Holiday rentals 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, 80 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
The house features a distinctive curved design with large glass windows that reflect warm light, surrounded by lush gardens and greenery. The outdoor space showcases blooming flowers and well-maintained landscaping, creating a serene setting amid nature.
Home in Galesburg
5 out of 5 average rating, 173 reviews

Frank Lloyd Wright's The Meyer House

Seize this opportunity to stay in a Frank Lloyd Wright treasure! Mahogany accents have been meticulously restored, and the gardens are in full bloom throughout the season. Awarded the Seth Peterson Cottage Conservancy's 2019 Visser Award for Outstanding Restoration of a FLW House and the 2021 Wright Spirit Award in the private category. Once your reservation is confirmed you will need to provide your email in order to receive the house manual and contact information for the house manager.

Top guest favourite
Home in Fennville
4.98 out of 5 average rating, 127 reviews

Modern Home, Hot Tub, Fireplace, Game Room

Escape to this stunning modern home nestled in a beautiful wooded setting. Views of majestic trees, landscaping and daylight flooding the interior. Enjoy the indoor/outdoor fireplace. Back patio has BBQ and hot tub and roast s’mores in backyard fire pit. Well stocked kitchen has everything you need. Game Room w/pool table, ping pong, darts in attached garage. Relax and unwind at this unique vacation home minutes from Saugatuck, Lake Michigan beaches and Fenn Valley wine country. Dog friendly.

Top guest favourite
The exterior of the residence is shown, featuring a two-story blue-gray facade with white trim. Landscaping includes flowering bushes in the foreground. A street sign indicates Cedar Street and Cutler Street at the corner, emphasizing the home's location near the intersection.
Home in Allegan
4.95 out of 5 average rating, 246 reviews

The Crossroads of three highways, a cozy getaway!

The Crossroads Inn is near downtown Allegan Michigan. This wonderfully well-kept home built in the 1920s is at the busy intersections of M-89, M-40 and M-222. It is within walking distance of downtown or just minutes from any business in Allegan. Thirty minutes to South Haven and Kalamazoo. Walking distance to the Allegan County fairgrounds. If you need a central location for work in Western Michigan or a weekend getaway, the Crossroads Inn is your place to stay. Weekly and monthly discounts!

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, 281 reviews

Best Couples Vacation, Private, Hot Tub, Creek,

*Imagine soaking in your private hot tub under the stars while a gentle creek flows just steps away. You are surrounded by trees and natural beauty. *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
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, 144 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 exterior of the Eppstein House is showcased amidst autumn foliage, featuring a low-slung, geometric design. Expansive glass doors reveal warm interior lighting, contrasting beautifully with the natural stone path and surrounding trees.
Home in Galesburg
4.96 out of 5 average rating, 475 reviews

Frank Lloyd Wright’s Eppstein House

Designed by Frank Lloyd Wright, the Eppstein House is a rare architectural gem nestled in the same region as Wright’s Meyer May House in Grand Rapids, the Gilmore Car Museum in Hickory Corners, and the charming beach town of South Haven. This is a unique opportunity to experience an extraordinary home—yours to enjoy for a few unforgettable days. Travel + Leisure named the Eppstein House as Michigan’s most unique Airbnb, effectively ranking it #1 in uniqueness for the state.

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
4.96 out of 5 average rating, 56 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 rustic retreat is nestled among lush greenery, elevated on a hillside. The multi-level structure features a spacious wraparound deck, accessible by wooden stairs that cascade down the grassy slope. Sunlight filters through the surrounding trees, enhancing the natural setting.
Flat in Bloomingdale
4.85 out of 5 average rating, 86 reviews

Rustic Country Lakeside Retreat - Lower 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)!

Guest favourite
A single-story house is shown, featuring a front porch with stairs leading to the entrance. Lush green grass surrounds the home, with a large tree providing shade in the yard. A bicycle is visible near the porch, along with a garage on the side.
Home in South Haven
4.97 out of 5 average rating, 39 reviews

Woodscape at GingerMan Raceway

Going to be visiting GingerMan Raceway soon? Our place is adjacent to the track! Want to visit South Haven? Stay here and have an easy drive to all Lake Michigan has to offer. Our rental is 7 miles due East from the lake.... 10 minute drive. 1/2 mile from Kal-Haven trail. Bring your bikes or hiking shoes! Beautiful shade trees and nice breezes add for an evening of outdoor relaxation.

Top guest favourite
Cabin in Paw Paw
4.98 out of 5 average rating, 41 reviews

Cozy A-Frame Cabin With Hot Tub On Private Lake

Escape to our cozy A-frame cabin in Paw Paw, Michigan, just steps from a private neighborhood lake. Enjoy peaceful mornings with sunrise views, kayaking, and fishing a short walk away. Spend your evenings around the firepit, unwinding under the stars. Perfect for couples, friends, families or solo travelers looking for a quiet lakeside escape with a touch of adventure.

Guest favourite
The front of a rustic A-frame cabin is shown, featuring wooden siding and a welcoming door. A wooden deck extends from the entrance, surrounded by lush greenery and trees, creating a sense of harmony with the forested setting.
Place to stay in Allegan
4.93 out of 5 average rating, 112 reviews

Forest A-frame,lakeview,serenity

Nestled in a lakeside forest, this charming A-frame cabin offers serene views through large windows. Modern amenities, including a gourmet kitchen and Heat and AC, await inside. Wake up to birdsong, enjoy a spacious deck, and create unforgettable memories in nature. Your perfect escape awaits!

Popular amenities for Bloomingdale holiday rentals