Top 50 Chesterton Vacation Rentals

Houses (242)
Cottages (52)
Apartments (11)
Golf rental (238)
Ski rental (80)
Lake view (80)

Explore a selection of Chesterton vacation rentals

Beachwalk, 6 Bedrooms , Plus Den Sleeps 17 December 15-17, 201...
Guests17
Bedrooms6
Bathrooms5
Wonderful 4.9 / 5
$400 avg/night
6 beds
5 Bathrooms
Guests 17
53 reviews
Birchwood Cabin - Retreat Relax Revive-10 Minute Walk to Beach
Guests2
Bedroom1
Bathroom1
Wonderful 5 / 5
$115 avg/night
1 bed
1 Bathroom
Guests 2
52 reviews
Lake Front 4 bedroom Pine Lake w/pier 15 minute to Lake...
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.6 / 5
$210 avg/night
4 beds
3 Bathrooms
Guests 12
25 reviews
Beautiful Cottage Indiana Dunes Sheridan Beach Michigan City
Guests7
Bedrooms3
Bathroom1
Wonderful 4.4 / 5
$93 avg/night
3 beds
1 Bathroom
Guests 7
42 reviews
Steps Away From Sandy Beach Of Lake Michigan
Guests3
Bedroom1
Bathroom1
Wonderful 4.4 / 5
$88 avg/night
1 bed
1 Bathroom
Guests 3
22 reviews
Chicagoland NWI 4B/2B Home
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.6 / 5
$146 avg/night
4 beds
2 Bathrooms
Guests 8
12 reviews
Beach Home in Michigan City Resort Community-Steps from Beach and...
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.4 / 5
$265 avg/night
4 beds
2 Bathrooms
Guests 10
34 reviews
BEACH RENTAL! Sleeps 4!
Guests4
Bedroom1
Bathroom1
Wonderful 4.4 / 5
$150 avg/night
1 bed
1 Bathroom
Guests 4
36 reviews
Beautiful Lake Michigan Beach House Near Beach only 1 hr 15 mins...
Guests16
Bedrooms7
Bathrooms4
Wonderful 4.9 / 5
$799 avg/night
7 beds
4 Bathrooms
Guests 16
8 reviews
Charming Summer Cottage
Guests4
Bedrooms2
Bathroom1
Wonderful 4.5 / 5
$164 avg/night
2 beds
1 Bathroom
Guests 4
31 reviews
Perfect Long Beach Retreat to Gather with Your Family and Friends...
Guests13
Bedrooms4
Bathrooms4
Wonderful 4.4 / 5
$354 avg/night
4 beds
4 Bathrooms
Guests 13
13 reviews
Beach cottage with panoramic lake views and two fireplaces
Guests10
Bedrooms2
Bathrooms3
Wonderful 4.9 / 5
$300 avg/night
2 beds
3 Bathrooms
Guests 10
74 reviews
Artistic Loft close to Lake Michigan beaches, craft breweries...
Guests4
Bedroom1
Bathroom1
Wonderful 5 / 5
$119 avg/night
1 bed
1 Bathroom
Guests 4
17 reviews
Beautiful new home! Plenty of space indoor and outside. 5 bd/3.5...
Guests12
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$350 avg/night
5 beds
3 Bathrooms
Guests 12
21 reviews
LAKE VIEWS: Walk to Beach - Private Beach Access - Pet Friendly...
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$253 avg/night
2 beds
2 Bathrooms
Guests 4
3 reviews
Stunning Beachwalk Home, Sleeps 16
Guests16
Bedrooms5
Bathrooms3
Wonderful 4.7 / 5
$483 avg/night
5 beds
3 Bathrooms
Guests 16
7 reviews
Ideal for family reunions or large groups - Beach House sleeps 24
Guests24
Bedrooms8
Bathrooms6
Wonderful 4.5 / 5
$750 avg/night
8 beds
6 Bathrooms
Guests 24
14 reviews
Enjoy fall colors and hiking -- Family/Pet Friendly, By Beach...
Guests6
Bedrooms3
Bathroom1
Wonderful 4.7 / 5
$92 avg/night
3 beds
1 Bathroom
Guests 6
16 reviews
Quiet and woodsy 2 bedroom 2 bath, 8 min walk to beach
Guests8
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$130 avg/night
2 beds
2 Bathrooms
Guests 8
16 reviews
Gorgeous place "NaSeli" for vacation,b-day party or just relax.5...
Guests20
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$450 avg/night
5 beds
3 Bathrooms
Guests 20
33 reviews
Lovely Cottage in Beachwalk Resort sleeps 6! Reserve Summer Vaykay...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.6 / 5
$180 avg/night
2 beds
2 Bathrooms
Guests 6
9 reviews
Steps From Lake Michican - Family Friendly - 3 Bedroom Spacious...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$154 avg/night
3 beds
2 Bathrooms
Guests 8
8 reviews
Celebration House Sleeps 12 4 Bedroom 2 1/2 Bath Private Beach...
Guests12
Bedrooms4
Bathrooms2
Wonderful 4.7 / 5
$612 avg/night
4 beds
2 Bathrooms
Guests 12
20 reviews
The garden, grill and get away......from almost everything.
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.3 / 5
$206 avg/night
3 beds
2 Bathrooms
Guests 8
12 reviews
SHELSKY: Walk to Beach - Grand Beach - Spacious - Big Families...
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.5 / 5
$315 avg/night
3 beds
2 Bathrooms
Guests 10
2 reviews
Beachwalk Resort 2/2 w/ Golf Cart
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$189 avg/night
2 beds
1 Bathroom
Guests 4
11 reviews
Norse Heaven in the Beachwalk
Guests10
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$250 avg/night
4 beds
4 Bathrooms
Guests 10
3 reviews
Beach, bikes and family fun. 60 miles from Chicago and steps from...
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$250 avg/night
4 beds
3 Bathrooms
Guests 8
31 reviews
Beachfront/Hot Tub(all year)Steam Room/Jacuzzi/Pets/2Night...
Guests4
Bedroom1
Bathrooms2
Wonderful 4.8 / 5
$225 avg/night
1 bed
2 Bathrooms
Guests 4
78 reviews
FREE Ice/Soda/More -- Most Hi Tech -- Theater, Hot Tub, xBox, TVs...
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$418 avg/night
4 beds
3 Bathrooms
Guests 12
40 reviews
Cozy Country Cottage PineLake 'Home Away from Home'
Guests6
Bedrooms2
Bathrooms0
Wonderful 5 / 5
$135 avg/night
2 beds
0 Bathrooms
Guests 6
25 reviews
Discount Fall/Winter. Moments to the POOL & Lake Kai. ONLY 1 block...
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.4 / 5
$400 avg/night
4 beds
3 Bathrooms
Guests 12
17 reviews
Charming Cottage A Few Short Steps To The Beach with heated pool!!
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$457 avg/night
2 beds
2 Bathrooms
Guests 6
5 reviews
Relaxing modern home with lake views from every room
Guests14
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$640 avg/night
5 beds
4 Bathrooms
Guests 14
89 reviews
Beautiful 4 Bed, 3 1/2 Bath with private putting green!
Guests12
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$343 avg/night
4 beds
3 Bathrooms
Guests 12
16 reviews
Michiana Shores 2BR 2BA Charming Home - Short Walk to the Beach!
Guests8
Bedrooms2
Bathrooms2
Wonderful 4.4 / 5
$210 avg/night
2 beds
2 Bathrooms
Guests 8
10 reviews
Modern Hideaway for Two Yet Close to the Lake!
Guests2
Bedroom1
Bathrooms0
Wonderful 4.8 / 5
$175 avg/night
1 bed
0 Bathrooms
Guests 2
37 reviews
View of the lake from 2 decks in this 6BR Lake Shore Dr home...
Guests18
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$400 avg/night
5 beds
3 Bathrooms
Guests 18
16 reviews
Vacation Rental on Beachwalk Lane, Sleeps 11, Only Steps from Beach
Guests11
Bedrooms4
Bathrooms3
Wonderful 4.6 / 5
$466 avg/night
4 beds
3 Bathrooms
Guests 11
19 reviews
Beautiful house located on Beachwalk Lane, sleeps 11, steps to the...
Guests11
Bedrooms4
Bathrooms3
Wonderful 4.6 / 5
$466 avg/night
4 beds
3 Bathrooms
Guests 11
19 reviews
Beach home - Perfect Getaway
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.8 / 5
$205 avg/night
4 beds
2 Bathrooms
Guests 10
10 reviews
Perfect location for Notre Dame games, wine festivals, shopping...
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$250 avg/night
3 beds
2 Bathrooms
Guests 10
23 reviews
Adorable Cottage New Buffalo. Near Grand Beach
Guests5
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$133 avg/night
1 bed
1 Bathroom
Guests 5
50 reviews
Beautiful new construction 4-5 bed, 4.5+ bath, Grand Beach, htd...
Guests15
Bedrooms4
Bathrooms5
Wonderful 5 / 5
$500 avg/night
4 beds
5 Bathrooms
Guests 15
7 reviews
Summer Option, Great Family Home, 5bedrooms, 3.5 baths
Guests12
Bedrooms5
Bathrooms2
Wonderful 4.8 / 5
$400 avg/night
5 beds
2 Bathrooms
Guests 12
5 reviews
Dreamwold House- Retreat Relax Revive- 10 Minute Walk to Beach
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$175 avg/night
3 beds
2 Bathrooms
Guests 6
60 reviews
Savannah has Off Street Parking and is a Short Walk to the Beach
Guests10
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$387 avg/night
3 beds
3 Bathrooms
Guests 10
30 reviews
✅ GREAT FALL WEEKDAY STAYS - 2 DAY MIN - $ 90 DAYS
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$90 avg/night
2 beds
1 Bathroom
Guests 5
21 reviews
Steps Away from the Sandy Beach by Michigan Lake! Wi-Fi Hdtv
Guests2
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$85 avg/night
1 bed
1 Bathroom
Guests 2
26 reviews
Lake Michigan Getaway
Guests8
Bedrooms3
Bathroom1
Wonderful 4.2 / 5
$143 avg/night
3 beds
1 Bathroom
Guests 8
22 reviews

Chesterton, IN, USA Vacation Rentals

Beachwalk, 6 Bedrooms , Plus Den Sleeps 17 December 15-17, 201...

Birchwood Cabin - Retreat Relax Revive-10 Minute Walk to Beach

Lake Front 4 bedroom Pine Lake w/pier 15 minute to Lake...

Beautiful Cottage Indiana Dunes Sheridan Beach Michigan City

Steps Away From Sandy Beach Of Lake Michigan

Chicagoland NWI 4B/2B Home

Beach Home in Michigan City Resort Community-Steps from Beach and...

BEACH RENTAL! Sleeps 4!

Beautiful Lake Michigan Beach House Near Beach only 1 hr 15 mins...

Charming Summer Cottage

Perfect Long Beach Retreat to Gather with Your Family and Friends...

Beach cottage with panoramic lake views and two fireplaces

Artistic Loft close to Lake Michigan beaches, craft breweries...

Beautiful new home! Plenty of space indoor and outside. 5 bd/3.5...

LAKE VIEWS: Walk to Beach - Private Beach Access - Pet Friendly...

Stunning Beachwalk Home, Sleeps 16

Ideal for family reunions or large groups - Beach House sleeps 24

Enjoy fall colors and hiking -- Family/Pet Friendly, By Beach...

Quiet and woodsy 2 bedroom 2 bath, 8 min walk to beach

Gorgeous place "NaSeli" for vacation,b-day party or just relax.5...

Lovely Cottage in Beachwalk Resort sleeps 6! Reserve Summer Vaykay...

Steps From Lake Michican - Family Friendly - 3 Bedroom Spacious...

Celebration House Sleeps 12 4 Bedroom 2 1/2 Bath Private Beach...

The garden, grill and get away......from almost everything.

SHELSKY: Walk to Beach - Grand Beach - Spacious - Big Families...

Beachwalk Resort 2/2 w/ Golf Cart

Norse Heaven in the Beachwalk

Beach, bikes and family fun. 60 miles from Chicago and steps from...

Beachfront/Hot Tub(all year)Steam Room/Jacuzzi/Pets/2Night...

FREE Ice/Soda/More -- Most Hi Tech -- Theater, Hot Tub, xBox, TVs...

Cozy Country Cottage PineLake 'Home Away from Home'

Discount Fall/Winter. Moments to the POOL & Lake Kai. ONLY 1 block...

Charming Cottage A Few Short Steps To The Beach with heated pool!!

Relaxing modern home with lake views from every room

Beautiful 4 Bed, 3 1/2 Bath with private putting green!

Michiana Shores 2BR 2BA Charming Home - Short Walk to the Beach!

Modern Hideaway for Two Yet Close to the Lake!

View of the lake from 2 decks in this 6BR Lake Shore Dr home...

Vacation Rental on Beachwalk Lane, Sleeps 11, Only Steps from Beach

Beautiful house located on Beachwalk Lane, sleeps 11, steps to the...

Beach home - Perfect Getaway

Perfect location for Notre Dame games, wine festivals, shopping...

Adorable Cottage New Buffalo. Near Grand Beach

Beautiful new construction 4-5 bed, 4.5+ bath, Grand Beach, htd...

Summer Option, Great Family Home, 5bedrooms, 3.5 baths

Dreamwold House- Retreat Relax Revive- 10 Minute Walk to Beach

Savannah has Off Street Parking and is a Short Walk to the Beach

✅ GREAT FALL WEEKDAY STAYS - 2 DAY MIN - $ 90 DAYS

Steps Away from the Sandy Beach by Michigan Lake! Wi-Fi Hdtv

Lake Michigan Getaway