We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Chesterton

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 km
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
50 rentals in Chesterton.
Sort by:
Tripadvisor Sort
Chesterton “Golf View Estate” Midwest  Great Lake Beaches & Trails Of The Dunes!, holiday rental in Chesterton

Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool, holiday rental in Chesterton

5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool

5 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
NEW! Quaint Chesterton Home in Walkable Location!, holiday rental in Chesterton

NEW! Quaint Chesterton Home in Walkable Location!

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Classic Roomy Cottage.  Best walk-to-everything location., holiday rental in Chesterton

Classic Roomy Cottage. Best walk-to-everything location.

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Spacious, Fun and Family Friendly Beach Home, holiday rental in Chesterton

Spacious, Fun and Family Friendly Beach Home

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping, holiday rental in Chesterton

Artistic Loft close to Lake Michigan beaches, craft breweries & outlet shopping

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Dune Fine Is A Brand New Family Friendly Home Right On The Beach, holiday rental in Chesterton

Dune Fine Is A Brand New Family Friendly Home Right On The Beach

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Beautiful New Home!   Book Now, Summer is filling up fast!!, holiday rental in Chesterton

Beautiful New Home! Book Now, Summer is filling up fast!!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Family Home Near Downtown Valpo & University, holiday rental in Chesterton

Family Home Near Downtown Valpo & University

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Indiana Dunes Beach Rental, holiday rental in Chesterton

Indiana Dunes Beach Rental

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Save time - get the best Chesterton rentals sent straight to your email!
Beautiful Beach Cottage - 205 California Ave, holiday rental in Chesterton

Beautiful Beach Cottage - 205 California Ave

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
'How You Dune?'- Lake Michigan Beach House Perfect For Large Groups!, holiday rental in Chesterton

'How You Dune?'- Lake Michigan Beach House Perfect For Large Groups!

7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled, holiday rental in Chesterton

Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Rare Private Pool w/in 1.5 Blocks to the Beach!, holiday rental in Chesterton

Rare Private Pool w/in 1.5 Blocks to the Beach!

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Cozy and Charming Beach Getaway on Lovely Lake Michigan, holiday rental in Chesterton

Cozy and Charming Beach Getaway on Lovely Lake Michigan

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Charming Beach Front Cottages, holiday rental in Chesterton

Charming Beach Front Cottages

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo, holiday rental in Chesterton

New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Beautiful  apt next to Lighthouse Outlet Mall, holiday rental in Chesterton

Beautiful apt next to Lighthouse Outlet Mall

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17, holiday rental in Chesterton

Vintage Lake Michigan Beach Cottage: 4br+loft,3ba-Sleeps 17

4 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Vintage Cottage with Covid Protocols, holiday rental in Chesterton

Vintage Cottage with Covid Protocols

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Casa Blanca in Miller Beach, holiday rental in Chesterton

Casa Blanca in Miller Beach

6 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo, holiday rental in Chesterton

New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!, holiday rental in Chesterton

Lighthouse apt. Great location right by Lighthouse Outlet Mall See the Sale!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Walk to Lake Michigan Beach! Sleeps 12 - 14!, holiday rental in Chesterton

Walk to Lake Michigan Beach! Sleeps 12 - 14!

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Two-Bedroom Apartment by Lighthouse Outlet Mall, holiday rental in Chesterton

Two-Bedroom Apartment by Lighthouse Outlet Mall

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lovely Lake Michigan Beach Rental, holiday rental in Chesterton

Lovely Lake Michigan Beach Rental

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Big Cozy House In The Dunes (5bed/3.5bath plus loft) - Nested In Wooded Hillside, holiday rental in Chesterton

Big Cozy House In The Dunes (5bed/3.5bath plus loft) - Nested In Wooded Hillside

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to  Notre Dame, holiday rental in Chesterton

Stunning Home (Sleeps 16) Hot Tub, Firepit, Large Yard -45 min to Notre Dame

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Nice   beach   house, holiday rental in Chesterton

Nice beach house

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Studio apt. across from Lighthouse Outlet Mall, holiday rental in Chesterton

Studio apt. across from Lighthouse Outlet Mall

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lake House on beach path, sleeps 12!, holiday rental in Chesterton

Lake House on beach path, sleeps 12!

2 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
5BD 2BA Cottage walking distance to Sheridan Beach & 30 min drive to Norte Dame, holiday rental in Chesterton

5BD 2BA Cottage walking distance to Sheridan Beach & 30 min drive to Norte Dame

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes, holiday rental in Chesterton

Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Brand New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo, holiday rental in Chesterton

Brand New Rehab! Beautiful Beach Rental Close To Beach, Park, & Zoo

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
A great time for a weekend get away!!!, holiday rental in Chesterton

A great time for a weekend get away!!!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Minutes to beach, businesses and train!, holiday rental in Chesterton

Minutes to beach, businesses and train!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
CONDO FOR RENT IN FLORIDA, holiday rental in Chesterton

CONDO FOR RENT IN FLORIDA

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lake Michigan Sheridan Beach w/private off street parking + Billiard Table, holiday rental in Chesterton

Lake Michigan Sheridan Beach w/private off street parking + Billiard Table

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
DunesWalk Inn - Vacation Rental, holiday rental in Chesterton

DunesWalk Inn - Vacation Rental

5 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Dune our Thing- 1 block to beach with private parking and lake views!, holiday rental in Chesterton

Dune our Thing- 1 block to beach with private parking and lake views!

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
ON THE BEACH, holiday rental in Chesterton

ON THE BEACH

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Beach Cottage* Walk 800 ft. to Lake Michigan's Sheridan Beach* NEW LISTING, holiday rental in Chesterton

Beach Cottage* Walk 800 ft. to Lake Michigan's Sheridan Beach* NEW LISTING

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
NEW LISTING! Lake Michigan Views | Multi-Level  | Sleeps 6 | 2 Car Garage, holiday rental in Chesterton

NEW LISTING! Lake Michigan Views | Multi-Level | Sleeps 6 | 2 Car Garage

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
Miller Beach and Indiana Dunes National Park Vacation House, holiday rental in Chesterton

Miller Beach and Indiana Dunes National Park Vacation House

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Bookabach.co.nz logo
Check-in
Check-out
NEW! Stylish Home w/ Elevated Deck, Walk to Beach!, holiday rental in Chesterton

NEW! Stylish Home w/ Elevated Deck, Walk to Beach!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Lakefront Family Retreat w/ Grill: Steps to Beach!, holiday rental in Chesterton

Lakefront Family Retreat w/ Grill: Steps to Beach!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sunflower Cottage by the beach, parks, zoo and more., holiday rental in Chesterton

Sunflower Cottage by the beach, parks, zoo and more.

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
NEW! Well-Appointed Gary Home Few Blocks to Beach!, holiday rental in Chesterton

NEW! Well-Appointed Gary Home Few Blocks to Beach!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Creature Comforts at Catalpa, holiday rental in Chesterton

Creature Comforts at Catalpa

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
It's the Wright Farm, holiday rental in Chesterton

It's the Wright Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Chesterton