
Holiday houses in Dewey Lake
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Top-rated holiday rentals in Dewey Lake
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Peaceful Cable Lake Getaway w/ Dock & Views
Escape to easygoing lake life at this cozy 2-bedroom, 2-bath cabin on beautiful Cable Lake. Perfect for families or friends, this well-equipped retreat offers peaceful views year-round, plus direct lake access for fishing, boating, or simply relaxing by the water. Spend your mornings on the screened porch, your afternoons on the lake, and your evenings by the fireplace or grill. Local wineries are just a short drive away, and St. Joseph makes a fun day trip. Why you’ll love it: - Private backyard with lake access & stunning views - Open, modern living space with fireplace & lake-facing windows - Fully stocked kitchen + wine/beverage cooler - Deck, patio furniture, Adirondack chairs & life vests - Sleeps up to 6 with a loft for extra space - Easy parking for up to 3 vehicles Whether you’re here to unwind or explore Southwest Michigan, this lakefront cabin is the perfect place to slow down and enjoy it all.

Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.
Welcome to the our Lake Retreat "The Toasted Marshmallow" and B&P Getaways where we have 5 unique lake homes in the Sister Lakes area. Please click on my profile picture twice to check them out. We have them in all sizes. Inquire about our private chefs, boat captains, wine tours, yoga instructor, massage therapist, boat rental and concierge services. We will help you make a fun, memorable and enjoyable trip. from a Family trip to your bachelorette party. book today! Inquire before booking

-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.

Chiper Days on Magician Lake w/Dock and kayaks
Relax & Recharge at Our Updated Lake House Retreat at Sister Lakes with Lake Access . Welcome to your perfect escape! Only 1.5/2 hour drive from Chicagoland. Close to beach towns, breweries, trails, and wineries Relax on the patio, firepit area, built-in beds, open living area, dockside, or on the 500-acre all sports Magician lake. Enjoy swimming, kayaking, boating, fishing, or just taking in the view. Spend your days lounging lakeside and your nights stargazing by the fire pit or playing games.

Riverfront Oasis with Private Boat Dock
Welcome to your Riverfront Getaway – Escape to this charming two-bedroom riverfront retreat, where relaxing water views are always within reach. Enjoy your morning coffee or evening sunsets from the spacious decks overlooking the river. Unwind on the large patio or bring your boat and take advantage of the private dock. Perfect for couples, families, or friends looking for a peaceful waterfront getaway with all the comforts of home. Firepit and outdoor dining by the water. Book your stay today!

Panoramic Views/Beach/Hot Tub/Sauna/Cold Plunge
Welcome The Windover! • Private Beach • Panoramic Lake Michigan Views • Hot Tub, Sauna, Cold Plunge, Outdoor Shower •Expansive Yard /Outside Activities • 4 minutes to downtown St. Joseph, The Benton Harbor Arts District, and Harbor Shores • Centrally located Close to 6 Local Beaches Fine and Casual Dining World Class Golfing Wineries Breweries Nature Parks Mountain Bike Trail Park 1/4 from Property Curious Kids Museum Compass Fountain Silver Beach Carousel St. Joseph Lighthouse

Magician Lakehouse Escape
This Magical Lakeside Escape offers a perfect blend of luxury and comfort, making it an ideal destination for relaxation. Take a stroll on the private dock, swim in the sandy bottom waters, or kayak the shoreline. The spacious living area offers panoramic views, with breath taking sunsets. Enjoy cozy evenings by an indoor or outdoor fire. Spend the day on a (rentable) pontoon. Experience the magic of lakeside living at the newly updated Magician Lakehouse and create unforgettable memories.

Christmas Tree Farm - Evergreen Escape
Welcome to our cozy Christmas Tree Farm Airbnb – where the magic of the holiday season lasts all year round! Nestled amidst the trees, this festive retreat offers a unique getaway for guests seeking a merry escape. Whether you're here for a winter wonderland experience or a summertime retreat, our Christmas Tree Farm Airbnb welcomes guests with open arms, making every season feel like a holiday. Come make memories, unwind, and experience the charm of year-round Christmas enchantment.

Family Lake Getaway • 3BR • Near Beach & Wineries
❄️🐟🎰🍷🍺🏖️☀️ Sister Lakes Escape Gather your people and unwind, to our 3 bedroom retreat. 3 mins walk to Cable Lake and close to wineries, breweries, and charming Dowagiac. Perfect for families, couples, or friend groups looking for an easy getaway with space to relax, explore, and reconnect. Filled with Lakehouse character! ✔ Walk to Cable Lake ✔ Close to wine trail & breweries ✔ Easy drive from Chicago, South Bend & St. Joseph ✔ Sleeps 8 comfortably Book your dates now!

The Wildwood Cottage, private lake access
New for summer 2023, private lake access across the street on Little Crooked Lake! Peaceful, 2-bedroom cottage in the heart of Sister Lakes, Michigan. Fully renovated in 2021, this cottage features a large deck overlooking trees and a partial view of Little Crooked Lake. Eat-in kitchen, Weber charcoal grill, Adirondack chairs, and patio dining for 6. Walking distance to The Strand and Sister Lakes Brewing Company. 17 miles to Lake Michigan and 30 miles to Notre Dame.

Peaceful and Spacious Cottage Surrounded by Nature
Spacious 3BR & 3BA Cottage located just a short walk to the calm Cable Lake. Relax and unwind in this surrounded by nature house. Enjoy BBQ-ing, sitting by the outdoor firepit, outdoor dining or sipping your favorite beverage at the fully screened porch overlooking the forest. Cable Lake is a motor-boat free lake which makes it very peaceful and family friendly. Enjoy a swim or a kayak escapade (complimentary 2-person kayak and 2 kids kayak available to our guests).

Pontoon Included *5/1/26-10/12/26* MI Getaway
This 1100 SF 3 bed/2 bath home is perfect for your multi-family or individual stay. It is located on 40 feet of water frontage on Magician Lake. A pontoon boat is included in the rental from May to mid-October. Additional private/walk-in lake access for all Bay properties is just down the street. Fish off the dock, take the boat for a few laps around the lake, or anchor at Hemlock island and enjoy the shallow waters surrounding it!
Popular amenities for Dewey Lake holiday rentals
Other great holiday rentals in Dewey Lake

Lorlee - A Large and Luxurious Lakefront Cottage!

Lake Home w/ Amazing Views

Cabin in the woods

Modern Amish Country Tiny Home w/ Outdoor Shower

The Tiny House on the River

Lakefront Boardwalk

Magazine-Worthy Farmhouse| Hot Tub| 3 Acres| Bocce

Sister Lakes A-Frame: Private Beach, Dock & Kayaks
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- Warren Dunes State Park
- University of Notre Dame
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- Saugatuck Dunes State Park
- Oval Beach
- Washington Park Zoo
- Bittersweet Ski Resort
- Silver Beach Carousel
- Potato Creek State Park
- New Buffalo Public Beach
- Gun Lake Casino
- Fenn Valley Vineyards
- South Beach
- Grand Mere State Park
- 12 Corners Vineyards
- Van Buren State Park
- Shady Creek Winery
- Weko Beach
- Jean Klock Park
- Saugatuck Dune Rides
- Silver Beach Park
- Holland State Park Lake Macatawa Campground
- Four Winds Casino
- Woodlands Course at Whittaker





