Best Chesterton Vacation Rentals
Blue Birdhouse - Indiana Dunes - Pet Friendly
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Situated 3.2 km from Cowles Bog Trail, the 2-bedroom Blue Birdhouse - Indiana Dunes - Pet Friendly Chesterton villa entices guests to explore various tourist attractions in the area. The holiday home hosts up to 6 guests and provides them with a private parking lot.
Blue Birdhouse - Indiana Dunes - Pet Friendly
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Blue Birdhouse - Indiana Dunes - Pet Friendly
Situated 3.2 km from Cowles Bog Trail, the 2-bedroom Blue Birdhouse - Indiana Dunes - Pet Friendly Chesterton villa entices guests to explore various tourist attractions in the area. The holiday home hosts up to 6 guests and provides them with a private parking lot.
Your Midwest Dunes Vacation Tri-State Paradise!
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Entertainment
- Sun terrace
To enjoy your vacation in Chesterton, stay at the spacious 139 m² Your Midwest Dunes Vacation Tri-State Paradise! Chesterton apartment, which is around a 10-minute drive from Chesterton Art Center and within 6 km of Splash Down Dunes Waterpark. The 2-bedroom apartment features Wi-Fi, along with a charging station for electric vehicles for guests travelling by car.
Entertainment and leisure options at the apartment include a nightclub and a casino, as well as a sundeck, a picnic area, and a golf course. Various sport options, such as darts, are provided in the area.
Your Midwest Dunes Vacation Tri-State Paradise!
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Entertainment
- Sun terrace
Your Midwest Dunes Vacation Tri-State Paradise!
To enjoy your vacation in Chesterton, stay at the spacious 139 m² Your Midwest Dunes Vacation Tri-State Paradise! Chesterton apartment, which is around a 10-minute drive from Chesterton Art Center and within 6 km of Splash Down Dunes Waterpark. The 2-bedroom apartment features Wi-Fi, along with a charging station for electric vehicles for guests travelling by car.
Entertainment and leisure options at the apartment include a nightclub and a casino, as well as a sundeck, a picnic area, and a golf course. Various sport options, such as darts, are provided in the area.
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Great deal
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Beach access
Sugar Shores ~ 3 Mi To Indiana Dunes Nat'L Park
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Heating
- Table tennis
The 4-bedroom Sugar Shores ~ 3 Mi To Indiana Dunes Nat'L Park Chesterton villa is located about 10 minutes by car from Prairie Duneland Trail, giving access to various tourist spots nearby. The property welcomes up to 12 guests and offers a games room for their entertainment.
The area is popular for those who like ping-pong.
Sugar Shores ~ 3 Mi To Indiana Dunes Nat'L Park
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Heating
- Table tennis
Sugar Shores ~ 3 Mi To Indiana Dunes Nat'L Park
The 4-bedroom Sugar Shores ~ 3 Mi To Indiana Dunes Nat'L Park Chesterton villa is located about 10 minutes by car from Prairie Duneland Trail, giving access to various tourist spots nearby. The property welcomes up to 12 guests and offers a games room for their entertainment.
The area is popular for those who like ping-pong.
Cheap Chesterton Vacation Rentals
Heart Of Indiana Dunes National Park With Hot Tub
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Entertainment
- Garden area
The 5-bedroom Heart Of Indiana Dunes National Park With Hot Tub Chesterton villa is located about a 10-minute drive from Coffee Creek Watershed Preserve and provides a Jacuzzi. The Chesterton holiday home hosts up to 12 guests and provides them with parking.
If you would like to stay active, try badminton, ping pong, and billiard at the Chesterton accommodation.
Heart Of Indiana Dunes National Park With Hot Tub
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Entertainment
- Garden area
Heart Of Indiana Dunes National Park With Hot Tub
The 5-bedroom Heart Of Indiana Dunes National Park With Hot Tub Chesterton villa is located about a 10-minute drive from Coffee Creek Watershed Preserve and provides a Jacuzzi. The Chesterton holiday home hosts up to 12 guests and provides them with parking.
If you would like to stay active, try badminton, ping pong, and billiard at the Chesterton accommodation.
Charming Chesterton Home: W/ Idyllic Location!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Table tennis
- Sun loungers
Up to 8 guests can stay at the welcoming Charming Chesterton Home: W/ Idyllic Location! and enjoy Coffee Creek Park, located 5 minutes' walk away. The 3-bedroom holiday home features opportunities for ping pong in the area, 3.7 km from Prairie Duneland Trail.
Charming Chesterton Home: W/ Idyllic Location!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Table tennis
- Sun loungers
Charming Chesterton Home: W/ Idyllic Location!
Up to 8 guests can stay at the welcoming Charming Chesterton Home: W/ Idyllic Location! and enjoy Coffee Creek Park, located 5 minutes' walk away. The 3-bedroom holiday home features opportunities for ping pong in the area, 3.7 km from Prairie Duneland Trail.
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Beach access
Moody Modern Dunes Hot Tub Beach And Trails
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Jacuzzi
Located 7 km from Bailly Homestead and Chellberg Farm National Park, Moody Modern Dunes Hot Tub Beach And Trails Chesterton villa offers karaoke for guests' leisure. Featuring a Jacuzzi, the 3-bedroom holiday home is suitable for 5 people.
Moody Modern Dunes Hot Tub Beach And Trails
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Jacuzzi
Moody Modern Dunes Hot Tub Beach And Trails
Located 7 km from Bailly Homestead and Chellberg Farm National Park, Moody Modern Dunes Hot Tub Beach And Trails Chesterton villa offers karaoke for guests' leisure. Featuring a Jacuzzi, the 3-bedroom holiday home is suitable for 5 people.
Pet Friendly Vacation Rentals Chesterton
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Top location
Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Staying at the 3-bedroom Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms Chesterton, guests can easily reach Chesterton Art Center, located only 7 minutes' walk away. With a maximum capacity of 9 guests, the villa offers a private parking lot.
Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms
Staying at the 3-bedroom Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms Chesterton, guests can easily reach Chesterton Art Center, located only 7 minutes' walk away. With a maximum capacity of 9 guests, the villa offers a private parking lot.
Roomy Retreat-Family & Friends 2 King Bed Game Room
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Bar/ Lounge area
- Patio
Situated merely a 13-minute walk from Chesterton Park, the 6-bedroom Roomy Retreat-Family & Friends 2 King Bed Game Room Chesterton villa entices guests to explore various tourist attractions in the area. The holiday home hosts up to 16 guests and provides them with private car parking.
Roomy Retreat-Family & Friends 2 King Bed Game Room
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Bar/ Lounge area
- Patio
Roomy Retreat-Family & Friends 2 King Bed Game Room
Situated merely a 13-minute walk from Chesterton Park, the 6-bedroom Roomy Retreat-Family & Friends 2 King Bed Game Room Chesterton villa entices guests to explore various tourist attractions in the area. The holiday home hosts up to 16 guests and provides them with private car parking.
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Best-rated
Pulaski Point Properties
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
The 6-room Pulaski Point Properties Chicago apartment offers proximity to such tourist attractions as Irving Park Lutheran Church, situated nearly 5 minutes' walk away. This apartment is also equipped with amenities like ironing facilities, a dishwasher to ensure guests' comfort.
Pulaski Point Properties
- Cookware/ Kitchen utensils
- 24-hour reception
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Pulaski Point Properties
The 6-room Pulaski Point Properties Chicago apartment offers proximity to such tourist attractions as Irving Park Lutheran Church, situated nearly 5 minutes' walk away. This apartment is also equipped with amenities like ironing facilities, a dishwasher to ensure guests' comfort.
Chesterton Vacation Rentals Oceanfront
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Guest favorite
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts
- Cookware/ Kitchen utensils
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts Chicago apartment enjoys a convenient location just an 8-minute walk from Gill Park. The apartment features Wi-Fi and public parking nearby.
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts
- Cookware/ Kitchen utensils
- Free parking
- 24-hour security
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts Chicago apartment enjoys a convenient location just an 8-minute walk from Gill Park. The apartment features Wi-Fi and public parking nearby.
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Popular choice
5430 Happy Home
- Shared kitchen
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
5430 Happy Home Chicago apartment lies about 1 km from New Philadelphia Missionary Baptist Church and approximately 5 minutes' walk from Garfield tube station. The homestay is situated within a 9-km distance of Chicago Union train station and right around the corner from Garfield & State bus station.
5430 Happy Home apartment also offers yoga, as well as yoga instruction, allowing guests to keep fit. At the apartment, guests are offered a spa bath.
5430 Happy Home
- Shared kitchen
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Garden area
5430 Happy Home
5430 Happy Home Chicago apartment lies about 1 km from New Philadelphia Missionary Baptist Church and approximately 5 minutes' walk from Garfield tube station. The homestay is situated within a 9-km distance of Chicago Union train station and right around the corner from Garfield & State bus station.
5430 Happy Home apartment also offers yoga, as well as yoga instruction, allowing guests to keep fit. At the apartment, guests are offered a spa bath.
2F Chicago'S Little Italy Near West Loop & Downtown
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Leisure/ TV room
- Laundry
Situated a 6-minute walk from Arrigo Park, the spacious 2F Chicago'S Little Italy Near West Loop & Downtown Apartment offers proximity to various nearby tourist attractions. This apartment can host up to 8 guests.
2F Chicago'S Little Italy Near West Loop & Downtown
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Leisure/ TV room
- Laundry
2F Chicago'S Little Italy Near West Loop & Downtown
Situated a 6-minute walk from Arrigo Park, the spacious 2F Chicago'S Little Italy Near West Loop & Downtown Apartment offers proximity to various nearby tourist attractions. This apartment can host up to 8 guests.
Chesterton Vacation Rentals with Private Pool
The Avondale Guesthouse
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Offering a terrace and a picnic area for an enjoyable stay, The Avondale Guesthouse Chicago villa is within a 300-metre distance of Algonquin Park.
The Avondale Guesthouse
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
The Avondale Guesthouse
Offering a terrace and a picnic area for an enjoyable stay, The Avondale Guesthouse Chicago villa is within a 300-metre distance of Algonquin Park.
Irving Park Updated Vintage Top Unit 2-Flat
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
The 93 m² Classic Chicago Upstairs Apt Private Balcony is located around 6 km from the baseball stadium "Wrigley Field" and just a 7-minute walk from Park View Lutheran Church. Wi-Fi and a car park are provided for guests' utmost comfort.
Irving Park Updated Vintage Top Unit 2-Flat
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
Irving Park Updated Vintage Top Unit 2-Flat
The 93 m² Classic Chicago Upstairs Apt Private Balcony is located around 6 km from the baseball stadium "Wrigley Field" and just a 7-minute walk from Park View Lutheran Church. Wi-Fi and a car park are provided for guests' utmost comfort.
1F Cozy Home In Little Italy Near Downtown West Loop United Center
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Situated within a 500-metre distance of Arrigo Park, the spacious 1F Cozy Home In Little Italy Near Downtown West Loop United Center Chicago apartment looks out onto the city. This apartment can host up to 6 guests.
1F Cozy Home In Little Italy Near Downtown West Loop United Center
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
1F Cozy Home In Little Italy Near Downtown West Loop United Center
Situated within a 500-metre distance of Arrigo Park, the spacious 1F Cozy Home In Little Italy Near Downtown West Loop United Center Chicago apartment looks out onto the city. This apartment can host up to 6 guests.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Chesterton, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Blue Birdhouse - Indiana Dunes - Pet Friendly |
9.3 / 10 (35 Reviews) |
From 139$ | |
| Your Midwest Dunes Vacation Tri-State Paradise! |
9.7 / 10 (9 Reviews) |
From 228$ | |
| Dunes Home 3 Bedroom I 2 Baths I 2 Living Rooms |
8.1 / 10 (27 Reviews) |
From 148$ | |
| Roomy Retreat-Family & Friends 2 King Bed Game Room |
8.3 / 10 (7 Reviews) |
From 472$ | |
| Pulaski Point Properties |
9.7 / 10 (149 Reviews) |
From 53$ |
Frequently Asked Questions
Which vacation rentals in Chesterton are close to downtown?
Consider staying at 2F Chicago's Little Italy Near West Loop & Downtown. It offers comfortable lodging just minutes from downtown, providing easy access to restaurants and shops. The Dunes Home 3 Bedroom is another good option in the heart of Chesterton.
Book your stay during the week to enjoy better pricing and less crowded attractions.
What are pet-friendly vacation rentals in Chesterton?
You can check out Blue Birdhouse - Indiana Dunes which welcomes pets. It allows you to enjoy the natural surroundings with your furry friend. Sugar Shores offers additional space and pet-friendly features.
Notify the rental owner about your pet ahead of arrival to ensure a smooth check-in process.
Which vacation rentals near the Indiana Dunes are best for outdoor enthusiasts?
Heart Of Indiana Dunes National Park With Hot Tub offers a great retreat for nature lovers. You can explore hiking trails and enjoy the hot tub afterward. Moody Modern Dunes Hot Tub Beach And Trails is also nearby for beach access.
Visit Indiana Dunes early in the morning to find parking easily and beat other visitors at popular spots.
What are the best vacation rentals in Chesterton for families?
Roomy Retreat-Family & Friends 2 King Bed Game Room is perfect for bigger families. It offers enough space and entertainment options. Dunes Home 3 Bedroom is another family-friendly option with comfortable amenities.
Plan your family's visit during weekdays to enjoy less crowded attractions and better service.
Which budget-friendly vacation rentals are available in Chesterton?
Pulaski Point Properties offers affordable rates without sacrificing comfort. 5430 Happy Home is another budget option that provides good value for money. Both are great for travelers on a budget.
Book directly with the rental owner to avoid extra fees from booking platforms.
Are there any vacation rentals in Chesterton with hot tubs?
The Heart Of Indiana Dunes National Park With Hot Tub comes equipped with a hot tub for relaxation after a day of exploring. Moody Modern Dunes Hot Tub Beach And Trails also offers hot tub amenities near the beach.
Check listings for access to hot tubs year-round, especially during colder months for a cozy experience.
Which Chesterton vacation rentals offer two bedrooms for groups?
Double Play Wrigley - Prime Location Across From Wrigley Field & Transit - 2Br Apts is an excellent choice for groups. It provides ample space with two bedrooms. Roomy Retreat-Family & Friends 2 King Bed Game Room is another option with generous space.
Book well in advance to secure two bedroom rentals, especially during peak travel seasons.
What unique events happen in Chesterton throughout the year?
Chesterton's European Market runs each Saturday from May to October, showcasing local vendors and artisan goods. Additionally, the Chesterton Art Fair in late summer features local artists and crafts.
Arrive early for the best selection at the European Market, especially on busy mornings.
How can I get around Chesterton efficiently during my stay?
Renting a car is the most convenient option for exploring Chesterton and nearby attractions. Public transportation options are limited; however, some rentals are close to popular sites.
Use major routes like U.S. 20 for quick access to Duneland Beach and Indiana Dunes National Park.
What should I know about safety in Chesterton?
Chesterton is generally safe, particularly in busy areas such as downtown. However, it's wise to stay aware of your surroundings, especially at night in less populated areas.
Stick to well-lit paths when walking at night and travel in groups whenever possible.