Chesterton Rentals
From $167 per night (USD)VRBO
Chesterton “Golf View Estate” Midwest Great Lake Beaches & Trails Of The Dunes!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Navigating the Coronavirus (COVID-19) In light of the coronavirus outbreak (COVID-19), We are ensuring cleanliness secon ...
From $167 per night (USD)VRBO
From $377 per night (USD)VRBO
Woodsy Retreat w/ River Near Dunes - ADA Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Adventure Awaits in this Woodsy Retreat 3 Bedrooms | 1.5 Bathrooms | Sleeps 6 Tucked beneath a canopy of trees and just ...
From $377 per night (USD)VRBO
From $375 per night (USD)VRBO
Spacious 4 BR 10 mins to 🏝 Near Chicago Sleeps 12
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 12
Don’t you want to go on Vacation but still feel the comfort of being home? Imagine being in a place 10 mins from the bea ...
From $375 per night (USD)VRBO
From $102 per night (USD)Expedia
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Downtown Chesterton private apartment. Walk to parks, dining, shopping, taverns, winery, European market, and more. On ...
From $102 per night (USD)Expedia
From $265 per night (USD)VRBO
Charming Chesterton Home: w/ Idyllic Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience historic Chesterton living from this spacious vacation rental - only a 5-minute walk to downtown! This 3-bedr ...
From $265 per night (USD)VRBO
From $282 per night (USD)Expedia
That 70’s Loft- Peace, Love and a Funky Stay!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Embrace the 70s vibe in our funky loft, where the inspiration is retro charm and modern comfort! Perfect for business ...
From $282 per night (USD)Expedia
From $287 per night (USD)VRBO
That 70’s Loft!- Peace, Love and A Funky Stay!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Embrace the 70s vibe in our funky loft, where the inspiration is retro charm and modern comfort! Perfect for business ...
From $287 per night (USD)VRBO
From $239 per night (USD)Expedia
Large Townhouse! Close to Dunes State Park: Short-Term Stays
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
+ Relax, recharge, and make memories at The Oasis—a spacious 1100 sq ft 2-bedroom townhome designed for comfort and conn ...
From $239 per night (USD)Expedia
From $222 per night (USD)VRBO
Chesterton Charmer: Upper Unit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a two-minute walk to downtown Chesterton! Guests will lov ...
From $222 per night (USD)VRBO
From $211 per night (USD)VRBO
Chesterton Charmer: Lower Unit
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Just a 15-minute drive from the Indiana Dunes/Lake Michigan, & a two-minute walk to downtown Chesterton! Guests will lov ...
From $211 per night (USD)VRBO
From $481 per night (USD)VRBO
Chesterton Charmer: 2 Units in 1
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
The perfect solution for 2 traveling families: Two separate units in the same house, conveniently located in the heart o ...
From $481 per night (USD)VRBO
From $218 per night (USD)VRBO
3-bedroom house in delightful Chesterton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in the desirable Chesterton area, just a short distance from downtown, this charming 4-bedroom, 2-bathroom home ...
From $218 per night (USD)VRBO
From $562 per night (USD)VRBO
Roomy Retreat–Family&Friends|2 King Beds|Game Room | Valpo University | Dunes
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to your perfect getaway in Chesterton, Indiana—an updated, pet-friendly rental home just minutes from the Indian ...
From $562 per night (USD)VRBO
From $319 per night (USD)Expedia
Cozy Abode ~ 3 Mi to Indiana Dunes Nat'l Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Leave your worries behind and head to this charming 4-bedroom, 2-bathroom vacation rental home in Chesterton for a rejuv ...
From $319 per night (USD)Expedia
From $165 per night (USD)VRBO
Cozy Modern Townhome in Unbeatable Chesterton Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Imagine living in a beautifully finished modern space just a stone's throw from the beach, vibrant downtown, and breatht ...
From $165 per night (USD)VRBO
From $367 per night (USD)Expedia
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
You will be arriving at a historically Pet Friendly rental home in Chesterton that gives way to chic and updated interio ...
From $367 per night (USD)Expedia
From $304 per night (USD)VRBO
INDIANA DUNES/LAKE MICHIGAN/DOWNTOWN CHESTERTON
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private house situated on a corner lot in bucolic downtown Chesterton, Indiana. With all the feels that a small town ha ...
From $304 per night (USD)VRBO
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Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stunning double-story Townhouse with prime location! 2 min from Downtown, walking distance from Dogwood Park, and 9 mi ...
Click For PricingExpedia
From $274 per night (USD)VRBO
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Stunning double- story Townhouse with prime location! 2 min from Downtown, walking distance from Dogwood park and 9 ...
From $274 per night (USD)VRBO
From $698 per night (USD)Expedia
Indiana Dunes Getaway on 2 acres! Truly unique 4 Bedroom, 4 Bath home!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this truly unique and beautiful 4 bedroom, 4 bath home located less than 10 minutes from the Indiana Dunes, an ...
From $698 per night (USD)Expedia
From $523 per night (USD)VRBO
Heart of Indiana Dunes National Park with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Message me for Off-season packages! On 3 wooded acres, our spacious home blends retro charm & modern amenities near Indi ...
From $523 per night (USD)VRBO
From $214 per night (USD)VRBO
Cozy home for a family to enjoy - only 7 miles away from Indiana Dunes park.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
An opportunity too good to pass up. This property features three bedrooms, including a queen-sized bed with a walk-in cl ...
From $214 per night (USD)VRBO
From $1149 per night (USD)VRBO
The Good Farm: Farmhouse + BarnBnB on 44 acres!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 17
Two separate dwellings on the same property. The farmhouse (sleeps 11) and BarnBnB (sleeps 6) is located on 44 acres of ...
From $1149 per night (USD)VRBO
From $444 per night (USD)Expedia
After-Dune Delight! Home with Pool and Fun for All
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Escape to your own private oasis in picturesque Porter, IN. This stunning vacation rental promises a perfect bl ...
From $444 per night (USD)Expedia
From $253 per night (USD)VRBO
A cozy home between the Indiana Dunes and town of Chesterton.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this ...
From $253 per night (USD)VRBO
From $273 per night (USD)Expedia
Dunes Homestead - Near Dunes + Lake + Dog Friendly\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to "The Dunes Homestead". Where all pets are welcome! Right in-between The Dunes National Park and downtown Ches ...
From $273 per night (USD)Expedia
From $309 per night (USD)VRBO
Blue Birdhouse - No Cleaning Fee - Pet Friendly - Dunes National Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the birdhouse, nestled near the Indiana Dunes National Lakeshore. Our charming 2-bed, 1-bath home is perfect ...
From $309 per night (USD)VRBO
From $158 per night (USD)VRBO
Cozy Cottage Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Be our guest in this cozy little rear cottage. 1 bedroom (Queen bed), Extra Queen size blow up mattress, 1 bath and full ...
From $158 per night (USD)VRBO
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Brand New Dunes Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the e ...
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From $665 per night (USD)VRBO
The Good Farm: 1853 Farmhouse on 44 acres
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Enjoy stunning views and disconnect from the hustle and bustle! The Good Farm (TGF) of Valpo allows you the peacefulness ...
From $665 per night (USD)VRBO
From $271 per night (USD)VRBO
The Good Farm: Barn BnB on 44 acres near Lake Mich
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy 44 acres just 15 minutes from the beaches of Lake Michigan! With room to sleep 6, guests will enjoy this fully sto ...
From $271 per night (USD)VRBO
From $204 per night (USD)Expedia
The \"Pool Barn Camper\" w/Hot Tub near Indiana Dunes
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fully equipped RV is parked in the driveway of our Pool Barn. RV sleeps 5, has bath with shower, stove, microwave, heat ...
From $204 per night (USD)Expedia
From $281 per night (USD)VRBO
The \"Pool Barn\" w/Pool, Hot Tub, Billiards & more near Indiana Dunes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 10
More than a place to sleep! Only 5 minutes to beaches of Indiana Dunes on Lake Michigan. Dunes National Park & hiking al ...
From $281 per night (USD)VRBO
From $1798 per night (USD)Expedia
2 miles from Dunes National Park. A Unique Boutique Hotel.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 20
You’ll be charmed by this adorable place to stay. This unique boutique hotel with lots of history. There is 5 rooms tota ...
From $1798 per night (USD)Expedia
From $338 per night (USD)VRBO
Summer/holiday fun Historic 40 A Farm Llama encounters chef service, near Lake M
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Moon-Shine on Coffee Creek - Historic farmhouse on 40 acre working farm. Cozy, quaint, more than century & half transiti ...
From $338 per night (USD)VRBO
From $495 per night (USD)Expedia
\"The Nook\"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Only two miles from the Indiana Dunes National Park and State Park, "The Nook" of the Indiana Dunes is your family's spe ...
From $495 per night (USD)Expedia
From $249 per night (USD)VRBO
The Waverly Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located an easy 1.6 miles to Indiana Dunes State Park, 2 miles South of Porter Beach, not even a mile from the South Sho ...
From $249 per night (USD)VRBO