Vacation rentals in Dowagiac

4.91 out of 5 average rating, 11 reviews

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.

FamilyLocationComfort

Superhost

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.

4.85 out of 5 average rating, 133 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.

FamilyValueBackyard

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.

4.97 out of 5 average rating, 33 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!

FamilyValueCleanliness

5.0 out of 5 average rating, 45 reviews

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

Come see why guests rave about Bromley Farmhouse—a five-star stay ranked in the Top 1% of Airbnb homes. Escape to our storybook farmhouse on 3 private acres, where old-world charm meets beautifully appointed modern comforts. Sip coffee on the porch, wander the gardens, play bocce under the trees, and soak under the stars in the hot tub. Minutes from downtown Dowagiac and just 30 minutes from St. Joseph and South Bend. Come experience the magic of Bromley Farmhouse for yourself.

ValueFamilyIndoor spaces

A spacious living area features large windows, allowing natural light to illuminate the room. Comfortable seating is provided by a blue sectional couch, while a wooden dining table accommodates several guests. A stone fireplace adds warmth, and a large television is mounted above the mantel.

4.98 out of 5 average rating, 55 reviews

Lake front 7 bdr w/ Game Room Hot tub Sauna Gym

Expansive 4500 sqft house with 60' of lakefront that includes lakeside bar with large 14x36' deck overlooking Dewey Lake. Relax in the hot tub, gym and sauna or take your chances in the game room all equipped with your favorite air hockey, arcade, dart board and shuffle board. equipped with a 85" TV perfect for all the big games. Sleeps 20! Inquire about our private chefs, boat captains, wine tours, yoga instructor, massage therapist, boat rental and concierge services.

LocationFamilyView

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.

4.97 out of 5 average rating, 143 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.

LocationFamilyLong stay

A spacious kitchen area features a large 15-foot island surrounded by several high-backed bar stools. Grey cabinetry and stainless-steel appliances accentuate the modern design. Natural light floods in from windows, illuminating the open layout, which includes a view of the outdoor deck.

4.98 out of 5 average rating, 97 reviews

Luxury Weekends & Events at Hatch Street Manor!

Enjoy your stay at our boutique guesthouse in SW Michigan, which sits on 3 acres, is well appointed for a perfect getaway! We are located just 80 miles (2 hours) from Chicago, 35 miles to Notre Dame, 35 miles to Kalamazoo, and a short drive to all that Dowagiac, our lakes, and surrounding areas have to offer! The house is a split level, with 5 bedrooms, 2.5 baths, a chef's kitchen, tons of space indoors and out, AND MORE! Ask about our micro-weddings + events!

FamilyLocationNearby

4.77 out of 5 average rating, 30 reviews

A red wooden house is visible along the lake, featuring large windows that reflect the surrounding greenery. A spacious deck offers seating options, while a pier extends into the water. Several lounge chairs are arranged on the sandy area by the shore.

Home in Cassopolis

Peaceful Lake-Front Home - Fenced Yard/Pets OK

Located directly on Diamond Lake, this 3BR/2BA home has a fenced yard, 70' pier, and beds for 9. Located on the west side of the lake with a bluff behind it leaves the water calm even on a windy day. Great Room has 14' redwood plank cathedral ceiling; fireplace at one end, kitchen at the other. Hardwood flooring throughout. Sunporch (with new sofa and Loveseat) faces the lake, with wrap-around deck beyond that. New Split/Mini ac/heat system.

LocationValueAir conditioning

4.96 out of 5 average rating, 24 reviews

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!

LocationFamilyAmenities

5.0 out of 5 average rating, 62 reviews

A charming cabin is surrounded by tall trees and lush greenery. A screen porch is featured, with a set of colorful outdoor chairs arranged on a grassy area, inviting relaxation. Flower beds enhance the natural setting, providing a welcoming space for guests.

Cabin in Dowagiac

Knotty pine cabin at the lake.

Lakefront cabin part of my families history with Shady Shores Resort since 1926. 1930s playground sits directly behind cabin with newly built shuffle board court. 107 feet of sandy beach with pier to fish from. Fire pit. Bags game, horse shoes. Shuffleboard with outdoor lights. Plenty of room for social distancing with 5 acres of property. LGBTQ friendly.

LocationFamilyDecor

A charming home is surrounded by mature trees on a sunny day. The exterior features a welcoming front porch with white railings. Bright red Adirondack chairs are positioned on the lawn, inviting relaxation and outdoor enjoyment.

4.94 out of 5 average rating, 105 reviews

Vacation getaway. Sister Lakes

Nice home Sister Lakes. Across from Big Crooked Lake. Short walk to boat launch. Walk to Lakeview Inn. Plenty of parking. Home is newly remodeled. This home does not come with beach access unless specifically approved by owner. Private beach across the street is for residents of Woodland Beach and any access to that area must be approved by homeowner.

ValueLocationAccuracy

An expansive outdoor area features a private heated pool surrounded by a security fence. Nearby, a covered patio area is equipped with seating and a grill. Lush green landscaping complements the natural surroundings, offering a peaceful retreat.