Holiday rentals in Keeler Township

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Top-rated holiday rentals in Keeler Township

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Top guest favourite
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
4.98 out of 5 average rating, 105 reviews

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

Top guest favourite
Home in Buchanan
4.97 out of 5 average rating, 127 reviews

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

Guest favourite
A two-story blue house is positioned near the water, featuring a white deck on the upper level and an inviting staircase. A yellow boat lift is visible at the water's edge, along with a small beach area and lush greenery surrounding the property.
Home in Dowagiac
4.92 out of 5 average rating, 13 reviews

Grecian Getaway

We welcome you to our lakeside home in SW Michigan, on Big Crooked Lake. Enjoy summer lake activities, winter snowmobiling or local wine tastings. Come for weddings, ND football or graduations. Walking distance to a brewery, several restaurants/bars, a coffee shop/ice cream shop & grocery store. Our home sleeps 15 people on beds & pull outs PLUS there is a crib & pack-n-play. 20 minutes east of St. Joseph & Lake Michigan, it is a 30-minute drive to South Haven, MI & 45 minutes to Notre Dame!

Top guest favourite
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
5.0 out of 5 average rating, 45 reviews

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.

Top guest favourite
Home in Coloma
5.0 out of 5 average rating, 9 reviews

Updated Cozy Cottage Near Lakes, Wineries & Trails

Deer Cottage is a warm and cozy retreat near Big & Little Paw Paw Lakes—perfect for a romantic getaway or family stay. This renovated lake home sleeps 4 with a queen bed and sleeper sofa, a fully remodeled kitchen and bath, indoor gas fireplace, and 2 smart TVs. Just a short drive away, guests can explore nearby wineries, kayak the river, or relax at Lake Michigan. Indy grandparents created this sweet escape to be near their granddaughters—complete with deer sightings right from the yard.

Top guest favourite
A welcoming patio area features a spacious wooden deck with outdoor seating for six arranged around a central fire pit. Lush greenery surrounds the space, with a variety of plants visible. The entrance to the home is framed by a white door and large sliding glass doors.
Home in Coloma
4.92 out of 5 average rating, 13 reviews

Coloma Cozy Cabin

Are you ready to experience the ultimate in coastal living? Look no further! This fully furnished 2-bedroom, 1 1/2-bath home is the perfect escape, tucked away in the heart of Coloma, Michigan. With its prime location near Pawpaw Lake, wineries, and golf courses, this home offers a unique opportunity for relaxation and adventure. This home is located 15 minutes away from St Joseph and South Haven MI. *Kal-Haven Walking/Bicycle Trail * Kayak Rentals * Four Wind Casinos * Charter Fishing

Guest favourite
The living room features two blue sofas with white accent pillows, positioned on a patterned area rug. Natural light enters through multiple windows, illuminating the space. A small side table and a decorative plant are included, along with a console table against the wall.
Home in Watervliet
4.95 out of 5 average rating, 41 reviews

Modern SW Michigan Getaway | Near Lakes & Wineries

Welcome to our new, beautifully constructed home in the heart of Watervliet, Michigan! Perfect for families and friends, this spacious retreat features 4 cozy bedrooms, 3 full baths and a loft/rec area offering ample space and entertainment for everyone. Ideally located within a 5 to 10 minute drive from: Breweries, Paw Paw Lake Golf Club, wedding venues, Four Winds Casino, Filkins Vineyards, Contessa Wine Cellars. 15-20 minutes from South Haven, Benton Harbor, Lake Michigan.

Top 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, 137 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.

Top 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.
Guest house in New Buffalo
4.96 out of 5 average rating, 689 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
Cabin in Watervliet
4.92 out of 5 average rating, 398 reviews

Riverview Cabin

Riverview Cabin is a bright riverfront studio retreat on 150 shared acres, perfect for couples or small families. Sleeps up to 4 with a king bed, futon, full kitchen, Smart TV, Wi-Fi, and a jacuzzi tub with scenic views. Relax on the private deck, gather around the fire pit, or explore 2.3 miles of riverfrontage, wooded trails, fishing ponds, and wildlife. Dog-friendly and just minutes from Lake Michigan beaches, wineries, and local attractions.

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, 437 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.

Guest favourite
Home in Dowagiac
4.93 out of 5 average rating, 90 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.

Popular amenities for Keeler Township holiday rentals