Holiday houses in Keeler Township

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Top-rated holiday rentals in Keeler Township

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Buchanan
4.97 out of 5 average rating, 108 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.

Top Guest favourite
An open living space features a combination of wood-paneled walls and ceiling with a polished hardwood floor. A spacious dining table and chairs are positioned beside a seating area, which includes a couch. A large bed is visible in the background, complemented by various window treatments.
Farm stay in Benton Harbor
4.99 out of 5 average rating, 106 reviews

Fogarty’s Flying Diamond Ranch

A unique and beautiful, newly added bunkhouse on the upper level of a barn on a working cattle ranch! Completely private and peaceful, you'll hear birds chirping and tractors running. Overlook and explore 152 acres of trails, horses, cattle and much more. Guests are encouraged to experience a tour of the ranch with Rancher Tom free of charge! 10 minutes from Silver Beach/Downtown St. Joseph and Hagar Beach, both on the gorgeous Lake Michigan. Bonfires welcome with wood provided & pet friendly!

Top Guest favourite
Cabin in Coloma
4.99 out of 5 average rating, 100 reviews

Cozy Cabin in the Woods

Just under two hours from Chicago and only 1/2 mile from Hagar Beach, this beautifully updated 100-year-old cabin offers a peaceful retreat in the woods. Surrounded by tranquil landscapes and towering trees, you’ll enjoy the perfect blend of rustic charm and modern comfort. Tucked along a quiet dirt road, the cabin is ideally located 15 minutes from South Haven and 10 minutes from St. Joseph making it close enough for dining, shopping, and activities, yet far enough to unwind in nature’s calm.

Superhost
The lodge features a spacious lakefront view with multiple decks and patio seating for outdoor relaxation. A sandy beach is visible in front, leading to calm waters. Surrounding greenery adds to the serene environment, while nearby recreational equipment hints at available activities.
Cottage in Decatur
4.85 out of 5 average rating, 95 reviews

Lakefront A-Frame - Beach, Fire Pit, SUP/Kayaks

Welcome to Keeler Lake Lodge! A year round lakefront retreat, perfect for making memories with family or friends. This 1960s a-frame sits on 100 ft of sandy beachfront on all sports Keeler Lake. It is thoughtfully updated with modern amenities while retaining it's original character. The home sleeps 10, with 3 bedrooms + a loft & 2 full baths. A grill, fire pit, kayaks, paddle boards, & lawn games make this home the perfect mix of entertainment & relaxation. Pontoon available to rent May-Oct.

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, 269 reviews

Lux, Hot Tub, Restore, Calm, Creekside, Escape

*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
The exterior of a two-story home is depicted, featuring a paved driveway that leads to a welcoming front door. Lush green landscaping surrounds the house, with neatly arranged flower beds and trees enhancing the natural setting.
Home in Coloma
4.95 out of 5 average rating, 142 reviews

Great Paw Paw Lake Getaway - Close to Beaches!

Beautiful updated home is perfect for families with upstairs and downstairs sleeping space. Upstairs has a spacious master bedroom with 1 king bed and sofa bed and a master bath. Bedroom 2 boasts 2 twin size beds as well as bedroom 3 (2 twin beds). Downstairs has a spacious kitchen & living area with 2 futon beds. Outside a spacious patio with fire pit close by. Home is close to Jollay Orchards & Contessa Wine Cellars. Beautiful St. Joseph and Silver Beach are 20 minutes away.

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!

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, 133 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
Guesthouse in Cassopolis
4.97 out of 5 average rating, 185 reviews

Cozy cottage for two with hot tub!

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

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, 408 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.

Guest favourite
A functional kitchen features a central island with a wooden countertop. White cabinetry is complemented by a black refrigerator and dark appliances. Natural light enters through a window, and a checkered mat is placed on the floor, enhancing the space's practicality.
Cottage in Dowagiac
4.83 out of 5 average rating, 77 reviews

Home Away From Home

Home across from Round Lake, in the heart of Sister Lakes. Walking distance to two breweries, multiple restaurants, roller rink, public beach, shopping and public boat launch. Plenty of room in the driveway for boat and trailer. In close proximity to many other breweries and South West Michigan Wine Trail. Located on the snowmobile trail. Perfect for all ages and all seasons get away!

Popular amenities for Keeler Township holiday rentals