Holiday rentals in Chesterton
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chesterton
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton holiday rentals
Other great holiday rentals in Chesterton
Guest favourite
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
20–27 Dec
£132 per night
Superhost
Home in Chesterton
4.88 out of 5 average rating, 41 reviewsDunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home
24–31 Jan
£136 per night
Guest favourite
Home in Chesterton
4.95 out of 5 average rating, 39 reviewsBlue Birdhouse by the Beach - No Cleaning Fee
7–14 Nov
£159 per night
Guest favourite
Home in Valparaiso
4.97 out of 5 average rating, 88 reviewsCozy Luxe Downtown Valparaiso Stay
2–9 Jun
£126 per night
Guest favourite
Apartment in Portage
4.96 out of 5 average rating, 78 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
3–10 Mar
£128 per night
Guest favourite
Cottage in Valparaiso
4.96 out of 5 average rating, 49 reviewsCozy 2 Bedroom Valparaiso Cottage
16–23 Jul
£124 per night
Guest favourite
Tiny home in Michigan City
4.97 out of 5 average rating, 76 reviewsThe Studio at the Dunes
24 Feb – 3 Mar
£135 per night
Guest favourite
Home in Trail Creek
4.99 out of 5 average rating, 68 reviewsLeo Lodge
7–14 Feb
£104 per night
Quick stats about holiday rentals in Chesterton
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
£8 before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- West Lafayette Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Chicago Holiday rentals
- Rentals with a firepit Chesterton
- Monthly Rentals Chesterton
- Rentals with a patio Chesterton
- Pet-friendly rentals Chesterton
- House rentals Chesterton
- Family-friendly rentals Chesterton
- Family-friendly rentals Chesterton
- Rentals with outdoor seating Chesterton
- Cabin rentals Chesterton
- Rentals with a washing machine and dryer Chesterton
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom