
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.

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes
Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

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. ✌️

UncleLarrysLakePlace HotTubKayaksPingPong
A tribute to our favorite world traveler-he's the first to stay at our properties and give us the good, bad and ugly so we can fine-tune the ultimate experience for YOU. This newly remodeled lake home boasts 4 sleeping areas, year-round hot tub, game room with a ping pong table and large screen TV, large gathering spaces in and out, new kitchen and your own kayaks to explore the area. Enjoy sunsets and lake views from the hot tub on the expansive deck or while grilling on the Weber gas grill.

Lake Trail Cottage
Located just 1 mile from Lake Michigan. Lake Trail Cottage is the closest home in Pines and just minutes from Beverly Shores beaches! The cottage has two bedrooms one bath. With basement Rec room. Home sleeps 7. The primary bedroom features a Queen bed, 42in Smart TV. The second room has a full size bed. Pullout couch/ living room. Calumet Trail and South Shore Train (Chicago)is located directly behind home. South Shore train to Chicago is 1 mile from house. Bikes & beach supplies included.

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.

Hot tub open year round in modern/rustic cottage!
Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

Visit Lake Michigan | Perfect Couple's Retreat
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!

King Bed Retreat, Minutes to Beach & Dunes
Escape to the Hoosier Hideaway, a newly renovated 2-bedroom cozy retreat in a vibrant, walkable Michigan City neighborhood. Blending vintage 1949 charm with modern comforts like a 70" TV and electric fireplace, this ground-floor unit is perfect for families, weekend explorers, and traveling professionals. Enjoy easy access to local dining, Lake Michigan, and the Indiana Dunes. Comfortably accommodates 4-6 guests.
Popular amenities for rentals with patio in Chesterton
Flat rentals with a patio

Beachside Top-Floor Apt | Steps to Lake Michigan

The Moroccan Hideaway

The Sunshine House: Scenic Skies Unit!

Lakeview Suite

Chesterton Charmer: Lower Unit

Morton's Retreat Cozy 1 Bedroom Apartment

Lovely 1 bed room apartment, all to yourself.

Creekside Cozy 3BD • Near Dunes or Corporate Stay
House rentals with a patio

Jefferson

Modern House, Sleeps 10, Near Downtown, 2000 sqft

The Ashlin House.

Lux home, sauna, hot tub, firepit, 5 min to beach

Pet Friendly, Fenced Yard, and Hot Tub Getaway

Beach! Hot Tub! New Buffalo! Firepit! King Bed!

Indiana Dunes, Beach, Chicago, Shopping Center

Designer's Own Cozy Cottage
Apartment rentals with a patio

South Shore Dr Retreat

Updated Cottage Downtown, walk to Beach

Spacious Chicago South Side Condo

Waterfront 2 BR Apt, 3 mi. to ND

ND Events or Business Short Stay Modern Condo

UChicago Condo | 2 Baths, Private Parking & Entry

Live the marina life in New Buffalo!

The ModernFarmhouse Chicago-Near Downtown Chicago
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $181 SGD | $177 SGD | $176 SGD | $167 SGD | $207 SGD | $218 SGD | $236 SGD | $251 SGD | $205 SGD | $194 SGD | $192 SGD | $182 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 $103 SGD per night before taxes and fees

Verified guest reviews
Over 4,590 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
30 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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- Rentals with a patio Porter County
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- Rentals with a patio United States
- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- Warren Dunes State Park
- 875 North Michigan Avenue
- Indiana Dunes State Park
- University of Notre Dame
- Shedd Aquarium
- The Field Museum
- Humboldt Park
- Chicago River Walk
- University of Chicago
- SeatGeek Stadium
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Union Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory





