Planning a getaway with family or friends and want everyone close together — without giving up comfort or convenience? We’ve got just the spot. We’re proud to manage two gorgeous homes in the Trailside neighborhood, perfectly situated for relaxation, outdoor adventure, and easy access to all the best South Haven has to offer.
Whether you're coordinating a family reunion or a group retreat, this neighborhood gives you the option to book one or both homes so your group can spread out while still staying steps apart.
Resort-Style Amenities for a Stress-Free Stay
This neighborhood offers thoughtful features that turn an ordinary vacation into a memorable one:
🏊♀️ Community Pool & Clubhouse
Spend sunny afternoons lounging by the pool, or gather at the clubhouse for a relaxed hangout or ping pong tournament. It’s perfect for unwinding after a day of exploring South Haven.
🚴♀️ Next to the Van Buren Trail
Bring your bikes, lace up your walking shoes, or head out for a morning jog — the Van Buren State Park Trail sits right next door. This scenic route connects you to miles of nature, dunes, and forest, ideal for adventurers of all ages.
Properties
Anchor Point Vacation Rentals currently manages two beautiful vacation homes within the Trailside neighborhood. Having multiple homes in the same neighborhood gives guests even more flexibility when booking a stay. Whether you're coordinating multiple families or looking for homes within walking distance of one another, these properties make travel planning simple and stress-free.
1. Trailside Treasure
Newly constructed in 2023, the nautical decor was thoughtfully curated for your beach vacation. Three stories of living space and 2 living rooms offer guests the option to spread out or gather together in the open kitchen/family room. The home sits steps away from a community pool.
5 Bedrooms, 4.5 Bathrooms, Sleeps 16 people.
2. All In at Trailside
Your group will be “All In” for this South Haven retreat! This inviting ranch-style home offers something for everyone—steps to a neighborhood pool plus hiking and biking trails that connect you to downtown or Van Buren State Park. With 2 living rooms, the lower level features a game room with shuffleboard, a wet bar, and extra sleeping space. The backyard is perfect for gathering around the fire pit, grilling out, or playing yard games. Walk to Kids Corner Park and the Blue Stairs at South Beach or take a quick ride just over a mile into downtown South Haven.
5 Bedrooms, 3 Bathrooms, Sleeps 14 people.
Unbeatable Location Near Lake Michigan & Downtown
Here, convenience isn’t just a perk — it’s a lifestyle.
🌊 Just 0.5 Miles to Blue Stairs Beach Access
A quick, easy walk leads you to one of the most beloved beach access points along Lake Michigan. Expect sweeping shoreline views, stunning sunsets, and plenty of space to play and relax.
🛍️ Only 1 Mile to Downtown South Haven
Browse shops, enjoy waterfront dining, grab ice cream, or attend seasonal festivals — downtown South Haven is overflowing with charm, and it’s just a short trip from your doorstep.
Perfect for Large Groups — Rent One or Both Homes
Traveling with a bigger crew? Rent one home for a cozy retreat, or reserve both houses for a spacious, convenient multi-home stay. It’s a great setup for:
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Multi-generational family trips
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Friends’ getaways
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Wedding groups
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Holiday gatherings
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Summer vacations
Everyone gets their own space while staying close enough to enjoy every moment together.
Your South Haven Adventure Starts Here
From beach days and trail rides to poolside relaxing and downtown exploring, the Trailside neighborhood gives you the best of South Haven in one perfectly placed location. With two beautiful homes available — planning your next group getaway has never been easier.
Ready to bring everyone together in South Haven?
We’re here to help you choose the perfect setup for your stay.
