A lighthouse and pier at sunset.

Three Oaks Vacations from $513

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Your Three Oaks Vacation

Book a Three Oaks vacation package and get ready for an awesome adventure. With a reputation for its rich history and spectacular views, there's plenty to keep you on the move in this city. You'll want to do some exploring during your trip to Three Oaks. Don't miss popular attractions like Four Winds Casino New Buffalo, The Acorn and Townline Beach. Expedia can help you escape your daily routine. Tailor your vacation to Three Oaks to suit your travel style, whatever that may look like.

The Latest Three Oaks Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A sign for Ivy Court Inn & Suites surrounded by lush greenery and white hydrangea flowers.
    Jan 8 - Jan 11

    Ivy Court Inn & Suites + Flight

    South Bend
    3 nights
    2.5 star property
    9.2/10 - Wonderful (999 reviews)
    "Very convenient location near Notre Dame Campus. I found it cheaper to book thru a 3rd party site. Breakfast offering was exceptional. Real scrambled eggs as opposed to watery powdered eggs at hotel chains. Also included fried eggs over easy at the buffet. Downside, the elevator was out of order and I was on the 3rd floor."
    Reviewed October 28, 2026
    Roundtrip • Boston (BOS) - South Bend (SBN)
    BOS - SBN • 1 stop SBN - BOS • 1 stop
    $592
    $513
    per traveler
    found 1 day ago
    Ivy Court Inn & Suites
  • A spacious lobby with a central bar area, multiple seating arrangements, and a staircase leading to an upper level.
    Jan 8 - Jan 11

    The Inn at Saint Mary's + Flight

    South Bend
    3 nights
    3.5 star property
    9.4/10 - Exceptional (1,385 reviews)
    Roundtrip • Boston (BOS) - South Bend (SBN)
    BOS - SBN • 1 stop SBN - BOS • 1 stop
    $823
    $681
    per traveler
    found 1 day ago
    The Inn at Saint Mary's
  • A person holding a glass of dark liquid, likely coffee, on a deck overlooking a swimming pool.
    Jan 8 - Jan 11

    Pool Kayaks Hot Tub Game Rooms Sleeps 16 + Flight

    Keller Park
    3 nights
    2.0 star property
    Roundtrip • Boston (BOS) - South Bend (SBN)
    BOS - SBN • 1 stop SBN - BOS • 1 stop
    $1,512
    $1,268
    per traveler
    found 18 hours ago
    Pool Kayaks Hot Tub Game Rooms Sleeps 16
  • A modern house with a pool, outdoor seating, and a wooden staircase.
    Jan 8 - Jan 11

    Pool Hot Tub 5 min to ND Coffee Bar Games + Flight

    South Bend
    3 nights
    2.0 star property
    Roundtrip • Boston (BOS) - South Bend (SBN)
    BOS - SBN • 1 stop SBN - BOS • 1 stop
    $1,280
    $1,093
    per traveler
    found 1 day ago
    Pool Hot Tub 5 min to ND Coffee Bar Games
  • A hotel entrance with a covered walkway, large windows, and a landscaped area with potted plants.
    Jan 8 - Jan 11

    Hilton Garden Inn South Bend + Flight

    South Bend
    3 nights
    3.0 star property
    9.0/10 - Wonderful (568 reviews)
    Roundtrip • Boston (BOS) - South Bend (SBN)
    BOS - SBN • 1 stop SBN - BOS • 1 stop
    $770
    $659
    per traveler
    found 18 hours ago
    Hilton Garden Inn South Bend

Where to stay near Three Oaks

Three Oaks offers a charming escape for outdoor enthusiasts and families alike. With its scenic landscapes and adventure-filled activities, it's perfect for a fall trip. Enjoy a great stay in close proximity to delightful neighborhoods that exude a family-friendly and romantic atmosphere.
A lighthouse on a sandy beach with a rocky breakwater and a cloudy sky.

New Buffalo

For families and weekend getaway seekers wanting a memorable trip, New Buffalo offers a delightful blend of nature and recreation. With its stunning beach, scenic state park, and engaging attractions like the New Buffalo Railroad Museum, visitors can enjoy both relaxation and adventure. Located about 7 miles by car from Three Oaks, New Buffalo is an ideal base for exploring the great outdoors. Booking your stay here ensures a vibrant and enjoyable experience in this charming lakeside city.

A sunset over a body of water with two tents on a grassy field.

Lakeside

Experience the charm of Lakeside, an excellent hub for families and outdoor enthusiasts seeking a scenic getaway. With its stunning beaches and the nearby Warren Dunes State Park, Lakeside offers a perfect mix of relaxation and adventure. Enjoy recreational areas and playgrounds that cater to all ages, enhancing your family vacation. Located about 5 miles by car from Three Oaks, Lakeside is a smart choice for travelers looking to unwind and explore the beauty of Michigan's coast.

A coastal beach with kayaks and a clear view of the ocean.

Union Pier

If you are a couple or family seeking a memorable getaway, look no further than Union Pier, known for its breathtaking scenery and outdoor adventures. Enjoy the tranquil beauty of nearby Warren Dunes State Park and unwind at the picturesque New Buffalo Public Beach, perfect for sun-soaked days. With recreational areas and playgrounds for the kids, Union Pier offers a delightful experience for nature lovers. It's only about a 5 miles drive from Three Oaks, making it a smart choice for your vacation stay.

A lighthouse at sunset with a colorful sky and calm water.

Sawyer

Ideally situated for outdoor enthusiasts and families, Sawyer offers a gateway to stunning attractions like Warren Dunes State Park and Cherry Beach, perfect for relaxation and adventure. With its recreational area and playground, there's something for everyone to enjoy. Just about 6 miles by car from Three Oaks, Sawyer makes for an easy getaway, making it a smart choice for your vacation stay. Experience the natural beauty and vibrant activities that make Sawyer a delightful retreat.

Gordon Beach

Travelers visiting the area often choose Gordon Beach, especially families and couples seeking a blend of outdoor adventure and scenic beauty. This charming village offers access to stunning attractions like the New Buffalo Public Beach and the expansive Warren Dunes State Park, perfect for leisurely days by the water or exploring nature trails. Located about 5 miles by car from Three Oaks, Gordon Beach provides a welcoming atmosphere for a memorable getaway, making it an ideal choice for your vacation stay.

Discover the most popular places to visit in Three Oaks

A branch with green leaves and acorns against a clear blue sky.

The Acorn

This intimate 250-seat theater in a historic corset factory offers exceptional acoustics for diverse performances. Enjoy local brews while experiencing up-close connections with renowned and emerging artists.
See properties

Three Oaks Hotel Deals

A hotel with a large parking lot, a central courtyard, and a building with a distinctive curved roof.

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
5.2 mi from Three Oaks
9.4 out of 10, Exceptional, (2,340 reviews)
$109 nightly
The price is $115
Nov 5 - Nov 6
Total with taxes and fees
Four Winds Casino Resort – New Buffalo
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.
See all properties in Three Oaks

Frequently Asked Questions

How much does a Three Oaks vacation package cost?

You can grab a vacation package to this top destination from $513 on Expedia. However, how much your vacation to Three Oaks costs will depend on the season, length of stay and hotel choice.

What are the cheapest months to go to Three Oaks?

November, December and January are great times to search for cheap Three Oaks vacation packages. Opting to travel in less busy months means you can generally find reduced prices on flights and hotels.

How many days is enough for Three Oaks?

You can see all the main sights in Three Oaks in a few days, including the popular Vickers Theatre. If you're looking for a longer Three Oaks vacation, look at what kind of excursions and activities are available in the area.

Is it worth booking a vacation package to Three Oaks?

Three Oaks has everything you need for a wonderful getaway. Begin your Three Oaks vacation on a high note by visiting top attractions like The Acorn.

How to find the best Three Oaks package deals?

Use Expedia's filter tool to find some tempting Three Oaks package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Three Oaks package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.

Is it cheaper to book a Three Oaks vacation as a package?

An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can tailor your Three Oaks escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

When to book a vacation package to Three Oaks?

Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Three Oaks break.

Does Expedia offer Book Now, Pay Later Three Oaks vacation packages?

Set off on your perfect escape to Three Oaks with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snap up travel deals while they last.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.