House holiday rentals in Paw Paw Lake

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

Dog-Friendly Lake-View Cottage Near Wineries

Less than 2 hrs from Chicago & a short walk to Little Paw Paw Lake, enjoy the charming vibes of our quaint and completely private cottage. With a stunning view of the lake, indoor/outdoor fire areas, and a serene yard, our home is perfect for a weekend away, a Michigan staycation, or even as an overflow home when visiting family. Our cottage exudes old charm with its rustic hardwood floors and cabin-like porch, yet it has the right amount of modernity with high-speed WiFi and newer appliances.

Modern Secluded Cabin, Private Hot Tub, Fire Pit

Escape to this charming cabin in the woods. Relax in total privacy and peace and quiet with majestic views of towering trees. Natural sunlight floods into the home creating a healthy environment to unwind in. Stay warm and cozy with heated concrete floors and a gas fireplace. Cook in the well stocked kitchen. Soak away your worries in the private hot tub. Roast s’mores in the backyard fire pit and grill on the huge deck. Fun awaits in the 3-season game room in barn NOT HEATED. Dog friendly.

Hot tub & sauna, pet friendly, 1/2m to Hagar Beach

Peaceful, newly renovated 1930’s cabin walkable (1/2 mile) to Hagar Beach in the heart of SWMI. This pet-friendly home has a cozy feel with an outdoor hot tub, sauna, & fully-furnished spaces perfect for a relaxing getaway, remote work, or staycation home base while you explore the lake, bike trails, breweries, & eateries. Enjoy a quiet, off-the-beaten path stay close to everything Lake Michigan offers featuring a stocked kitchen, cozy reading nook & desk, and outdoor dining & fire pit.

TRYON FARM MID-MODERN SPA IN THE WOODS

Come, enjoy our Tryon Farm modern spa. A Sustainable luxurious open concept tree-house in the woods. Minutes from the beach with an outdoor sauna, Hottub, shower, and Mr. Steam. Perfect for two or a family/group adventure. A true destination with Yoga studio, Mirror by LuLu lemon and wellness elements. The house is a perfect balance of art and nature and luxury and spiritual. Treat yourself to a farm to table, hand made, locally sourced chef services for an extra special experience.

Updated Cozy Cottage Near Lakes, Wineries & Trails

Deer Cottage is a warm and cozy retreat near Big & Little Paw Paw Lakes—perfect for a romantic getaway or family stay. This renovated lake home sleeps 4 with a queen bed and sleeper sofa, a fully remodeled kitchen and bath, indoor gas fireplace, and 2 smart TVs. Just a short drive away, guests can explore nearby wineries, kayak the river, or relax at Lake Michigan. Indy grandparents created this sweet escape to be near their granddaughters—complete with deer sightings right from the yard.

A Home with a Forest Scent and the Sound of Waves

Escape to Pure Michigan! This charming home is a short walk to Hagar Beach and just a quick 10-minute drive to Silver Beach. Love golf? Tee off at Harbor Shores, Lake Michigan Hills, or Paw Paw Lake Golf Club. Sip and savor at Contessa Wine Cellars and Filkins Vineyards, or pick fresh fruit at Jollay Orchards and Fruit Acres Farm—all just a short 15-minute drive or less! After a day of adventure, relax by the cozy outdoor fireplace—the patio glows beautifully at night with string lights.

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

Great Paw Paw Lake Getaway - Close to Beaches!

Beautiful updated home is perfect for families with upstairs and downstairs sleeping space. Upstairs has a spacious master bedroom with 1 king bed and sofa bed and a master bath. Bedroom 2 boasts 2 twin size beds as well as bedroom 3 (2 twin beds). Downstairs has a spacious kitchen & living area with 2 futon beds. Outside a spacious patio with fire pit close by. Home is close to Jollay Orchards & Contessa Wine Cellars. Beautiful St. Joseph and Silver Beach are 20 minutes away.

LakeMichigan•Beach•Hot Tub•Sauna•Amazing Views

Welcome to Spyglass! If you are looking for a perfect place for that a visit to Lake Michigan any time of year, then The Spyglass has you coved. Whether you’re there for couple's retreat, family vacation or girlfriend’s weekend this gorgeous Lake front property with private beach has it all. Being located not too far off the beaten path, only 5 minuets to downtown St. Joseph the Spyglass is a perfect landing zone for all the nearby activities Southwest Michigan has to offer.

Family Friendly Private Beach Home with Hot Tub

5 min walk to Private Beach 10 min drive to Downtown South Haven 18 min drive to Downtown Saugatuck Escape to our 3BR South Haven home in an exclusive community, just a 5-min walk to a private Lake Michigan beach. Comfortably sleeps 8. Features a private hot tub, chef's kitchen, and cozy fireplace. Perfect for families, you're just a short drive from downtown South Haven & Saugatuck. Your luxurious lakeside retreat awaits! Experience South Haven With Us & Learn More Below!

Frank Lloyd Wright’s Eppstein House

Designed by Frank Lloyd Wright, the Eppstein House is a rare architectural gem nestled in the same region as Wright’s Meyer May House in Grand Rapids, the Gilmore Car Museum in Hickory Corners, and the charming beach town of South Haven. This is a unique opportunity to experience an extraordinary home—yours to enjoy for a few unforgettable days. Travel + Leisure named the Eppstein House as Michigan’s most unique Airbnb, effectively ranking it #1 in uniqueness for the state.