, 5 Bathrooms, Sleeps 20
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    Michigan City
    8 Bedrooms, 6 Bathrooms, Sleeps 27 Quick View
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    Amenities & Details
    • Children's Pool
    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Poseidon is a brand new Beachwalk listing and it is Beachwalk's largest home. The new owners poured their money and energy into turning this home into Beachwalk’s premier property. This listing continues to be updated with new photos as work is completed. Poseidon and Trident, the included coach...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 27
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