Vacation rentals in Dewey Lake

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Top-rated vacation rentals in Dewey Lake

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Guest favorite
Home in Dowagiac

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.

4.83 out of 5 average rating, 12 reviews
Top guest favorite
The exterior of the lake house features a multi-level design with a spacious patio area, highlighted by a fire pit surrounded by stone borders. A hot tub sits nearby, and comfortable seating is arranged under a covered balcony. Lush greenery provides a serene backdrop.
Cottage in Benton Harbor

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

4.98 out of 5 average rating, 109 reviews
Guest favorite
Home in Dowagiac

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.

4.91 out of 5 average rating, 11 reviews
Top guest favorite
A charming lakeside house is set against a backdrop of lush greenery, featuring large windows that invite natural light. A private dock extends into the water, accompanied by four kayaks neatly arranged beside it. Lounge chairs are positioned around a fire pit on the lawn.
Home in Dowagiac

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.

5.0 out of 5 average rating, 54 reviews
Superhost
Home in Dowagiac

Lorlee - A Large and Luxurious Lakefront Cottage!

This is a beautiful, large, and rather luxurious home on Dewey Lake in the Sister Lakes area of Dowagiac. It has a very fun private lakefront on Dewey Lake, with a private dock and a small private beach area. Completely gated yard, tons of outdoor furniture, and a fire ring for bonfires and s'mores! Sleeps 20 with 7 bedrooms, 13 beds, and 3.5 bathrooms! The home is dog-friendly and child-friendly and is truly a wonderful lakefront getaway for families and groups both large and small!

4.72 out of 5 average rating, 64 reviews
Top guest favorite
A lakefront home is depicted, featuring a modern two-story design with a dark roof and white siding. Soft light from string lights illuminates the outdoor space. Reflection on the calm water captures the structure and surrounding trees, creating a serene atmosphere.
Home in Dowagiac

Lakefront Boardwalk

Welcome to the Lakefront Boardwalk! Here you'll find everything to make your next visit to Sister Lakes, MI the most fun and memorable for everyone. Our home offers a completely renovated space with all the amenities needed and wanted for an amazing stay on Little Crooked Lake. Wake up to beautiful sunrises right on the water and finish the day with s'mores by the campfire. Our home is conveniently located within walking distance to the local restaurants and Driftwood Ice Cream shop.

5.0 out of 5 average rating, 33 reviews
Top guest favorite
A modern cottage exterior is presented with a sloped roof and large windows, surrounded by lush greenery. A wide pathway leads to the entrance, where sunlight filters through the trees, casting delicate shadows on the manicured lawn.
Cottage in Dowagiac

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!

4.97 out of 5 average rating, 33 reviews
Top guest favorite
A spacious cottage is surrounded by tall trees, offering shade and a relaxing environment. A large deck extends from the back, while a fire pit area with Adirondack chairs sits on the grassy lawn, inviting outdoor gatherings.
Cottage in Dowagiac

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.

4.97 out of 5 average rating, 143 reviews
Guest favorite
Cottage in Dowagiac

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!

4.96 out of 5 average rating, 25 reviews
Top guest favorite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

4.99 out of 5 average rating, 455 reviews
Guest favorite
The exterior of the Great House is showcased, featuring a two-story structure surrounded by lush greenery. A spacious deck with seating is visible in front, complemented by well-maintained landscaping. Large windows enhance the natural light, highlighting the inviting atmosphere of the property.
Home in Dowagiac

Sister Lakes - Great House + Hot Tub (Sleeps 16+!)

Located just 2 hours from Chicago and nestled in the epicenter of Sister Lakes, Michigan, Wonder Woods is a one-of-a-kind hospitality experience. Enjoy the totally updated 3,300 sq. foot Great House. The A+ location is steps from the area's most popular attractions (The Strand Brewery & Kitchen, Ramona Roller Rink & Miniature Golf, Sister Lakes Brewery, etc.) and directly across the street from the Round Lake public access.

4.96 out of 5 average rating, 49 reviews
Top guest favorite
Home in Benton Harbor

Majestic Cottage Estate with Indoor Heated Pool

Escape to this stunning 12-bed log cottage, perfect for up to 16 guests! Set on 10 private acres, it features a heated indoor pool, sauna, cold plunge, and a beautifully finished interior. Enjoy endless entertainment with a bar, arcade games, and a fun bar basement. Relax by the indoor fireplace or outdoor fire pit. Whether you're seeking adventure or relaxation, this property is the ultimate retreat! "no pets allowed"

4.97 out of 5 average rating, 34 reviews

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