
House vacation rentals in Chesterton
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterton
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton house rentals
House rentals with a pool

Notre Dame Haus: Pool, Game room & 5 min to campus

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Beautiful home with Beach views in Beachwalk

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Pool House near the Indiana Dunes

New Hot Tub Community pool Union Pier

Home near the lake with an inground pool

Entire House With Pool - Backyard Beach Getaway
Weekly house rentals

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

18 acres | Arcades | Heated Pool | Hot Tub | Pond

In-town Lovely Home! Steps to Starbucks & Beach!

Long-Term Spacious House for Rent

3BR w/sauna, tanning bed, hot tub 3.9 miles fromND

Sleeps 15, 7 bedrooms, 4 baths, 2 kitchens

CREW House on the lake #hottub #Parents&Kids love

Quaint 2 bed home newly renovated mid term rental
Private house rentals

Vip! 4BD 5 min to Lake, W pool heater.

Serenity House on the River

Renovated french country lake home. 6bedroom/4bath

Irish Retreat

Pure Michiana - Rustic & Cozy - near the stateline

5 Bedroom House "Quiet Street right off the Lake"

Serene Settings

Small Clean Home Near Beach, Casino, Outlet Mall
Quick stats about house rentals in Chesterton
Total rentals
40 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- University of Notre Dame
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Potato Creek State Park
- Flossmoor Golf Club
- Brookfield Zoo
- Garfield Park Conservatory
- Chicago Cultural Center
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