Vacation rentals in Dewey Lake

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Top-rated vacation rentals in Dewey Lake

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Superhost
The exterior of a log cabin guesthouse is shown, featuring large front windows beneath a peaked roof. A vibrant patch of purple flowers and various rocks are arranged along a gravel path leading to the entrance. Lush greenery surrounds the house, enhancing its natural setting.
Guesthouse in Berrien Springs
4.83 out of 5 average rating, 378 reviews

Relax on the shores of Lake Chapin

Beautiful private self-contained Guesthouse on the shore of Lake Chapin all sports lake. Enjoy our kayaks, paddle boat & canoe. Play in the water or relax on a float just steps from the back door. New furniture & Kitchen Remodeling completed. Enjoy the fire pit or relax and watch the beautiful scenery. Enjoy the walk out deck with a wonderful view of the lake. Morning coffee with the wildlife or evening tea watching the sunset. 2022 Brand New Central A/C Installed. Pets welcome for a small fee.

Guest favourite
A cozy sleeping area features a spacious bed with a soft, textured throw blanket draped over it. An antique world map hangs above the bed, complemented by warm pendant lights. A decorative pillow adds an inviting touch to the arrangement.
Cottage in Dowagiac
4.87 out of 5 average rating, 115 reviews

Vintage Romance Finds Cozy Charm at Depot Cottage

Convenience and luxury combine in this imaginative and engaging Cottage just steps away from the Historic Train Station in this Charming All-American town. Our Vintage Travel/Train themed Cottage has family friendly features, like a children's train playroom, working model trains, stocked kitchen, and a spacious enclosed backyard for four legged babies. With romantic features like a beautiful vintage soaking tub and 100% linen bedsheets we fit any vacation requirement. Walkable to all needs.

Superhost
A living area features a dark sofa adorned with yellow and blue accent pillows. Two light-colored armchairs flank a white coffee table centered on a striped area rug. Large windows provide natural light, with views of the backyard and sliding doors leading to a deck.
Cottage in Stevensville
4.91 out of 5 average rating, 148 reviews

Escape to The Sunshine Cottage of Harbor Country!

Cozy up at The Sunshine Cottage of Harbor Country. Surrounded by award-winning beaches, state parks, wineries, and breweries this location boasts endless activities within a short walk, bike, and drive. With a large backyard and extended porch deck, the cottage offers outdoor fun and entertaining all summer long, or retreat for a cozy winter getaway. The cottage is in close proximity to Lake Michigan and Grand Mere State park - sand dunes, hiking trails, and nature adventures all seasons.

Top guest favourite
The exterior of a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.
Farm stay in Vandalia
5 out of 5 average rating, 263 reviews

Luxury Country Retreat for Romantic Escape, Creek

*Escape to your private couple’s retreat. *Whether sipping coffee at sunrise or star gazing, The Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug to reconnect

Top guest favourite
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
4.96 out of 5 average rating, 24 reviews

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!

Guest favourite
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
4.96 out of 5 average rating, 132 reviews

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.

Guest favourite
A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.
Guesthouse in New Buffalo
4.96 out of 5 average rating, 654 reviews

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Guest favourite
A charming waterfront property is showcased, featuring a spacious deck with two red umbrellas providing shade. A small red shed is visible, along with seating options, and colorful paddle boats are moored nearby. Lush green trees surround the area, complementing the serene setting.
Cottage in Dowagiac
4.94 out of 5 average rating, 16 reviews

Pontoon Included *5/1/26-10/12/26* MI Getaway

Recently updated inside & out, this 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!

Top guest favourite
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
4.99 out of 5 average rating, 400 reviews

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.

Top guest favourite
The exterior of the cottage showcases a spacious deck adorned with colorful Adirondack chairs. Large glass doors reflect the surrounding greenery, while landscaped flower beds provide a vibrant touch. A gas grill is visible near the deck, enhancing the outdoor gathering space.
Cottage in Bangor
4.95 out of 5 average rating, 232 reviews

Van Auken Lake cottage rental

This cottage ambiance is quiet and relaxing. You have the option of relaxing on the deck, kayaking on the lake, or driving a short distance to Lake Michigan. You can sit by the fire and enjoy the night sounds, or relax inside with a book or play a game together. We have quiet when you want to relax and fun towns and beaches when you are ready for exploring. It offers you a comfortable visit to a great area of Michigan.

Top guest favourite
An inviting kitchen features wooden cabinetry and granite countertops. A black 'welcome' sign is placed on the countertop next to a vase of fresh flowers. Kitchen appliances, including a coffee maker, are neatly arranged, creating a functional and welcoming space.
Guesthouse in Stevensville
4.99 out of 5 average rating, 239 reviews

The Shire

Nestled on five secluded, tree-lined acres, with a pond, waterfall, fire pit, tree swing, basketball court and walking trails, The Shire feels a million miles away from it all - but isn't! We are only minutes away from wineries, breweries, amazing beaches, restaurants and shopping. (Notre Dame is an easy 30 minute drive). Southwest Michigan is a beautiful place to live! We'd LOVE to share it with you.

Top guest favourite
Guest suite in Benton Harbor
4.97 out of 5 average rating, 307 reviews

The Gingerbread House, respite in the woods.

If you are looking for a zen like place to get away for a few days, the Gingerbread House is perfect. Guests have separate and private apartment (with Smart Lock) on bottom floor of (occupied) home with private patio overlooking huge ravine. Our home is surrounded by over 20 acres of woods, yet we are only minutes from grocery, restaurants, golfing and beaches.

Popular amenities for Dewey Lake vacation rentals