Holiday houses in Plainwell

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Top-rated holiday rentals in Plainwell

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

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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, 176 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.

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Top Guest favourite
The cottage's exterior showcases a welcoming entrance with a covered porch. Flower boxes are visible under each window, and a vibrant green door adds a pop of color. The pathway is bordered by lush greenery, leading to a well-maintained lawn.
Tiny home in Plainwell
4.98 out of 5 average rating, 118 reviews

The Pineapple Cottage Close to lakes and beaches!

Please keep in mind when booking there is no smoking/vaping allowed in or near this property. No exceptions. You will be charged a smoking fee. Welcome to The Pineapple Cottage, a centrally located 1-bedroom house in Plainwell, MI. Get cozy in this one of a kind pineapple-themed tiny house. Take an early morning or evening stroll downtown to enjoy shops, bars, and restaurants. Near by winter activities: Timber Ridge Ski Resort: 14 mins Bittersweet Ski Resort: 13 mins Echo Valley: 24 mins

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Superhost
Cabin in Plainwell
4.75 out of 5 average rating, 4 reviews

Log Lodge with Hot Tub, Arcade & Movie Theater

Book your relaxing getaway in this newly renovated and redecorated Lodge and Apartment - ideal for 12 guests. Located in Plainwell, this 4 bedroom, 4.5 bath Lodge includes an over the garage apartment, perfect for your family, a boys golf trip or a weekend for the girls. From your first step into our home you will be welcomed by the warmth of a not-so-traditional-lodge. Spend hours playing your favorite arcade game, take a soak in the hot tub, or enjoy a movie on the 120" projector.

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Superhost
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, 490 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.

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Top Guest favourite
Guesthouse in Plainwell
4.97 out of 5 average rating, 34 reviews

The 1869 Carriage House

Take a break and unwind at this peaceful oasis. This historical carriage house is located halfway between Kalamazoo and Grand Rapids. It has been newly renovated with all the comforts and modern amenities anyone could want while maintaining the historical character of a Victorian home. It is walking distance from the Mill 17 venue, shopping, restaurants, and bars of downtown Plainwell. Enjoy the outdoors with a stroll on the boardwalk along the river, kayaking, or skiing.

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Top Guest favourite
A firepit surrounded by a circular stone border is set in a gravel area. Wooden chairs are arranged around the firepit, offering a cozy gathering space. A large tree provides shade, with green grass and foliage visible in the background.
Guesthouse in Otsego
4.97 out of 5 average rating, 62 reviews

Great country get away with trails

One bedroom apartment with peaceful surroundings. Situated on 18 acres with groomed walking trails and community trails nearby (Kal-Haven). Couple of lakes nearby with public access and Lake Michigan about 30 miles. Centrally located to universities (WMU, K college, KVCC), racetracks (Kalamazoo Speedway 3.9 miles, Martin track 14 miles and Gingerman 26 miles), and ski resorts (Bittersweet and TimberRidge. Plenty of parking for a trailer. Come check out Allegan Co Fair.

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Top Guest favourite
A large cabin with a rustic red exterior is set on a grassy expanse. Featuring multiple balconies and large windows, it is surrounded by trees. Flower planters adorn the decks, contributing to the natural environment.
Cabin in Plainwell
5 out of 5 average rating, 43 reviews

Deer Lodge Log Cabin with hot tub

This spacious cabin features five bedrooms, three bathrooms and 2 living rooms situated on 21 acres of picturesque land. Amenities include a hot tub, dry sauna, two fireplaces, a fire pit, and a gas grill, as well as a 36-inch Blackstone griddle. The cabin is fully stocked to meet your needs. We also provide three kayaks for your use: two single kayaks and one tandem kayak. Pine Lake is just two minutes away, along with Gun Lake and Gull Lake, all conveniently nearby.

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Top Guest favourite
The exterior of a restored dairy barn is shown, featuring a symmetrical façade with a metal roof and a cupola. Flanked by well-maintained landscaping, a wide path leads to the entrance, which includes a double door flanked by seating arrangements and potted plants.
Barn in Plainwell
4.93 out of 5 average rating, 150 reviews

The Barn House

A private country estate on 9 acres in beautiful rural Michigan featuring 5-bedrooms, 2 baths and a large kitchen/living area. This restored Dairy Barn with its original beams was converted into a wonderful residence in the early 1990’s. Cozy, tranquil, and spacious (4,000 square feet) would be a few words to best describe this home with its scenic walk out balcony overlooking a pond. The home owner currently resides in a private apartment in the lower level.

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Top Guest favourite
An open floor plan is displayed, connecting the living room and kitchen. A comfortable sectional couch faces a mounted television, and a stone fireplace adds warmth. The kitchen features a large island with seating, white cabinetry, and large windows that frame views of greenery.
Home in Shelbyville
4.97 out of 5 average rating, 273 reviews

Private Treetop Escape

Surround yourself with nature at the Treetop Escape. Unwind and relax with the upmost privacy in the hills overlooking Gun Lake. Sit down in the breakfast nook with a fresh brewed coffee and catch an evening campfire just off the patio. This property gives you the secluded getaway that you've been looking for. Very close to Bay pointe, Gun Lake Casino, State Park Beach, Bittersweet Ski Resort, Hiking Trails, Restaurants, Golf Courses, and much more!

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Superhost
An outdoor seating area features light-colored cushioned chairs arranged around a fire table. A hot tub is visible nearby, with the cottage in the background. The scene is framed by tall trees, and the lake can be seen reflecting the colors of the sunset.
Cottage in Delton
4.92 out of 5 average rating, 103 reviews

Lakefront Cottage w/view, Hot Tub, kayaks, fishing

Come experience this Charming, Cozy little Cottage overlooking Wilkinson lake! Enjoy the Lake view on the perched decks, relaxing in the Hot tub or around the campfire. Swim and soak in the sun, enjoy the Beach or the huge sand box. Explore the connected all sports Wilkinson, Cloverdale, Mud and Jones lakes all from one location! Kayaks and paddle board included, or bring your own boat! Exceptional fishing from the dock even if you’re new to it.

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Guest favourite
A shared living space features a colorful armchair and a decorative area rug. A small bar area with two stools is positioned near the kitchen. The wall displays hanging plates and a map, while the room is illuminated by a ceiling fan and natural light from the window.
Guesthouse in Plainwell
4.88 out of 5 average rating, 100 reviews

Unique and Cozy One Bedroom Boho BarnLoft

Take an escape to our unique getaway. Inside you’ll find everything you need to relax in our 600sqft (completely one of a kind) loft. The Bedroom come with a comfy queen bed and the Greatroom includes a daybed w/trundle that becomes two more twins. Look out the back patio door to watch deer grazing OR go out; with dozens of lakes nearby, (Lake Doster and Doster Country Club within a half mile) you’ll be sure to find something for everyone.

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Top Guest favourite
An expansive deck features a large dining table surrounded by high chairs, overlooking a calm lake. A flag is positioned in the center of the table, with trees reflecting soft autumn colors in the water. Bright sunlight filters through scattered clouds.
Home in Plainwell
5 out of 5 average rating, 30 reviews

Pine Lake Cottage with Views

Relax with the whole family at this peaceful lakeside retreat overlooking Pine Lake. The home features a spacious deck with stunning lake views and plenty of room to unwind, whether you’re enjoying the deck or spending time by the water. The boathouse offers kayaks, a paddleboard, and water toys for endless fun on the lake. Enjoy year-round activities, with Bittersweet Ski Resort just 14 miles away and Downtown Plainwell only 8 miles away.

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Popular amenities for Plainwell holiday rentals