Chesterton Vacation Rentals

Aurora Rossi

Are you in a hurry?

Here is a quick list of Vacation Rentals in Chesterton, selected based on their rating

Name of hotel Accommodation Rating Price, $
Your Midwest Dunes Vacation Tri-State Paradise!

9.7 / 10

(9 Reviews)

From 228$
Blue Birdhouse - Indiana Dunes - Pet Friendly

9.3 / 10

(35 Reviews)

From 139$
Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms

8.1 / 10

(27 Reviews)

From 148$
Roomy Retreat-Family & Friends 2 King Bed Game Room

8.3 / 10

(7 Reviews)

From 472$
Pulaski Point Properties

9.7 / 10

(149 Reviews)

From 53$

Chesterton, Indiana, is a charming town that offers a diverse range of vacation rentals perfect for your next getaway. From cozy cabins to spacious family homes, this destination accommodates various preferences and budgets. Many properties are conveniently located near local attractions, beautiful parks, and the stunning shores of Lake Michigan. Whether searching for a romantic escapade or a family retreat, Chesterton's offerings will surely meet your needs.

Best Chesterton Vacation Rentals

Table of contents

Your Midwest Dunes Vacation Tri-State Paradise! Blue Birdhouse - Indiana Dunes - Pet Friendly Heart Of Indiana Dunes National Park With Hot Tub Charming Chesterton Home: W/ Idyllic Location! Moody Modern Dunes Hot Tub Beach And Trails Sugar Shores ~ 3 Mi To Indiana Dunes Nat'L Park Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms Roomy Retreat-Family & Friends 2 King Bed Game Room Pulaski Point Properties Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts

View all photos

9.7
Excellent
9 Reviews

Your Midwest Dunes Vacation Tri-State Paradise!

📍 1541 Eagle Street

From 228$

Check Availability

View all photos

9.3
Excellent
35 Reviews

Blue Birdhouse - Indiana Dunes - Pet Friendly

📍 5 West Beam Street

From 139$

Check Availability

View all photos

10
Excellent
2 Reviews

Heart Of Indiana Dunes National Park With Hot Tub

📍 1835 Riverline Drive
Check Availability

View all photos

10
Excellent
1 Reviews

Charming Chesterton Home: W/ Idyllic Location!

📍 402 E Morgan Ave
Check Availability

View all photos

10
Excellent
3 Reviews

Moody Modern Dunes Hot Tub Beach And Trails

📍 1724 Tower St
Check Availability

View all photos

10
Excellent
3 Reviews

Sugar Shores ~ 3 Mi To Indiana Dunes Nat'L Park

📍 803 S Calumet Rd
Check Availability

View all photos

8.1
Very good
27 Reviews

Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms

📍 105 West Michigan Avenue

From 148$

Check Availability

View all photos

8.3
Very good
7 Reviews

Roomy Retreat-Family & Friends 2 King Bed Game Room

📍 130 Washington Avenue

From 472$

Check Availability

View all photos

9.7
Excellent
149 Reviews

Pulaski Point Properties

📍 3936 North Pulaski Road

From 53$

Check Availability

View all photos

9
Excellent
352 Reviews

Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts

📍 3558 North Wilton Avenue

From 82$

Check Availability

View all photos

8.2
Very good
512 Reviews

5430 Happy Home

📍 5430 South Dearborn Street

From 51$

Check Availability

View all photos

9.3
Excellent
227 Reviews

2F Chicago'S Little Italy Near West Loop & Downtown

📍 1506 West Polk Street 3F

From 215$

Check Availability

View all photos

9.6
Excellent
129 Reviews

The Avondale Guesthouse

📍 2973 North Elston Avenue

From 240$

Check Availability

View all photos

9.7
Excellent
59 Reviews

Irving Park Updated Vintage Top Unit 2-Flat

📍 4036 North Saint Louis Avenue

From 124$

Check Availability

View all photos

9.2
Excellent
144 Reviews

Lincoln Park 3 Bedroom Penthouse

📍 2633 North Sheffield Avenue

From 234$

Check Availability

View all photos

9.8
Excellent
38 Reviews

Northside Famlynest Lincoln Sq 4Br 2Ba 2P Rare Find

📍 2713 West Balmoral Avenue

From 270$

Check Availability

View all photos

9.7
Excellent
70 Reviews

Chicago Charm

📍 2139 West Granville Avenue

From 242$

Check Availability

View all photos

8.3
Very good
166 Reviews

Perfect Place To Enjoy The City Or Just Relax

📍 1902 South Sawyer Avenue

From 107$

Check Availability

View all photos

9.8
Excellent
30 Reviews

Wrigley Oasis! Steps From The Field! - 3Bd 1Ba

📍 1207 West Eddy Street

From 457$

Check Availability

View all photos

9.9
Excellent
21 Reviews

Serenity On The Shores

📍 6069 South Dune Harbor Drive

From 215$

Check Availability

Location