Holiday houses in Bloomingdale

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Top-rated holiday rentals in Bloomingdale

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

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Top Guest favourite
The red two-story home is framed by tall trees, showcasing a contrast with the blue sky. A spacious driveway leads to an attached garage, and autumn leaves cover the ground, enhancing the serene country setting.
Farm stay in Gobles
4.95 out of 5 average rating, 84 reviews

Blueberry Country Escape

Welcome to Brookside Inn - our family blueberry farm! Brookside is a working farm located in beautiful Southwest Michigan - aka the heart of blueberry country. Our guests enjoy a quiet, country getaway. You'll be surrounded by picturesque blueberry fields on a wooded lot with covered bridge access to miles of an extensive walking trail. As an all-seasons rental, enjoy the beaches of Lake Michigan in summer, the local ski hills in the winter and of course abundant blueberry picking in the summer!

Top Guest favourite
A modern living area is featured, showcasing a comfortable sectional sofa with accent pillows and a low wooden coffee table. Natural light floods in through large sliding glass doors, revealing a view of the serene outdoor space. A fan is positioned above, enhancing airflow.
Home in Fennville
4.97 out of 5 average rating, 140 reviews

Modern Secluded Cabin, Private Hot Tub, Fire Pit

Escape to this charming cabin in the woods. Relax in total privacy and peace and quiet with majestic views of towering trees. Natural sunlight floods into the home creating a healthy environment to unwind in. Stay warm and cozy with heated concrete floors and a gas fireplace. Cook in the well the stocked kitchen. Soak away your worries in the private hot tub. Roast s’mores in the backyard fire pit and grill on the huge deck. Fun awaits in the 3-season game room in barn NOT HEATED. Dog friendly.

Guest favourite
A wooden boardwalk extends through lush greenery, bordered by dense foliage and trees. Bright green leaves and underbrush frame the pathway, leading toward a tranquil destination, inviting exploration among the natural surroundings.
Cabin in Bloomingdale
4.93 out of 5 average rating, 54 reviews

tincan camp

Lots of room to roam on this 6 acre lakefront property. A beautiful 500-ft long boardwalk to the lake. You can see the lake from the house however, you have to walk to the lake through the lovely woods on the boardwalk. This property is adjacent to the wonderful Kalhaven Trail just redone in 2024. Ride your bikes all the way to South Haven. We are on mile marker 13. This cabin is located on lake 11 which is a 51 acre lake . There are two full RV hookups on the propert for rent as well.

Top Guest favourite
A wooden dock extends into a serene lake, bordered by lush greenery. A rowboat and paddle boat are visible near the dock, with kayaks stored nearby. The updated home is seen in the background, surrounded by trees, creating a peaceful lakeside atmosphere.
Home in Gobles
4.93 out of 5 average rating, 42 reviews

Sweet Lake House, Updated 5B Lake Home Beach, Ski

Welcome to our beautiful, fully updated 5 bedroom home on the gorgeous Sweet Lake in SW Michigan! The house sits on a large, secluded lot with plenty of indoor and outdoor space. You can swim, fish, ski, snowmobile, or enjoy the lake with our kayaks, paddle boards, boats, etc. The home is conveniently located about 5 min from Gobles, 10 min to Allegan, 25 min to the beautiful beaches of Lake Michigan, 35 minutes to Saugatuck. Bittersweet Ski and Timber Ridge Ski resorts are 10 min away.

Top Guest favourite
A hot tub sits alongside a wooden deck, surrounded by a neatly arranged stone pathway. Lush greenery provides a natural backdrop, while a geodesic dome structure is visible in the distance. A decorative planter filled with white flowers adds a touch of color to the scene.
Place to stay in Bangor
4.99 out of 5 average rating, 149 reviews

The Gathering Place! Studio/Hot Tub/Patio Igloo

The Gathering place is a "barndominium" studio that sleeps 4 comfortably, just 10 miles to South Haven beaches and SW Michigan wine trails. Relax in the studio and private patio with family or invite some friends and park a camper right outside! This unique space offers a full hookup for friends to join! The studio feature a king size bed with a full size mattress that slides underneath. Stay comfortable with AC, electric fireplace, WIFI, TV, gas grill, patio with firepit and hot tub!

Guest favourite
The cottage exterior is showcased with a striking red façade and white trim. Large windows allow ample natural light. A welcoming front door is reached by a stone pathway, with a small flowerbed in front and an American flag displayed to the side.
Home in Gobles
4.93 out of 5 average rating, 82 reviews

Brandywine Hideaway

Welcome to a private oasis for 2 guests, away from the hustle and bustle! Relax and enjoy our newly renovated, cozy little cottage surrounded by trees, perfect for a couple’s get-away any season of the year. Cottage is located by Brandywine Lake (we are not directly on the lake, behind is a wooded area which backs up to the lake), perfect for fishing, as we are close to the boat launch. Cottage is also only ½ mile from the Kal-Haven trail which goes from Kalamazoo to South Haven.

Top Guest favourite
An inviting hot tub is positioned outdoors, surrounded by lush greenery. A wooden privacy screen adds to the tranquility, while an outdoor shower with modern fixtures is nearby. The patio area is designed for relaxation, creating a soothing space for unwinding.
Home in South Haven
4.97 out of 5 average rating, 281 reviews

Family Friendly Private Beach Home with Hot Tub

5 min walk to Private Beach 10 min drive to Downtown South Haven 18 min drive to Downtown Saugatuck Escape to our 3BR South Haven home in an exclusive community, just a 5-min walk to a private Lake Michigan beach. Comfortably sleeps 8. Features a private hot tub, chef's kitchen, and cozy fireplace. Perfect for families, you're just a short drive from downtown South Haven & Saugatuck. Your luxurious lakeside retreat awaits! Experience South Haven With Us & Learn More Below!

Superhost
The kitchenette is equipped with a full refrigerator and microwave, accompanied by dishes and utensils. A dining table sits adjacent to the living area, which features a cozy seating arrangement. Wall art adds a pop of color to the inviting space, illuminated by soft overhead lighting.
Apartment in Bloomingdale
4.78 out of 5 average rating, 102 reviews

North Scott Lake Glam Room Apartment Lake Access

Scott Lake Resort in Bloomingdale, Mi has amazing views & is highly rated by our guests. If you are a guest, you can be as active OR tranquil as you choose. Scott Lake Resort has something for everyone! What to expect in your rental: -Full Kitchenette (Stove & Full refrigerator) - Dishes, flatware, cookware & utensils -Coffee Maker, Toaster & Microwave -Blankets, Pillows & Towels - We do not provide daily maid service. -Cable TV -WIFI -Queen size bed & 1 pullout couch.

Top Guest favourite
A modern guest house features a striking black exterior contrasted by natural wood detailing. Large windows allow ample light to filter in, while surrounding greenery and trees provide a tranquil environment. A covered porch extends from the side, adding to the outdoor living space.
Tiny home in Middlebury
5 out of 5 average rating, 45 reviews

Modern Amish Country Tiny Home w/ Outdoor Shower

Amen Corner is a sleek, brand-new modern tiny home tucked away on 2.5 private acres of a scenic former golf course. Located in the heart of Amish Country, it’s the ultimate nature-immersed escape for two. Watch neighboring horses from the back patio, explore private walking trails, or stream your favorite series by the indoor fireplace. Whether you want to disconnect in nature or enjoy high-end comforts, this guest favorite offers the perfect peaceful sanctuary.

Top Guest favourite
A two-story home features a combination of brown wood siding and a large glass-enclosed porch. The entrance is complemented by a deck and multiple windows. A manicured lawn with green shrubs surrounds the property, while a wide driveway leads to an attached garage with several doors.
Home in Grand Junction
4.97 out of 5 average rating, 58 reviews

Private lakeside home w/hot tub

Just 20 mins outside of South Haven, this home offers space and seclusion. This home features a game room, hot tub, volley ball court, electric fire place, and private lake access means you and your family can dive right into a vacation that fits everyone’s wishlist. While a vast array of your entertainment needs are met on property, there is also a wide range of adventures nearby. There's plenty of activities and nearby events no matter the time of year!

Guest favourite
A bright, two-story rustic getaway is nestled among lush greenery, featuring a spacious deck that wraps around the upper level. Stairs lead down from the deck to the grassy yard, providing access to the natural surroundings.
Apartment in Bloomingdale
4.9 out of 5 average rating, 79 reviews

Rustic Country Lakeside Retreat - Upper Unit

Make your vacation the best ever in your bright, rustic getaway on an all sports lake. Perched on a hill overlooking the lake, you can spend your days on the expansive deck sunbathing, sipping cocktails, throwing the frisbee in the lakefront's large grassy yard, or taking a dip in the lake to cool off. For dinner, enjoy your fresh caught fish and S'mores for dessert. Come enjoy our little piece of heaven! Now with heat and air (2026)!

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, 436 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.

Popular amenities for Bloomingdale holiday rentals