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Pet Friendly Holiday Rentals in Chesterton

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    Don't let other travellers get your favourite Chesterton area holiday 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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    The following rentals are within 25 kilometres of Chesterton.
    Gary
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Gary
    6 Bedrooms, 5 Bathrooms, Sleeps 29 Quick View
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    Beautiful apt. across from Lighthouse Mall1 / 13
    (13)Excellent
    Michigan City
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Gary
    6 Bedrooms, 4 Bathrooms, Sleeps 30 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ONLY Luxury Elite Vacation Rental in Indiana as rated by Andrew Harper, LLC, the premier luxury travel rating service! Villa Santorini, only 40 minutes from Chicago, sits atop a 60 ft private dune, borders the IN Dunes National Lakeshore, and has direct beach access. This 6000 sqft year-round...
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    Gary, Indiana 46403
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 30
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    Gary
    4 Bedrooms, 4 Bathrooms, Sleeps 19 Quick View
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    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 5000 sqft Main House at the Miller Beach Dream Retreat is a Five-Star luxury oasis, only forty minutes from Chicago, is a private, secluded, spa-quality, ultimate beachfront getaway right on the Indiana Dunes National Lakeshore. This year-round Beach Retreat is one of the most luxurious...
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    Gary, Indiana 46403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 19
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    Gary
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Miller Beach Dream Retreat Guesthouse is a private, year-round, beachfront getaway right on the Indiana Dunes National Lakeshore and only forty minutes from Chicago. * Open floor plan with Great Room and Kitchen, dining for 6, bath with jetted tub, private entrance and deck with Weber grill *...
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    Gary, Indiana 46403
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Portage
    9 Bedrooms, 6 Bathrooms, Sleeps 42 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Santorini and the newly completed Addition offer nearly 8000 sq ft of luxury living space including 9 bedrooms and 6 baths, 5000 sq ft of outdoor living, 5 wet-bars, 3 wood-burning stoves (seasonal) and premium accommodations for up to 42 guests. Villa Santorini, the ONLY Luxury Elite...
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    Portage, Indiana 46403
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 42
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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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    • Hot Tub
    • Grill
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 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 23 June 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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    Valparaiso, Indiana 46383
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Indiana Dunes Beach Getaway Home1 / 34
    (1)Excellent
    Lake Station
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Washer
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2018
    The house was in excellent condition with great amenities. Just five minutes from the beach and 20 minutes from outlet mall and Bass Pro Shop.Comfortable beds and plenty of...
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    About this property
    Indiana Dunes Beach Getaway Home Walk to the beach or just relax in our comfortable home. Property has 4 bedrooms and 2 bathrooms, 2 family areas, and a large dining room table great for conversations with friends and family and dinner time. Private back yard with a fire pit and chairs and a grill...
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    Lake Station, Indiana 46403
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Across from the pool & Dog Friendly1 / 24
    (1)Excellent
    Michigan City
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2017
    This home provided a great location for the whole family. Four generations and all found something to do. The location was surrounded by great places to visit and memories to be...
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    About this property
    Vacation Station, located right across from the pool house and Lake Kai offers large gathering space along with huge screened wrap around porches w/ plenty of seating. The main level has a large living room, dinning room and kitchen w/ open concepts and plenty of seating at the large table and...
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    Location Information
    Michigan City, Indiana 46360
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Il Giardino1 / 18
    (1)Very good
    Michigan City
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Garden
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2017
    Great week in Michigan City visiting with friends and relatives. This location was perfect with easy access to everything we wanted to do and see. Owner was easily to work with...
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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...
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    Michigan City, Indiana 46360
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gary
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Terrace
    • Private Garden
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for walking and hiking in the dunes and on the beach. Watch the woods from the screened in front porch. Great wood stove . 5 minute walk from semi-private Lake Michigan beach and 45 minutes from downtown Chicago. The house, is built into dunes so most of the living space is on second floor...
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    Location Information
    Gary, Indiana 46403
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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