
Holiday rentals with a patio in Chesterton
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Top-rated rentals with patio in Chesterton
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

Steps from the beach and a mile from National Park
Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

Cozy Log Cabin Near Indiana Dunes & Lake Michigan!
Less than 10 minutes from Indiana Dunes National Park and Lake Michigan, our beautiful log cabin sits on 2 acres while still being in the heart of Portage! Our large front deck overlooks state land giving a beautiful, private view out of our large windows. Our cozy cabin has 3 bedrooms and 3.5 bathrooms with fun, thoughtful touches for your family including video game consoles, movies, books, a LOT of games, a pool/ping pong table, 2 fire pits, and more! Age limit: 25+ years old Sorry no pets

Beachfront- Lake Michigan-Hot Tub-Heated Pool
Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

South Shore Studio Apartment {National Park}
I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

Casa Gitana - Boutique Style Stay in Three Oaks
Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

Indiana Dunes, Beach, Chicago, Shopping Center
Near Indiana Dunes, Lake Michigan and Chicago when you stay at our centrally-located townhome. For family fun we’re is located a few minutes away from the shopping center, plenty of restaurants, main chain stores and more. Enjoy the convenience a parking garage& driveway, outdoor patio, dishwasher and washer & dryer. home has 4 beds 2 bedrooms. One bedroom has a Queen bed, second bedroom has a Queen bed and a Full bed. The Living room has a sofa bed. Shovel in the garage for when it snows.

New Dunes Escape
Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

Visit LakeMichigan Beach-Brewery-Casino-OutletMall
Explore the beautiful Indiana Dunes National and State Parks. Book your stay at this cozy, newly renovated 2 bedroom home centrally-located for all your adventures. Within 2 miles of beach, restaurants, brewery, winery, casino, concert venue, spa, botanical garden, boat tours, kayak rental. Bonus trip: take the Southshore commuter train to Chicago for the day. Here, you can explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. 💙

The Dune Den! Huge Yard/Firepit/Near Town+Dunes
Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Welcome to Blue Buff! Pet Friendly/Firepit/Fenced!
Enjoy this nicely appointed 3 bed/2 bath. Spacious kitchen open to comfy living room. Basement houses a comfy rumpus room. Have fun playing board games, watching tv, & games like Jenga, checkers. Enjoy the fenced yard, playing bags & putting green, grill, & firepit after you come home from a day of touring wineries/breweries, shopping in the local stores, galleries, antique stores, & casinos. Noise machines provided. Pet fee $150 flat, 2 pet max. License # Cr230049

The Sunshine House: Scenic Skies Unit!
✨ Location, location, location! ✨ The Scenic Skies Unit is a cheerful second-floor apartment in the historic Sunshine House, featuring bright décor, a comfy queen bed, and all the essentials for a relaxing stay. Guests can cook in the stocked kitchen, roast s’mores around the shared fire pit, or walk downtown to the outlet mall, restaurants, and beaches. Perfect for up to 6 guests looking to relax and adventure in Michigan City!

The Lake Escape - 5 Mins from beach, casino, & zoo
LOW CLEANING FEE! Stay close to the beach, only 1.3 miles away, at our spacious property in Michigan City, Indiana! Luxury amenities include: a large jacuzzi tub, dual shower heads for up to 2 person showers, urinal, a large king size suite with a 65 inch TV, and more! We’re located on 11th St. That means that the South Shore train line runs right in front of our home! It is a no horn zone.
Popular amenities for rentals with patio in Chesterton
Flat rentals with a patio

Beachside Top-Floor Apt | Steps to Lake Michigan

The Moroccan Hideaway

Chesterton Charmer: Lower Unit

Morton's Retreat Cozy 1 Bedroom Apartment

The Loft at the Acorn Theater

Creekside Cozy 3BD • Near Dunes or Corporate Stay

King Bed Retreat, Minutes to Beach & Dunes

Holiday Haven: King Beds, Fire Pit, 7 min to beach
House rentals with a patio

The Blue Herron- Dog friendly

The Guesthouse

The House Near The Lakes

Lake Trail Cottage

Life's A Beach! Relaxing ranch close to beach!!!

2 bedroom 2 bathroom home away from the noise.

UncleLarrysLakePlace HotTubKayaksPingPong

Vale Cottage: Premium 2BR, downtown Valpo
Other holiday rentals with a patio

South Shore Escape

DuneHouse Miller Beach - 1.5 blocks to beach

Chic Beach Home | Walk to beach, zoo & park!

Cozy Mid-Century Home•Private Pool• Dog-friendly!

Cozy Haven ~Modern Cottage in woods close to Dunes

Family Friendly 4 bd Home

Woodland Cabin Escape, walk to Lake Michigan

Aviation Getaway with Private Runway Access!
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $144 SGD | $177 SGD | $163 SGD | $165 SGD | $205 SGD | $217 SGD | $235 SGD | $249 SGD | $204 SGD | $192 SGD | $191 SGD | $181 SGD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals with a patio in Chesterton

Total holiday rentals
Explore 40 holiday rentals in Chesterton

Nightly prices starting at
Chesterton holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 4,510 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Chesterton holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterton rentals

4.8 Average rating
Chesterton stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Rentals with a firepit Chesterton
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- Pet-friendly rentals Chesterton
- Family-friendly rentals Chesterton
- Rentals with outdoor seating Chesterton
- Rentals with a washing machine and dryer Chesterton
- House rentals Chesterton
- Rentals with a patio Porter County
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- Rentals with a patio United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Warren Dunes State Park
- The Field Museum
- Guaranteed Rate Field
- Wicker Park
- Lincoln Park Zoo
- University of Notre Dame
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- University of Chicago




