Vacation Rentals Guide

Vacation Rentals in Chesterton

The Official Guide to Vacation Rentals in Chesterton – Your Trusted Source for the Best Stays!

Select dates
Guests
2 guests

Adults:

2

Children:

0

Child’s age:

Luxury Vacation Rentals Chesterton

View all photos

9.3
Excellent
35 Reviews

From

139$/night

Blue Birdhouse - Indiana Dunes - Pet Friendly

5 West Beam Street
Check Availability

View all photos

9.7
Excellent
9 Reviews

From

228$/night

Your Midwest Dunes Vacation Tri-State Paradise!

1541 Eagle Street
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

Cheap Vacation Rentals in Chesterton Indiana

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

Pet Friendly Vacation Rentals Chesterton Indiana

View all photos

8.1
Very good
27 Reviews

From

148$/night

Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms

105 West Michigan Avenue
Check Availability

View all photos

8.3
Very good
7 Reviews

From

472$/night

Roomy Retreat-Family & Friends 2 King Bed Game Room

130 Washington Avenue
Check Availability

View all photos

9.7
Excellent
149 Reviews

From

53$/night

Pulaski Point Properties

3936 North Pulaski Road
Check Availability

Chesterton Vacation Rentals Oceanfront

View all photos

9
Excellent
352 Reviews

From

82$/night

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

3558 North Wilton Avenue
Check Availability

View all photos

8.2
Very good
512 Reviews

From

51$/night

5430 Happy Home

5430 South Dearborn Street
Check Availability

View all photos

9.3
Excellent
227 Reviews

From

215$/night

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

1506 West Polk Street 3F
Check Availability

Chesterton Vacation Rentals with Private Pool

View all photos

9.7
Excellent
59 Reviews

From

124$/night

Irving Park Updated Vintage Top Unit 2-Flat

4036 North Saint Louis Avenue
Check Availability

View all photos

9.6
Excellent
129 Reviews

From

240$/night

The Avondale Guesthouse

2973 North Elston Avenue
Check Availability

View all photos

9.5
Excellent
101 Reviews

From

200$/night

1F Cozy Home In Little Italy Near Downtown West Loop United Center

1506 West Polk Street
Check Availability

View all photos

9.2
Excellent
144 Reviews

From

234$/night

Lincoln Park 3 Bedroom Penthouse

2633 North Sheffield Avenue
Check Availability

View all photos

9.3
Excellent
55 Reviews

From

123$/night

Fulbrix Bright Designer Apartments With West Loop Views

160 North Elizabeth Street
Check Availability

View all photos

9.8
Excellent
38 Reviews

From

270$/night

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

2713 West Balmoral Avenue
Check Availability

Location

Chesterton, Indiana, United States, 46304

Contact Us

YOUR DETAILS
SUBJECT
MESSAGE