Vacation rentals in Dowagiac

5.0 out of 5 average rating, 27 reviews

A welcoming lake home is presented with a wooden deck lined with planters filled with colorful flowers. A mix of outdoor seating is arranged on the deck, and large windows allow natural light to illuminate the interior. A lush green lawn surrounds the property.

Home in Cassopolis

Cozy Diamond Lake Getaway

Relax with the whole family at this peaceful lake home conveniently located on Diamond Lake! Home features 2 bedroom and 2.5 bath that includes a soaker tub! Additional third bed available in upstairs loft for extra sleeping area. Enjoy a front and back patio for morning coffee. Seven minute walk to private association beach with lake access to Diamond Lake! Home office in case you need to catch up on a little work. Washer and dryer for convenient washing. Come enjoy a lake weekend on the lake!

FamilyLocationAmenities

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.

LocationFamilyKitchen

4.97 out of 5 average rating, 34 reviews

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!

LocationValueComfort

5.0 out of 5 average rating, 47 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

4.97 out of 5 average rating, 144 reviews

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.

LocationFamilyGetting around

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, 98 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!

FamilyLocationHospitality

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.

FamilyValueComfort

5.0 out of 5 average rating, 157 reviews

A spacious log cabin is set amidst lush greenery, complemented by a stone pathway leading to the entrance. The porch features wooden railings and is adorned with American flags. Natural light filters through the surrounding trees, enhancing the serene outdoor environment.

Cabin in Edwardsburg

The Nest - Luxurious Cabin Retreat

The Nest can accommodate a maximum of 19 guests. The Nest is a spacious sanctuary sitting on 9 acres of beautifully wooded property. This is the perfect place for your next retreat, family get together, or Notre Dame weekend. Enjoy the serenity of nature with the convenience of location. Located around 20 minutes from Notre Dame, 15 minutes from the best restaurants in the area, and 30-45 minutes from Michigan Wine Country and lakeshore.

LocationFamilyLayout

4.96 out of 5 average rating, 26 reviews

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!

LocationFamilyView

4.99 out of 5 average rating, 464 reviews

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.

ValueFamilyCheck-in

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, 51 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.

ValueFamilyHot tub

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.