Holiday Rentals in Chesterton
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50 rentals in Chesterton.
Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Kayak Launch and Zip Line LONG TERM OPTIONS AVAILABLE
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Chesterton Historical Downtown Indiana Dunes Beach National Park Dog Friendly
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Sweet Home in Chesterton
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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INDIANA DUNES/LAKE MICHIGAN/DOWNTOWN CHESTERTON
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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NEW! Cozy Abode ~ 3 Mi to Indiana Dunes Nat’l Park
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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DunesWalk Inn at the Furness Mansion - Indiana Dunes - Sleeps 1-19
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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11th Street Lodge-Downtown Chesterton
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Coffee Creek Retreat
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Beautiful Riverfront Home on 10 Acres!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Wooded retreat! An upper level studio with private entrance, pool and Hot Tub.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Lakefront Cottage in Indiana Dunes
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Porter Beach Vacation Getway! Lake Michigan Beachside Home - Newly Remodeled
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Indiana Dunes Beach Rental
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy and Charming Beach Getaway on Lovely Lake Michigan
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Beach Front Cottages
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovely Lake Michigan Beach Rental
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Views From Beachfront Unit In the Heart of the Indiana Dunes
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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"The Nook" 2mi- Dunes,Beach,Chesterton w/FirePit,Backyard,GameRoom,1pm☑️-IN/OUT
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Indiana Dunes Retreat - Beautiful Home Close To Lake Beach and National Park! 20
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern FarmHouse Stay On 12 Acres with Fireplace and Hot Tub, Sleeps 16
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Lake Michigan, Indiana Beachfront Vacation Rental
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Log Cabin Near Indiana Dunes & Lake Michigan!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Secluded Hideaway in the Dunes
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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DunesWalk Inn - Vacation Rental
Condo/Apartment
5 bedrooms
5 bathrooms
Sleeps 19
Match: Sleeps
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Urban living, close to malls, beach, in between Chicago and Michigan, quiet
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Lake Michigan Beach House
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Dune Retreat in Beverly Shores, Pole Barn Fire Pit and Hot Tub
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Comfort and Convenience! 2 Sleek Units, Free Parking, Pets Allowed
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Prime Location! 2 Comfortable Units, Free Parking, Close to Alton Goin Museum
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Just What You Were Looking For! 3 Comfortable Units, Pets Allowed
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Miles of Parks and Trails! Explore Portage Imagination Glen Park, Indiana Dunes
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Convenient Stay in Indiana! Free Parking, Close to Portage Riverwalk
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Affordability Meets Comfort! Pets Allowed, Free Parking Onsite
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Travel Destination! 2 Pet-Friendly Units, Free Parking, Close to West Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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You Found it! Three Pet-Friendly Units, Free Parking, Close to Diana Dunes Dare
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Budget-Friendly Comfort & Convenience, Minutes to Founders Square
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Best Place to Stay in Indiana! 4 Modern Units, Near Indiana Dunes, West Beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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4 Budget-Friendly Units, Free Parking Onsite, Minutes to Ogden Dunes
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Comfort & Convenience! Free Parking, Pet-Friendly, Minutes to Ogden Dunes
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pleasant Stay, Convenient Location! Near Diana Dunes Dare
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Prime Location, 4 Sleek Units w/Free Parking, Minutes to Lake Shel-oole
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Explore Indiana Dunes National Park! Four Comfortable Units, Free Parking
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Four Pet-Friendly Units, Free Parking Onsite, Near Alton Goin Museum
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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The "Pool Barn Camper" w/Hot Tub near Indiana Dunes
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The "Pool Barn" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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Spacious 4 BR 10 mins to Near Chicago Sleeps 12
Holiday Rental House
1 bedroom
0 bathrooms
Sleeps 12
Match: Sleeps
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The Lake Place
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Cottage Guest House
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Chesterton
- Yes, here are some popular holiday rentals in Chesterton that have a pool:
- 5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool
- Chesterton Historical Downtown Indiana Dunes Beach National Park Dog Friendly
- NEW! Cozy Abode ~ 3 Mi to Indiana Dunes Nat’l Park
- Yes, here are some popular holiday rentals in Chesterton that have internet access:
- 5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool
- Chesterton Historical Downtown Indiana Dunes Beach National Park Dog Friendly
- NEW! Cozy Abode ~ 3 Mi to Indiana Dunes Nat’l Park
- Some of the most popular kid friendly rentals in Chesterton are:
- 5 Bdrm 3 Bth Lake Michigan Waterfront Private Pool
- Chesterton Historical Downtown Indiana Dunes Beach National Park Dog Friendly
- NEW! Cozy Abode ~ 3 Mi to Indiana Dunes Nat’l Park