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Find Romantic Hotels in Chesterton, IN from $58

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Top Chesterton Romantic Hotels

Blue Chip Casino Hotel and Spa

3.5 star property
Michigan City
8.2 out of 10, Very Good, (1862)
"Great staff, nice room"
United States
Tina Marie
$108 nightly
The price is $121
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blue Chip Casino Hotel and Spa

Four Winds Casino Resort – New Buffalo

3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1637)
"Great place, hotel room is very well appointed. "
United States
Stuart
$109 nightly
The price is $115
Dec 8 - Dec 9
Total with taxes and fees
Four Winds Casino Resort – New Buffalo

The Brewery Lodge Hotel

3.5 star property
Michigan City
9.0 out of 10, Wonderful, (788)
"Great place to stay"
United States
James
$114 nightly
The price is $125
Dec 8 - Dec 9
Total with taxes and fees
The Brewery Lodge Hotel

Rodeway Inn

2.5 star property
Portage
7.0 out of 10, Good, (792)
"Clean room, nice staff"
United States
Marcelo
$52 nightly
The price is $58
Dec 14 - Dec 15
Total with taxes and fees
Rodeway Inn

Ameristar Casino Hotel East Chicago

4.0 star property
East Chicago
8.6 out of 10, Excellent, (1006)
"Great stay in clean modern room."
United States
Douglas
$107 nightly
The price is $120
Jan 5 - Jan 6, 2026
Total with taxes and fees
Ameristar Casino Hotel East Chicago

Home2 Suites by Hilton Merrillville

3.0 star property
Merrillville
9.0 out of 10, Wonderful, (1001)
"The staff was very friendly. "
United States
Jennifer
$87 nightly
The price is $98
Dec 21 - Dec 22
Total with taxes and fees
Home2 Suites by Hilton Merrillville

Pine Lake Resort and Banquets

2.5 star property
La Porte
6.8 out of 10, (582)
"Great stay"
United States
Tiffany
$79 nightly
The price is $91
Dec 8 - Dec 9
Total with taxes and fees
Pine Lake Resort and Banquets

Michigan City Inn

Michigan City
4.6 out of 10, (1000)
"Good area to stay for Indiana Dunes or beach. Hotel needs some new carpet and paint and would be a great place to stay."
United States
Ryan
$90 nightly
The price is $101
Dec 8 - Dec 9
Total with taxes and fees
Michigan City Inn

On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

Michigan City
9.6 out of 10, Exceptional, (77)
"House was very clean and not too far from the beach. Loved sitting on the porch listening to the water. Will definitely be booking again next year. "
United States
Rebecca B.
$502 nightly
The price is $510
Dec 8 - Dec 9
Total with taxes and fees
On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views

Modern Farmhouse steps from downtown New Buffalo & Lake Michigan!

Downtown New Buffalo
10.0 out of 10, Exceptional, (181)
"Our third stay at this property. It just gets better every year! "
United States
Richard H.
$1,000 nightly
The price is $1,053
Dec 31 - Jan 1, 2026
Total with taxes and fees
Modern Farmhouse steps from downtown New Buffalo & Lake Michigan!
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.

Find out more about Chesterton

Chesterton attractions for couples

Chesterton, Indiana, offers a delightful blend of natural beauty and local charm that adventurous travelers will appreciate. Start your exploration at the Indiana Dunes National Park, where miles of sandy beaches and scenic trails await. Families can enjoy a day of swimming, hiking, or picnicking while soaking up stunning views of Lake Michigan. For a taste of local culture, visit the Chesterton European Market, held every Saturday, where you can find artisanal goods, fresh produce, and unique crafts that showcase the town's vibrant community spirit. Don't miss the opportunity to explore the nearby Coffee Creek Watershed Preserve, a serene area perfect for walking, birdwatching, or simply enjoying the tranquility of nature. History enthusiasts will love the Old Chesterton Train Depot, which now houses a museum that offers insights into the town's rich past. After a full day of adventure, consider staying in the cozy accommodations along the main strip, where local hotels provide attentive service and comfortable amenities, ensuring your family feels pampered and cared for. Here, you'll find the perfect home base to unwind and plan your next day's adventures!

Find the best romantic hotels in Chesterton

For couples looking to escape to the charming town of Chesterton, Indiana, these hotels provide a perfect blend of comfort and romantic amenities. Each option offers a unique atmosphere to create special memories together.

Spring House Inn

  • Why it's great for a couples retreat: Spring House Inn is an ideal choice for travelers seeking a romantic getaway, a guest review rating of 8.6. With private hot tubs and balconies, couples can enjoy intimate moments while taking in the tranquil surroundings. The hotel also offers complimentary breakfast, perfect for starting the day together before exploring the nearby beach or indulging in room service for a cozy night in.
  • Other amenities: Additional amenities include an indoor pool for refreshing swims, a terrace for serene evenings, and off-street parking for convenience. Guests can also benefit from fitness facilities to maintain their routine while away, and the added luxury of champagne service to toast their special moments. This charming inn creates a welcoming place for couples looking to unwind and connect.
  • Nearby attractions: Indiana Dunes National Park - 0.54 miles, Chellberg Farm - 0.7 miles, Cowles Bog Trailhead - 1.97 miles

Hilton Garden Inn Chesterton

  • Why it's great for a couples retreat: Hilton Garden Inn Chesterton presents a lovely ambiance for romantic retreats, with an excellent guest review rating of 8.6. Couples can enjoy spacious suites featuring separate living areas, ideal for cozy evenings together. The hotel’s indoor pool and fitness facilities add a touch of leisure to their stay, while the restaurant offers options for delightful dining experiences.
  • Other amenities: Additional amenities include a terrace for enjoying fresh air, free self-parking for convenience, and designer toiletries for a touch of luxury. With a microwave and refrigerator in suites, guests can easily prepare snacks or keep beverages cool, making it an inviting choice for couples looking to create a memorable escape.
  • Nearby attractions: Lustron House - 2.65 miles, Coffee Creek Watershed Conservancy Preserve - 0.3 miles

Best Western Indian Oak

  • Why it's great for a couples retreat: Best Western Indian Oak offers a cozy setting perfect for romantic escapes, with a solid guest review rating of 8.4. The hotel features stunning waterfront views, allowing couples to enjoy peaceful sunsets together. Guests can indulge in complimentary breakfast before relaxing in the indoor pool or taking a stroll to the nearby sandy beach.
  • Other amenities: Other enticing features include a sauna and steam room for unwinding together, along with a fireplace in select rooms for cozy evenings. The hotel also offers free onsite parking and daily housekeeping, ensuring a straightforward experience. With nearby golf options and a lovely lake view, this hotel is a charming spot for couples looking to connect and relax.
  • Nearby attractions: Lustron House - 1.19 miles, Wykes-Plampin Nature Preserve - 1.54 miles, Indiana Dunes Visitor Center - 1.82 miles

Waterbird Lakeside Inn

  • Why it's great for a couples retreat: Waterbird Lakeside Inn is a charming option for couples seeking a peaceful retreat, with a guest review rating of 7.4. Located by the serene lake, it offers lakeside views that create a romantic atmosphere. Guests can enjoy a relaxing time on the balcony, soaking in the tranquil surroundings and sharing quiet moments together.
  • Other amenities: This intimate inn also provides complimentary toiletries and free self-parking for added convenience. The air-conditioned rooms ensure comfort, while the scenic location invites couples to explore the beauty of nature together. With its cozy ambiance, Waterbird Lakeside Inn is a delightful choice for those looking to escape the hustle and bustle of everyday life.
  • Nearby attractions: Lustron House - 1.16 miles, Wykes-Plampin Nature Preserve - 1.53 miles, Indiana Dunes Visitor Center - 1.81 miles

Comfort Inn & Suites Porter near Indiana Dunes

  • Why it's great for a couples retreat: Comfort Inn & Suites Porter provides a comfortable setting for romantic getaways, featuring a guest review rating of 7.2. Couples can relax in the indoor pool or unwind in the hot tub, making it an ideal spot to enjoy leisurely moments together. With complimentary breakfast included, couples can start their day off right before heading out to explore the nearby Indiana Dunes.
  • Other amenities: Additional amenities include free self-parking for convenience, daily housekeeping, and microwaves in rooms for late-night snacks. The hotel also features fitness facilities and accessible amenities, ensuring a comfortable stay for all guests. This inviting hotel allows couples to create lasting memories while enjoying the beauty of the surrounding area.
  • Nearby attractions: Indiana Dunes National Park - 1.01 miles, Chellberg Farm - 1.77 miles, Cowles Bog Trailhead - 3.05 miles

Top Chesterton Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Chesterton?
Are you looking for a romantic vacation? Our guests also enjoy Chesterton for its shopping, restaurants, and beaches. If you'd like to explore some of the area's notable sights, you might make a stop by Lake Michigan, Lustron House, or Chellberg Farm. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chesterton?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chesterton: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chesterton?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all that Chesterton has to offer. Couples looking for a little of everything will enjoy Chesterton for its beaches, lakeside setting, and restaurants. Lake Michigan, Lustron House, and Chellberg Farm are worth a stop when you're out and about.
What's the best way to get to Chesterton and around town during my romantic getaway?
These transportation options in Chesterton might help your romantic trip get off to a smooth start: To get to Chesterton, you can fly into Chicago Midway Airport (MDW), which is the closest major airport, located 37 mi (59.6 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.

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