Photo by Susan Ross

Search Chesterton Villa Rentals from CA $383

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Chesterton villas

A secluded cabin area with multiple wooden cabins surrounded by dense forest.

1. Wild Indigo - Upscale 2 Bedroom Villa at Petite Acres

Wild Indigo - Upscale 2 Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $467
CA $749 total
includes taxes & fees
Nov 17 - Nov 18
Wild Indigo - Upscale 2 Bedroom Villa at Petite Acres
A modern wooden cabin with large windows, surrounded by trees.

2. Windflower - Upscale 2 Bedroom Villa at Petite Acres

Windflower - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Windflower - Upscale 2 Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

3. Woodsage - Upscale 2 Bedroom Villa at Petite Acres

Woodsage - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Woodsage - Upscale 2 Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

4. Wolfsbane - Upscale 2 Bedroom Villa at Petite Acres

Wolfsbane - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Wolfsbane - Upscale 2 Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

5. Larkspur - Upscale 2 Bedroom Villa at Petite Acres

Larkspur - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Larkspur - Upscale 2 Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

6. Dogwood - Upscale 2 Bedroom Villa at Petite Acres

Dogwood - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Dogwood - Upscale 2 Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

7. Bellflower - Cozy One Bedroom Villa at Petite Acres

Bellflower - Cozy One Bedroom Villa at Petite Acres
New Buffalo
The price is CA $391
CA $648 total
includes taxes & fees
Nov 10 - Nov 11
Bellflower - Cozy One Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

8. Pied-à-terre Allium - The Bunk House at Petite Acres

Pied-à-terre Allium - The Bunk House at Petite Acres
New Buffalo
10.0 out of 10, Exceptional, (1 review)
"Very cute, great for a girls trip"
United States
Lauren A.
The price is CA $574
CA $1,139 total
includes taxes & fees
Nov 10 - Nov 11
Pied-à-terre Allium - The Bunk House at Petite Acres
A modern house with a large glass front, surrounded by trees.

9. Coral Bells - Cozy One Bedroom Villa at Petite Acres

Coral Bells - Cozy One Bedroom Villa at Petite Acres
New Buffalo
The price is CA $391
CA $648 total
includes taxes & fees
Nov 10 - Nov 11
Coral Bells - Cozy One Bedroom Villa at Petite Acres
A cabin with a sloped roof surrounded by a forest.

10. Goldenrod -Upscale 2 Bedroom at Petite Acres

Goldenrod -Upscale 2 Bedroom at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Goldenrod -Upscale 2 Bedroom at Petite Acres
A secluded cabin area with multiple wooden cabins surrounded by dense forest.

11. Wolfsbane - Upscale 2 Bedroom Villa at Petite Acres

Wolfsbane - Upscale 2 Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $438
CA $718 total
includes taxes & fees
Nov 15 - Nov 16
Wolfsbane - Upscale 2 Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

12. Wild Indigo - Upscale 2 Bedroom Villa at Petite Acres

Wild Indigo - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Wild Indigo - Upscale 2 Bedroom Villa at Petite Acres
A modern house with a large glass front, surrounded by trees.

13. Witch Hazel - Upscale 2 Bedroom Villa at Petite Acres

Witch Hazel - Upscale 2 Bedroom Villa at Petite Acres
New Buffalo
The price is CA $421
CA $755 total
includes taxes & fees
Nov 10 - Nov 11
Witch Hazel - Upscale 2 Bedroom Villa at Petite Acres
A row of cabins surrounded by trees, with a clear sky above.

14. Larkspur - Upscale 2 Bedroom Villa at Petite Acres

Larkspur - Upscale 2 Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $428
CA $708 total
includes taxes & fees
Nov 23 - Nov 24
Larkspur - Upscale 2 Bedroom Villa at Petite Acres
A row of cabins surrounded by trees, with a clear sky above.

15. Coral Bells - Cozy One Bedroom Villa at Petite Acres

Coral Bells - Cozy One Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $384
CA $599 total
includes taxes & fees
Nov 15 - Nov 16
Coral Bells - Cozy One Bedroom Villa at Petite Acres
Two people roasting marshmallows over a fire pit outdoors.

16. Witch Hazel - Upscale 2 Bedroom Villa at Petite Acres

Witch Hazel - Upscale 2 Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $428
CA $708 total
includes taxes & fees
Nov 23 - Nov 24
Witch Hazel - Upscale 2 Bedroom Villa at Petite Acres
A secluded cabin area with multiple wooden cabins surrounded by dense forest.

17. Woodsage - Upscale 2 Bedroom Villa at Petite Acres

Woodsage - Upscale 2 Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $414
CA $693 total
includes taxes & fees
Nov 15 - Nov 16
Woodsage - Upscale 2 Bedroom Villa at Petite Acres
A row of cabins surrounded by trees, with a clear sky above.

18. Dogwood - Upscale 2 Bedroom Villa at Petite Acres

Dogwood - Upscale 2 Bedroom Villa at Petite Acres
3.0 star property
New Buffalo
The price is CA $458
CA $739 total
includes taxes & fees
Nov 15 - Nov 16
Dogwood - Upscale 2 Bedroom Villa at Petite Acres
A residential area with multiple houses, a covered outdoor seating area, and a well-maintained lawn.

19. Pied-à-terre Allium - The Bunk House at Petite Acres

Pied-à-terre Allium - The Bunk House at Petite Acres
3.5 star property
New Buffalo
The price is CA $617
CA $1,096 total
includes taxes & fees
Nov 18 - Nov 19
Pied-à-terre Allium - The Bunk House at Petite Acres
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Learn more about Chesterton

Nestled along Lake Michigan's shore, this small town offers scenic trails through Indiana Dunes National Park for hiking and birdwatching. Coffee shops and local restaurants line the historic downtown, while nearby beaches provide perfect spots for summer swimming and sunset views.

See all hotels in Chesterton
A wooden staircase leading up a sandy hill with dense green forest in the background.
Photo by Susan Ross
Open Photo by Susan Ross

Top reviews in Chesterton

A hotel with a modern design, featuring a mix of white and orange buildings, a parking lot, and a flagpole with an American flag.
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton
Chesterton

10/10 Excellent

Clean rooms. Helpful staff. Food at the bar was very good.
Canada
Scott
Reviewed July 26, 2026
Hilton Garden Inn Chesterton

Frequently Asked Questions

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What is there to do near my villa in Chesterton?

Whatever you love doing, Chesterton has loads to keep you on the hop. Indiana Dunes State Park, Dune Acres Beach and Coffee Creek Watershed Conservancy Preserve are on most travelers' schedules. Don't forget about Lustron House, Chellberg Farm and Cowles Bog Trailhead either. With Expedia's Chesterton hotel deals, you'll be able to discover even more fabulous attractions like these with the money you save.

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