House vacation rentals in Chesterton

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Top-rated house rentals in Chesterton

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Guest favourite

Home in Michigan City

4.94 out of 5 average rating, 401 reviews

Small Clean Home Near Beach, Casino, Outlet Mall

This cozy, clean home is located 2.9 miles to Beach, Outlet Mall, and Casino. Quiet neighborhood. Well maintained property. Perfect for a couple or business traveler. It is not child proof. It is not suitable for small children. There are open stairs that cannot be blocked. We do not accept pets. I have an autoimmune disease. I am allergic to pet dander We request drivers license of each guest. Per Airbnb guidelines I am disclosing we have cameras on exterior north/east of home with audio.

Sep. 19 – 26

$194 CAD per night

Guest favourite

Home in Michigan City

4.96 out of 5 average rating, 217 reviews

Cozy House near Beach, Casino, Outlets, & Hiking

Escape with family or friends near the dunes of Lake Michigan! Recently renovated and decorated, you won't find a better rental! Guests will love this cozy home located near a variety of attractions. Just 2 miles from the sandy beaches, near tree-lined hiking trails in the nation's newest national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops. This is the perfect little getaway for up to 6 people who want to relax or adventure!

Mar. 14 – 21

$280 CAD per night

Guest favourite

Home in Valparaiso

4.95 out of 5 average rating, 112 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

Pontoon INCLUDED in all rentals Now-September 30, 2024 No extra fees for unlimited use of private pontoon, pier, paddle boards and more!! Rental price of our lakefront house includes the pontoon, deck, yard and endless activities!! Take the pontoon for a cruise, fish, swim, paddle board, kayak, watch the wildlife or have a bonfire!! Travel 15 minutes to the Indiana Dunes or 10 minutes to downtown Valpo. You will also be able to cook delicious meals on the propane grill & fully stocked kitchen

Aug. 11 – 18

$876 CAD per night

Guest favourite

Home in Portage

4.92 out of 5 average rating, 149 reviews

Newly Renovated with Finished Basement

This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

Nov. 19 – 26

$270 CAD per night

Guest favourite

Home in Michigan City

4.96 out of 5 average rating, 193 reviews

Pottawattamie Place - near Dunes, Beach, & Casino

Escape with family & friends near the dunes of Lake Michigan! You'll love cozy "Pottawattamie Place," located near a variety of attractions. Fully loaded kitchen, backyard firepit, foosball, & fun! Walk to Pottawattamie Park or drive 3 short miles to the sandy beaches. Near tree-lined hiking trails in the nation's newest national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops. Perfect for those who want to relax AND adventure!

Jan. 5 – 12

$235 CAD per night

Guest favourite

Home in Michigan City

4.98 out of 5 average rating, 230 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum during our high season (mid May-mid September), and open 2 night stays the week prior if we have a couple open days.

Sep. 3 – 10

$326 CAD per night

Guest favourite

Home in Michigan City

4.92 out of 5 average rating, 205 reviews

✦Cozy Bungalow✦ Central location, 2.4mi to Beach

Relax in our charming & cozy bungalow close to beach, hiking trails, breweries, & conveniences like restaurants & grocery stores. A great getaway year-round. 20 mins to cross-country ski trails at the State Park! 2.4 miles from Lake Michigan to enjoy a day at the beach. 2 miles to Outlet Mall and Casino. 3 miles to Mount Baldy & Indiana Dunes National Park to explore 50mi of dunes, beaches, wetlands, prairies, rivers & forested trails. Perfect hub for a day trip to Michigan or South Bend!

Sep. 30 – Oct. 7

$233 CAD per night

Guest favourite

Home in Michigan City

4.96 out of 5 average rating, 107 reviews

Midcentury marvel steps from beach! Pups

Year-round beach fun an hour from Chicago!Welcome to Barefoot Bungalow, a mid-century marvel with modern amenities. Your group will love the game room with pool table, ping pong. Private dog-friendly fenced backyard with grill, patio & firepit. Short stroll to Stop 7 to beach (Beachwalk boardwalk, wagon provided). Quiet relaxation far from the madding crowds. So many excellent restaurants, shopping, brew pubs, wineries, hiking, biking. Off-street parking, Wave bus

Sep. 28 – Oct. 5

$276 CAD per night

Guest favourite

Home in De Motte

4.96 out of 5 average rating, 207 reviews

Country Cottage

Looking for week-end get away? Traveling through Northwest Indiana on I-65 and looking for a quiet place to stay for the night? Situated on 6 acres and with convenient (2 mile) access to I-65, our cozy Country Cottage is a great choice! Enjoy the cottage feel of this recently renovated (new cabinets, flooring, appliances) and charmingly decorated home, located in close proximity to local attractions! Our 650 square foot cottage is ideal for 1 - 4 guests.

Mar. 6 – 13

$169 CAD per night

Guest favourite

Home in Beverly Shores

4.97 out of 5 average rating, 187 reviews

Secluded Modern Retreat Near Beach - "Sandlot"

Stunning modern home overlooks private sand dunes on 5 wooded acres just a mile away from beautiful Lake Michigan beaches and surrounded by the Indiana Dunes National Park. Relax in our updated open-concept unique home nestled in the dunes. Enjoy the trails in the backyard, the friendly community, and local attractions near by. Just an hour to Chicago by car or the South Shore train is 1/2 mile from the house, with easy rides to Chicago and South Bend.

Dec. 15 – 22

$742 CAD per night

Superhost

Home in Porter

4.82 out of 5 average rating, 154 reviews

Modern Indiana Beach Home Near Lake Michigan

This Porter Indiana beach house is a modern craftsman style home in the Dunes! Featuring an open floor plan, this heavily renovated home is the perfect place to spend your next getaway, whether you just want to retreat to write a book, relax with friends or family, or spend your days by the water! It is 3 beds, 2.5 baths, is completely updated and it is a quick drive, walk or bike ride to the Indiana Dunes National Lakeshore + Porter Beach!

Apr. 2 – 9

$415 CAD per night

Guest favourite

Home in Chesterton

4.98 out of 5 average rating, 126 reviews

Hotel Whiskey

Fully remodeled and tastefully decorated two bedroom home for short or long term stays. Office space for work travelers. Pet friendly with secure fenced in back yard. Walking distance from downtown with quaint shops, wine bar, craft beer bar, restaurants and bike trails. Whether you're in town for work, visiting family or just looking for a weekend getaway, this house and location are perfect for short or long term stays.

Feb. 1 – 8

$289 CAD per night