Vacation rentals in Chesterton
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Chesterton
Guests agree: these vacation rentals 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 vacation rentals
Other great vacation rentals in Chesterton
Home in De Motte
4.95 out of 5 average rating, 211 reviewsCountry Cottage
Guesthouse in Plymouth
4.99 out of 5 average rating, 494 reviewsSue's Place
Home in Portage
4.92 out of 5 average rating, 151 reviewsNewly Renovated with Finished Basement
Cabin in Michigan City
4.95 out of 5 average rating, 402 reviewsLittle Copper Cabin
Bungalow in Valparaiso
4.9 out of 5 average rating, 306 reviewsClose to VU and amazing downtown
Guesthouse in Valparaiso
4.96 out of 5 average rating, 161 reviewsPrivate Cottage in Gated Nudist Community
Home in Michigan City
4.94 out of 5 average rating, 404 reviewsSmall Clean Home Near Beach, Casino, Outlet Mall
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
Other great vacation rentals in Chesterton
Cottage in Valparaiso
4.96 out of 5 average rating, 50 reviewsCozy 2 Bedroom Valparaiso Cottage
Home in Porter
4.91 out of 5 average rating, 43 reviewsThe Dune Den! Huge Yard/Firepit/Near Town+Dunes
Home in Trail Creek
4.99 out of 5 average rating, 69 reviewsLeo Lodge
Apartment in Michigan City
5.0 out of 5 average rating, 20 reviewsBrick Bungalow Upper Unit: Beach, Casino, Wineries
Condo in Portage
5.0 out of 5 average rating, 54 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Condo in Portage
4.94 out of 5 average rating, 68 reviewsUnsalted Stay - Waterfront Condo
Apartment in Michigan City
5.0 out of 5 average rating, 53 reviewsFresh 1 bedroom apartment downtown Michigan City
Tiny home in Michigan City
4.98 out of 5 average rating, 80 reviewsThe Studio at the Dunes
Quick stats about vacation 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
$10 before taxes and fees
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Chesterton?
Yes! Work meets play with ease at over 30 vacation rentals in Chesterton featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesterton?
Four-legged friends are welcome in Chesterton. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Chesterton?
Experience the best of Chesterton with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesterton have wifi?
Absolutely! We offer over 30 house rentals with wifi in Chesterton. Enjoy a tailored experience with all the comforts you desire.
Destinations to explore
- Downtown Chicago Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- West Lafayette Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- Chicago Vacation rentals
- Family-friendly rentals Chesterton
- Cabin rentals Chesterton
- Rentals with a washer and dryer Chesterton
- Pet-friendly rentals Chesterton
- Rentals with a patio Chesterton
- House rentals Chesterton
- Rentals with outdoor seating Chesterton
- Kid-friendly rentals Chesterton
- Rentals with a fire pit Chesterton
- Monthly Rentals Chesterton
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes