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Vacation Rentals in Chesterton, IN and nearby

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    All 26 Rentals in the Chesterton Area
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    From
    $799
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    1 / 16
    Chesterton
    5 Bedrooms / 3 Bathrooms / Sleeps 20
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    $550
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    1 / 40
    Chesterton
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    The following rentals are within 15 miles of Chesterton, Indiana.

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    1 / 14
    5 of 5 stars (5) Excellent
    Michigan City
    1 Bedroom / 1 Bathroom / Sleeps 3
    travelers have booked this property
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    1 / 17
    4.5 of 5 stars (2) Very good
    Michigan City
    1 Bedroom / 1 Bathroom / Sleeps 3
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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. Wonderful location right across the street from the Lighthouse Mall. You can walk to the Lighthouse Mall, Uptown Art District, restaurants, coffee... View all property information
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    4 of 5 stars Reviewed July 10, 2014
    The apartment was easy to find and located directly behind the outlet mall. The beach and main street area were within walking distance, had we chosen to do so. We found...
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    $350
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    1 / 28
    5 of 5 stars (5) Excellent
    Michigan City
    6 Bedrooms / 3 Bathrooms / Sleeps 16
    travelers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Located in the acclaimed Beachwalk resort community in the Indiana Dunes off of Lake Michigan, this house ('Moondance') and its perfect central location is a Beachwalk favorite. Unique among Beachwalk homes, Moondance has an open floor plan with massive cathedral ceilings perfect for hosting... View all property information
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    5 of 5 stars Reviewed October 22, 2014
    This was my family's first time renting a vacation home and we may never rent anywhere else. We shared this house with another family with a total of 4 adults and 7 kids ages 10...
    5 of 5 stars Reviewed March 31, 2014
    Everything that is advertised about the house is absolutely true except it doesn't include how accomodating and wonderfully caring the owner of the house is! We were all so very...
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    1 / 11
    5 of 5 stars (2) Excellent
    Michigan City
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Charming upstairs apartment. Has a full kitchen, dishwasher, breakfast bar, queen size bed etc. Wonderful location right across the street from the Lighthouse Mall. You can walk to the Lighthouse Mall, Uptown Art District, restaurants, coffee shops, library, the Saturday Farmers Market, and... View all property information
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    5 of 5 stars Reviewed July 26, 2013
    Wow!! Beautiful updated apartment with large rooms and a full new kitchen within walking distance to restaurants, shops and the beach. Amazingly quiet at night. The owner was very...
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    $130
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    1 / 15
    4.5 of 5 stars (3) Very good
    Michigan City
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Wonderful location right across the street from The Lighthouse Outlet Mall. Walk to restaurants, shops, beach, art district and the Zoo. 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. View all property information
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    4 of 5 stars Reviewed September 21, 2014
    We stayed with 2 Persons in the apartment for 11 nights and it was comfortable. It was fully equipped as promised and had enough space to put our own belongings away. Air...
    5 of 5 stars Reviewed July 2, 2014
    From start to finish, this was truly the most lovely experience I have ever had with a vacation rental. Darlene kindly offered an upgrade to this lovely two bedroom - to...
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    $450
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    1 / 35
    5 of 5 stars (3) Excellent
    Michigan City
    7 Bedrooms / 5 Bathrooms / Sleeps 24
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Housekeeping...
    • Internet Access
    • Pool Table
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    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
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    5 of 5 stars Reviewed March 26, 2015
    Our family stayed at Sun King this January with a few other friends and their families. We knew Beachwalk is great in the summer---but, wow, we were blown away by how much fun we...
    5 of 5 stars Reviewed March 18, 2015
    We met up with a few of our friends with young families for a long weekend. It is a very cute place, smartly painted. There is a huge walk around porch when you go through the...
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    $189
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    1 / 20
    Michigan City
    2 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovely cottage that is far larger than it appears. A charming living area has a cozy firepalce and opens to a screen porch. Master suite has queen bed, attached full bath and laundry. Twin daybed (opens to a King size bed)on the second floor and a full-bottom/twin-top bunk finish off the loft.... View all property information
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    1 / 15
    5 of 5 stars (2) Excellent
    Valparaiso
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Peace and Tranquility. This comfortable property is nestled in the center of a 30 acre hardwood forest. It is a perfect place to get away and unwind! The 1500 sq. ft. house offers an antique/ shabby chic furnished, open-air relaxing space inside and out. The upper level rental includes: 2... View all property information
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    5 of 5 stars Reviewed November 10, 2014
    This is a wonderful retreat -- located just minutes from Valparaiso to the South, Chesterton and Lake Michigan to the North. The great room and kitchen are expansive and...
    5 of 5 stars Reviewed June 4, 2014
    The home was very nicely equipped with everything that you would need. We stayed for 11 nights and 12 days and the home came with everything that we would need. Mitch and Kim were...
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    $650
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    1 / 14
    4 of 5 stars (1) Very good
    Michigan City
    5 Bedrooms / 4 Bathrooms / Sleeps 14
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    4 of 5 stars Reviewed January 2, 2015
    Great place for Christmas visit with kids and grandkids. Lake and dune hikes, playground, Christmas decorations. Easy checkin and checkout.
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    $200
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    1 / 9
    Michigan City
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    $325
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    1 / 13
    Michigan City
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The name states it all – Slow down and enjoy a different pace of life on the easy side of the lake! There are plenty of grander, newer homes at Beachwalk, but if you’re looking for a cozy, comfy, quirky little place that you can quickly call home, then Terrapin is the place for you! At Stop 7 on... View all property information
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    $425
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    1 / 13
    Michigan City
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located centrally in the award winning Beachwalk Resort and includes all of the resort amenities including the pool, tennis court, basketball court and the park. Walking distance to Sheridan Beach, many say Lake Michigan's most beautiful beach. You are sure to enjoy the large enclosed porch,... View all property information
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    $299
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    1 / 20
    Michigan City
    3 Bedrooms / Sleeps 10
    traveler have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Kid friendly home featuring Teragren Strand Oriented Bamboo flooring (same flooring in the museum of Science of Industry's Smart Home), stainless steel appliances, reclaimed barnwood table, screened porch with swing and dining area, a sealed gas fireplace, vaulted ceiling, quartzite countertops and... View all property information
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    $225
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    1 / 21
    Michigan City
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    travelers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Recent update includes New comforters, lamps, painted in the kitchen/hallway, main level bathroom, living room and dining room. Blue ray/DVD Player added. Enter in through the screened in porch into the large living area with vaulted ceilings, fire place, flat screen TV and Wifi. Head around... View all property information
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    $350
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    1 / 17
    Michigan City
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    travelers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • 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
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    1 / 13
    Beverly Shores
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Located in the sand dunes, a block and a half from the sandy beaches of Lake Michigan and over 22 miles of State and National Lakeshore. This luxury class, renovated, two-story home offers 3400 square feet of 'International Style' living. Situated on a half-acre wooded lot, the home offers privacy... View all property information
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    $395
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    1 / 29
    Long Beach
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ping Pong Table
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    $105
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    1 / 5
    4.5 of 5 stars (5) Very good
    Michigan City
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    5 of 5 stars Reviewed July 23, 2013
    This is a great little one bedroom with a nice stocked kitchen incl coffee maker and coffee grinder. We came for a couple of nights and went to the beach two days and drove into a...
    5 of 5 stars Reviewed July 22, 2013
    Charming affordable and convenient cottage sits in a quite neighborhood with all the amenities. On foot we where about 3 blocks Lake St. to Lake Shore Dr. to Sheridan Beach...
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    1 / 4
    5 of 5 stars (2) Excellent
    Beverly Shores
    6 Bedrooms / 5 Bathrooms / Sleeps 19
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    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    DunesWalk Inn - A renovated 1881 Mansion now a 5 room boutique hotel/vacation rental property situated in the Indiana Dunes just minutes from beautiful Beverly Shores Beaches. Retreat, Relax, Renew at DunesWalk Inn at the Furness Mansion. Situated on nearly 4 acres, DunesWalk Inn brings modern... View all property information
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    5 of 5 stars Reviewed July 25, 2012
    This is actually the second time we have stayed here and the whole experience has made me put pen to paper (or keyboard). The whole booking process was seamless and the manager...
    5 of 5 stars Reviewed April 27, 2011
    DunesWalk Inn is a novel concept, combining a boutique hotel with a vacation rental. The place is beautiful - the attention to detail and craftsmanship is everywhere. And, the...
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    1 / 12
    Michigan City
    3 Bedrooms / 2 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    $357
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    1 / 18
    Michigan City
    5 Bedrooms / 5 Bathrooms / Sleeps 14
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    $486
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    1 / 38
    Michigan City
    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    1 / 14
    Michigan City
    4 Bedrooms / 3 Bathrooms / Sleeps 16
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    $286
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    1 / 12
    Michigan City
    2 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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