Vacation rentals with a patio in Chesterton

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Top-rated patio rentals in Chesterton

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Guest favorite

Condo in Portage

4.94 out of 5 average rating, 67 reviews

Unsalted Stay - Waterfront Condo

Unsalted Stay gives you a central location to all the nearby sites Northwest Indiana has to offer!A cute and cozy waterfront condo that offers full amenities for family fun, major arteries for work and business, and endless adventures! Located on the lovely Marina Shores Harbor, 2 min from the National Lake Front beach,5 min from Indiana Dunes National Park, across the way of the South Shore train line(45 min ride to Downtown Chicago),40 min from New Buffalo Michigan, and 60 min from Notre Dame!

Sep 7 – 14

G$33,375 GYD per night

Guest favorite

Home in Lakeside

4.96 out of 5 average rating, 158 reviews

Adorable couples escape with year-round hot tub!

3 NIGHT MIN JUNE 15 - END OF AUG! ADORABLE HOME IN LAKESIDE WAS RECENTLY REHABBED & OFFERS A SUPER CLEAN AND MODERN FEEL IN THE HEART OF HARBOR COUNTRY. GUEST HAVE ACCESS TO PRIVATE BEACH WHICH IS A 7 MIN WALK AWAY - NO CROWDED BEACHES! YEAR ROUND HOT TUB, A SUPER COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL COMPLETE THIS LOFT LIKE HOME. FULLY STOCKED KITCHEN, HIGH DEF TV, STREAM MUSIC, ETC! YOU WILL LOVE IT!

Nov 23 – 30

G$52,017 GYD per night

Guest favorite

Apartment in Valparaiso

4.94 out of 5 average rating, 17 reviews

The Loft: Stylish Valpo University Extended Stay

The Loft, a BRAND NEW stylish studio in downtown Valparaiso, offers a unique blend of urban charm and modern convenience. It features a kitchen with a dishwasher, perfect for singles or couples, ensuring hassle-free living. Its prime location allows easy access to local cafes, shops, and cultural venues, making it an ideal urban retreat. The Loft's sleek design & thoughtful amenities provide a comfortable and chic living experience in the city's heart. This is the place for EXTENDED stays!

Aug 8 – 15

G$17,716 GYD per night

Guest favorite

Tiny home in De Motte

4.86 out of 5 average rating, 58 reviews

Tiny Home on Organic Veggie Farm

Place yourself right in the beauty of the land and nature in this cozy tiny home at Perkins' Good Earth Farm. The tiny home has a loft bedroom, bathroom with shower and composting toilet, kitchen, sitting area, and deck. You'll be surrounded by organic vegetable fields, 11 acres of woods, walking trails--and within perfect view of both the sunrise and sunset. You'll also have easy access to our farm store where you'll find fresh fruits & veggies, homemade soups & salads and so much more.

Mar 3 – 10

G$15,323 GYD per night

Guest favorite

Condo in Portage

4.96 out of 5 average rating, 78 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!

Mar 10 – 17

G$27,251 GYD per night

Guest favorite

Home in Porter

4.93 out of 5 average rating, 44 reviews

Brand 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.

Dec 14 – 21

G$35,769 GYD per night

Guest favorite

Guest suite in Gary

4.98 out of 5 average rating, 48 reviews

Beachfront- Lake Michigan- 2bd/2bath -Heated Pool

Lake Michigan - Beachfront w/heated in-ground Pool - Indiana Dunes National Park - Private Basement Guest Suite- 2 Bedroom/2 Bathrooms-Newly Renovated and Beautifully Decorated- Heated In ground Pool* Below Deck at Waters Edge has everything you need to have a comfy and relaxing stay with your family or friends. Hiking, Beaches, X-Country Skiing and so much more! Less than an hours drive to Chicago. *Heated Pool Open from Mid-May to Mid Oct. Pool closed until Mid-May 2024.

Mar 1 – 8

G$20,262 GYD per night

Guest favorite

Home in Chesterton

4.95 out of 5 average rating, 37 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).

Dec 6 – 13

G$37,374 GYD per night

Superhost

Cottage in Grand Beach

4.9 out of 5 average rating, 135 reviews

Beachglass Cottage - Family Friendly Kids and Pets

Welcome to our charming village and quirky pet friendly cottage in Grand Beach – the perfect blend of cozy comfort and playful eccentricity! Nestled less than a mile from the shores of Lake Michigan and just a short 5-minute drive to downtown New Buffalo, our cottage is the ideal retreat for families, girls trips, couples get away. Whether you're seeking a relaxing family getaway or a whimsical retreat, Beachglass is the perfect destination.

Jan 13 – 20

G$38,263 GYD per night

Superhost

Home in Valparaiso

4.89 out of 5 average rating, 9 reviews

Serene Settings

An opportunity too good to pass up. Welcome to this lovely manufactured house! This property features three bedrooms, including a queen-sized bed with a walk-in closet, nightstand, lamp, and chair in the first bedroom. The second bedroom has a twin-sized bed, regular closet, bookcase, and light, while the third bedroom includes a twin-sized bed and a lamp. The two bathrooms feature a tub/shower combo, vanity, and mirror.

May 20 – 27

G$31,896 GYD per night

Guest favorite

Cottage in Union Pier

4.98 out of 5 average rating, 149 reviews

Union Pier Cottage—Steps to lake, hot tub, sauna!

Charming modern vintage cottage located steps away from the beach! Sleeps 6 guests with 2 queen beds, 1 king bed, 1.5 bathrooms + a fully private, hot/cold outdoor shower! Huge fenced-in backyard! Washer/dryer. Eat-in kitchen. Heat, A/C. Front & back decks with outdoor seating, fire pit, grill, sauna, hot tub, beach chairs, cooler, and towels. Includes up to 5 parking spots with a 240V outlet for charging.

Sep 5 – 12

G$143,500 GYD per night

Superhost

Home in Michigan City

4.83 out of 5 average rating, 119 reviews

The Elm St. Retreat - A cozy home, all your own

Welcome to the Elm Street Retreat a cozy, and quiet respite from the hustle and bustle of city life. Just an hour away from Chicago, Michigan City has everything you could want for a quick getaway. Shopping outlets, wineries, breweries, and the Indiana Dunes National Park are all a short drive away. The neighborhood is quiet and safe. Book the Elm Street Retreat for a restful, and quaint stay.

May 26 – Jun 2

G$30,397 GYD per night