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Vacation rentals with a patio in Chesterton

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Top-rated patio rentals in Chesterton

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Home in Chesterton

4.8 out of 5 average rating, 255 reviews

South Shore Studio Apartment {National Park}

I have to warn u 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 11 -8 generely some music playing and musicians are welcome !! if you happen to book on a sunday i host open mic in my Barn every sunday ..... pretty relaxed. Upon arriving turn into the driveway just passed my house and then right into the yard apartment is upstairs the door is open keys inside. ✌️

Guesthouse in Valparaiso

5 out of 5 average rating, 37 reviews

Lake retreat w/ unique dome near Indiana Dunes

Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

Guesthouse in Bridgman

4.93 out of 5 average rating, 129 reviews

The Hideaway Loft, a lovely 1 bedroom apartment.

Get out of town and escape to this unique and tranquil retreat. Juniper's Hideaway Loft is a private 1 bedroom apartment that offers both seclusion and proximity. Just minutes from Weko Beach and Warren Dunes, this is the ideal location for any outdoor enthusiasts. Check out local wineries and breweries, and enjoy the treasures of southwest Michigan from this 9 acre wooded space. The Hideaway Loft in Bridgman offers the perfect weekend getaway, only 90 minutes from Chicago. EV charger onsite!

Home in Michigan City

4.97 out of 5 average rating, 105 reviews

Spacious Superior: The perfect relaxation getaway!

Location, location, location! Unwind & gather with family/friends on a cute, tree-lined street in Michigan City! This large, fully updated home is stocked with new kitchenware, appliances, beach toys/towels, & two smart TVs. Less than 10 minutes from the beach & casino, & a short drive from hiking trails in the nation's newest national park. Enjoy a meal around the farmhouse table, roast a s'more in the firepit, or venture out to explore wineries, cafes, boat rentals, outlet malls, & more!

Condo in Portage

4.94 out of 5 average rating, 114 reviews

Cozy 1 bedroom condo on Marina near Lake Michigan

Come stay at this adorable one bedroom condo on the Marina near Lake Michigan! This condo has everything you need to enjoy a special getaway from everyday life. Conveniently located near the Indiana Dunes with the South Shoreline to Chicago directly across the street. Relax on the patio and enjoy watching the boats come and go as they please. Check out the drinks and food at the Marina Shores Yacht Club just a short walk away from this unit. This condo has everything you're looking for!

Rental unit in Chesterton

5 out of 5 average rating, 26 reviews

Chesterton Charmer: Lower Unit

Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a two-minute walk to downtown Chesterton! Guests will love this upper unit in a historic home. The prime location and fully stocked kitchen allow you to walk downtown for a meal or dine in. Watch a movie in the spacious living room, enjoy a cup of coffee on the cozy porch, or venture out to explore nearby attractions. Whether you want to lay low & relax, or explore all the area has to offer, this rental has you covered!

Cottage in Harbert

4.98 out of 5 average rating, 113 reviews

Hot tub, bikes & close to Cherry Beach in Harbert!

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!

Bungalow in Sawyer

4.99 out of 5 average rating, 194 reviews

The Harbert Bungalow-Hot Tub-Walk to Beach

Welcome to the Harbert Bungalow! Our newly renovated private guest house is located along the Red Arrow Bike path; just a 1 mile walk/bike to Harbert Beach and directly across the street from the Harbert Community Park. Enjoy all Harbor Country has to offer while staying in your own cozy bungalow with a tropical-inspired interior and private luxury outdoor space. Guest will have access to a private gated patio and parking right in front of the house for two vehicles.

Home in Plymouth

4.91 out of 5 average rating, 137 reviews

Plymouth YellowRiver Cottage: Peaceful Community

Whether just passing through or visiting with the whole family…Stay at our cozy home in the heart of downtown Plymouth while enjoying a country-like setting with nearby public access to the Yellow River. The Centennial Park, Magnetic Park and/or River Square Park may provide hours of family enjoyment connecting with the Greenway Trails. The Rees-3 minutes Plymouth Hospital-5 minutes Plymouth Motor Speedway-6 minutes Culver Academies-21 minutes Notre Dame-40 minutes

Home in Chesterton

4.96 out of 5 average rating, 56 reviews

Cheerful two bedroom home downtown Chesterton

The house is located in the charming and walkable downtown Chesterton where you can find restaurants, wineries, breweries and coffee shops. It's a ten-minute drive to the beautiful Indiana Dunes National Park which as fabulous beaches and hiking trails and a newly remodeled Pavillion which houses a restaurant and a rooftop bar overlooking the lake. Weekends between May and October hosts a European Market and Upsadaisy Market (artsy and vintage offerings).

Guesthouse in Valparaiso

4.98 out of 5 average rating, 130 reviews

Cozy Luxe Downtown Valparaiso Stay

Welcome to “Chalet Valpo”! A historic carriage house located minutes from the heart of Valpo that we have had completely gutted and made new for you! This home is a carriage house, it is located on our personal property. You have complete privacy during your stay in a private fenced in area. Do not hesitate to reach out with any questions. Walkable to downtown Valparaiso! NO CLEANING FEE!

Home in Chesterton

4.83 out of 5 average rating, 89 reviews

National Park Nature Lover's Paradise

Nestled on over a half acre and surrounded by Indiana Dunes National Park, our home offers panoramic views of the surrounding forestry. Secluded but only a mile from the South Shore train station with access to Chicago and the National Park Campground. Enjoy the large indoor and outdoor space with friends and family or explore all that the Indiana lake shore and Chicago has to offer.

Vacation rentals for every style

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Hotels

Stylish accommodations and amenities

Popular amenities for Chesterton patio rentals

Free parking on premises

Air conditioning

Apartment rentals with a patio

Rental unit in Near North Side

4.91 out of 5 average rating, 117 reviews

Modern 3BR with Private Rooftop & Free Parking

Rental unit in Lincoln Park

4.84 out of 5 average rating, 249 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

Rental unit in West Lake View

4.93 out of 5 average rating, 138 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Rental unit in Homewood

4.94 out of 5 average rating, 62 reviews

Charming Garden Apartment

Rental unit in Portage

5 out of 5 average rating, 16 reviews

Lake Landing

Rental unit in Andersonville

4.99 out of 5 average rating, 123 reviews

Vibrant & Chic Apt On Quiet St in Andersonville

Rental unit in Evanston

5 out of 5 average rating, 100 reviews

Spacious 3 bdrm apt. near NU + Chicago + lake.

Rental unit in Sawyer

4.88 out of 5 average rating, 98 reviews

Morton's Retreat Cozy 1 Bedroom Apartment

House rentals with a patio

Home in Michigan City

4.84 out of 5 average rating, 117 reviews

The Blue Herron- Dog friendly

Home in Michigan City

4.99 out of 5 average rating, 91 reviews

5 min to beach-zoo-brewery-casino-restaurants

Home in Michigan City

4.94 out of 5 average rating, 108 reviews

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

Home in Osceola

4.91 out of 5 average rating, 105 reviews

Nature Enthusiasts, Private setting/Park Entrance

Home in Three Oaks

4.98 out of 5 average rating, 144 reviews

Casa Gitana - Boutique Style Stay in Three Oaks

Home in Valparaiso

4.99 out of 5 average rating, 72 reviews

Entire Home Downtown Valparaiso!

Home in Michigan City

4.92 out of 5 average rating, 62 reviews

Roomy & Cozy 3 Bd 2Ba just mins from Indiana Dunes

Home in Chesterton

5 out of 5 average rating, 16 reviews

INDIANA DUNES/LAKE MICHIGAN/CHESTERTON HOUSE

Condo rentals with a patio

Condo in Pilsen Historic District

4.86 out of 5 average rating, 116 reviews

816 PiLZeN Luxury | Rooftop | Garage Parking

Condo in Lake View

4.98 out of 5 average rating, 131 reviews

HoIiday Decorated Designer’s Duplex 2bd 2bat

Condo in West Town

4.96 out of 5 average rating, 103 reviews

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

Condo in Lake View

4.98 out of 5 average rating, 103 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Condo in Near West Side

4.86 out of 5 average rating, 122 reviews

Tri-Taylor/Medical Dist. near West Loop

Condo in Ukrainian Village

4.92 out of 5 average rating, 106 reviews

Modern Chicago Movie Themed Apt

Condo in Wicker Park

4.94 out of 5 average rating, 129 reviews

CHIC DOWNTOWN PENTHOUSE w/ private roof +parking

Condo in Lincoln Park

4.74 out of 5 average rating, 284 reviews

Chic Home! Walk to Nightlife-Comedy-Restaurants!

Quick stats about vacation rentals with a patio in Chesterton

Total rentals
40 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
3.9K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

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