Holiday houses in Dowagiac

A serene view of Big Twin Lake is displayed, showcasing calm waters reflecting the clear blue sky. Lush greenery frames the scene, with a grassy area leading to the water’s edge. Docks and boats are visible along the shoreline, adding to the tranquil landscape.

5.0 out of 5 average rating, 20 reviews

Cabin on Big Twin Lake

Enjoy the large lakefront with a sandy beach on Big Twin Lake in this rustic cabin. Sit by the firepit or take a trip around the lake on the kayaks located at the property. The home has stunning views of the lake. There are three rooms with 2 beds each. There is also a futon for additional sleeping arrangements. Full-size washer and dryer available. Big Twin Lake is a 62 acre all sports lake. Southwest Michigan is known for its many local breweries, wineries, farmer's markets, and lakes.

LocationFamilyIndoor spaces

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, 132 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.

ValueFamilyQuiet

A serene waterfront view presents a sandy beach area leading to Little Twin Lake, bordered by greenery and trees. Chairs are arranged in a circle on the lawn, complemented by kayaks resting nearby. A dock is visible in the distance, enhancing the outdoor setting.

5.0 out of 5 average rating, 27 reviews

Little Twin Lake Cottage

Relax with the whole family at this peaceful place to stayUpdated waterfront Lake House on All Sports Little Twin Lake with sandy beach area. Waterfront area highlights include sandy beach, pier, kayaks, paddle boards, lily pad, water toys, and option to separately rent newer pontoon (reach out for more details on pontoon rental). Walkout ranch features stunning views of lake with open concept. Living room opens to updated kitchen with white cabinets, quartz counters, and farm house sink.

FamilyLocationQuiet

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!

ValueLocationWalkability

4.97 out of 5 average rating, 75 reviews

A charming cottage is nestled among lush greenery, featuring a spacious deck with colorful chairs overlooking the well-maintained lawn. A mix of trees provides natural shade, enhancing the serene ambiance of the property. Windows are present on the cabin's side, suggesting a welcoming interior.

Cabin in Dowagiac

Rustic but chic cottage on hill at Dewey Lake

1960’s cottage is part of historic Shady Shores Resort that was in my family since 1926. It sits on 5.0 acres of beautiful property with its own 107 feet private beach, bicycles , fire pit, and 1930s playground. Shuffleboard court with outdoor lights, horseshoe pit. Close to Notre Dame and Lake Michigan. Wineries, apple orchards and Brewery close by. Please note this is a cottage with mini split air conditioner /heater in each bedroom and living room TV with vcr No wifi

LocationValueAir conditioning

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.

FamilyValueKitchen

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, 54 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.

FamilyLocationIndoor spaces

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.

4.96 out of 5 average rating, 142 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.

LocationFamilyQuiet

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, 96 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!

FamilyLocationBackyard

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.

4.96 out of 5 average rating, 48 reviews

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.

ValueFamilyWalkability

A lakefront home is showcased with a large wooden deck overlooking the water. The exterior features tall windows and a gentle slope leading to a sandy beach area. Several lounge chairs and colorful watercraft are arranged by the edge, while a dock extends into the lake.

4.9 out of 5 average rating, 39 reviews

Sandy-beach lakehouse on Big Twin · sleeps 11

Wake up to lake views, walk down to 105 feet of private sandy beach, and let the kids run. Our fully remodeled 4-bed, 2.5-bath lakehouse on Big Twin Lake is built for family weeks together — clear sandy-bottom swimming, a private dock, kayaks, a beach-side gazebo, and a wood firepit at the water’s edge for s’mores. Sleeps 11 across 7 beds. 2 hours from Chicago.

ValueLocationAccuracy

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.