Holiday houses in Fair Plain

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Top-rated holiday rentals in Fair Plain

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

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Top Guest favourite
A cozy living room is featured with a soft beige sofa and an armchair in navy blue. A light rug with earthy tones is placed under a white coffee table, which holds magazines. A fireplace is surrounded by decorative mirrors, enhancing the welcoming environment.
Cottage in Stevensville
4.94 out of 5 average rating, 240 reviews

Cheerful Stevensville cottage, GREAT LOCATION!

Right in the prettiest area of Stevensville, Glenlord Cottage is an ideal location for your Southwest Michigan stay. Down the road you will find Glenlord Beach Park, a beautiful Lake Michigan overlook. Around the corner, an award-winning bakery. In Stevensville with its variety of restaurants, beaches, and shops, Glenlord Cottage is also within easy reach of many SW Michigan attractions and is well placed for visits to wineries, golf courses, and downtown St. Joseph with its shops and festivals.

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Top Guest favourite
A charming green cottage is nestled among trees, surrounded by well-kept landscaping and flower pots. A red umbrella shades a picnic table nearby, creating a welcoming outdoor space. The gravel path leads to the cottage entrance, framed by large windows for natural light.
Guesthouse in Benton Harbor
4.94 out of 5 average rating, 211 reviews

Cozy Green Cottage with Private Beach

Cozy cottage hidden away in a quiet neighborhood 1.5 blocks from Lake Michigan, featuring a screened back porch perfect for morning coffee. Near the Benton Harbor Arts District, downtown St Joe, this cottage is surrounded by local restaurants, breweries, wineries, golf courses and shops. The beach is a year round destination, each season has its own wonders. Note: no TV, and WiFi can be spotty due to hills. Expect 90+ tiered steps to the sandy beach below. AC upstairs, original claw footed tub.

ValueFamilyCleanliness

Top Guest favourite
The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.
Home in St. Joseph
5.0 out of 5 average rating, 116 reviews

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

ValueLocationSleep quality

Superhost
A cozy corner features a light wood daybed with soft, patterned pillows, complemented by an elegant rattan chair adorned with a decorative cushion. The softly lit space showcases charming archways and textured ceiling, creating an inviting atmosphere for relaxation.
Home in Benton Harbor
4.76 out of 5 average rating, 51 reviews

The 1888 House-Beach Town Luxury

The 1888 House is a delightful, unexpected gem. Once the parsonage for the former church next door it holds many stories of hospitality and refuge. Lovingly restored it to carry the same mission. The beautifully unique & natural aesthetic mixed with subtle luxury is sure to draw you home in whatever your daily adventures. Beaches, wineries, shopping, restaurants, and all pure Michigan has to offer just minutes away. Enclosed back yard/paw motel room welcomes your fur babies too. See you soon!

ValueFamilyCleanliness

Guest favourite
A light-filled living area features a black leather sofa with decorative pillows and a wooden coffee table. Natural light enters through large sliding glass doors that open to a balcony, offering views of the outdoors. A circular woven pouf adds textural contrast to the floor.
Apartment in St. Joseph
4.96 out of 5 average rating, 159 reviews

Luxury Waterfront Condo

A gorgeous top-floor 1200 sq ft condo is located in downtown Saint Joseph with a view of the Saint Joseph River. The condo is beautifully decorated and furnished with comfortable beds and spa-quality linens and toiletries. Both bedrooms have black-out curtains and flat-screen smart TVs loaded with Netflix. The open concept kitchen is supplied with everything you need to prepare a meal. The building has an elevator and dedicated underground parking. The roof has Instaworthy views. Free WIFI.

LocationFamilyCondition

Top Guest favourite
Home in Benton Harbor
5.0 out of 5 average rating, 37 reviews

Sun Sand and Tee Times

Located in the SW Michigan beach community of Harbor Shores, this property overlooks the 6th hole of the award winning Harbor Shores Golf Club, a Jack Nicklaus design. Just minutes from Jean Klock Beach & the iconic North Pier Lighthouse at Tiscornia Park. Miles of scenic walking and biking paths begin right outside your front door. Not to mention kayaking and paddleboarding on the Paw Paw river. This 4 bdr home is perfect for those who love the outdoors and want the comforts of home.

FamilyLocationWalkability

Superhost
Home in Benton Harbor
4.93 out of 5 average rating, 61 reviews

Cozy Lake MI Getaway• Fire Pit• Patio

✨ Relaxing Lake Michigan getaway just minutes from beautiful beaches and downtown St. Joseph. Spend sunny days swimming, golfing, or exploring local shops and wineries. In the evening, unwind in the backyard with the grill, patio string lights, and fire pit. Inside, enjoy plenty of space for families or groups to relax, watch movies on Roku TVs, and recharge in comfortable & cozy bedrooms. A perfect home base for beach trips, weekend escapes, and making memories with friends and family!

LocationValueKitchen

Superhost
Home in Benton Harbor
4.84 out of 5 average rating, 103 reviews

Serenity House on the River

Serenity House is an adult only retreat as it is on the bluff and no child safety equipment in place. This is A place to be serene". Escape the hustle & bustle of the city to this gorgeous, mid century modern, retreat on the river. Built in the 1950s, this midcentury modern beauty boasts 3300SQ ft, fireplace, pool table, four season room, outdoor hot tub overlooking the river, fire-pit and the property is just minutes away from the beach, downtown, restaurants, & other attractions.

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Top Guest favourite
A spacious living area features a green sectional sofa and a light-colored coffee table, surrounded by natural light from large windows. An armchair sits next to a small side table, while decorative plants and framed artwork accent the walls, contributing to a cozy environment.
Home in Benton Harbor
4.98 out of 5 average rating, 43 reviews

May Cottage near Lake Michigan

May Cottage is a cozy home in a quiet Michigan neighborhood. The streets are filled with old trees and families walking dogs. There is a full kitchen for making delicious meals or opening your Thai takeout. A record player for great music, games, and even some classic VHS tapes. Take a bubble bath with a good book or head out. You are just a short drive away from Lake Michigan, a good hike, boutiques, local restaurants, antiques, or cozy wineries. Come stay, rest, and restore.

ValueFamilySleep quality

Top Guest favourite
A logo representing 'The Blue Barn' vacation home features a stylized illustration of a blue barn set within a circular design. The text 'THE BLUE BARN' is prominently displayed in bold letters, with 'VACATION HOME' positioned below. The design has a rustic, textured finish.
Barn in Stevensville
5.0 out of 5 average rating, 219 reviews

The Blue Barn - A cozy country getaway!

Welcome to “Blue Barn” vacation home, a country retreat located between beautiful St. Joseph beaches and several Baroda wineries. A welcoming, open floor plan makes it easy for your group to spend time together. Enjoy the crisp white bedding, fully stocked coffee and wine bar, and private fire pit to unwind with friends and family. Grand Mere State Park, Weko Beach, and several local breweries are all just a short drive from this ideally located property.

FamilyLocationWi-Fi

Top Guest favourite
An inviting kitchen features wooden cabinetry and granite countertops. A black 'welcome' sign is placed on the countertop next to a vase of fresh flowers. Kitchen appliances, including a coffee maker, are neatly arranged, creating a functional and welcoming space.
Guesthouse in Stevensville
4.99 out of 5 average rating, 278 reviews

The Shire

Nestled on five secluded, tree-lined acres, with a pond, waterfall, fire pit, tree swing, basketball court and walking trails, The Shire feels a million miles away from it all - but isn't! We are only minutes away from wineries, breweries, amazing beaches, restaurants and shopping. (Notre Dame is an easy 30 minute drive). Southwest Michigan is a beautiful place to live! We'd LOVE to share it with you.

ValueFamilyOutdoor spaces

Top Guest favourite
A charming brown exterior of the home is framed by tall trees and bushes, creating a serene and private setting. Large windows provide a glimpse of the inviting spaces inside, while stone features at the base enhance the natural landscape.
Guest suite in Benton Harbor
4.97 out of 5 average rating, 346 reviews

The Gingerbread House, respite in the woods.

If you are looking for a zen like place to get away for a few days, the Gingerbread House is perfect. Guests have separate and private apartment (with Smart Lock) on bottom floor of (occupied) home with private patio overlooking huge ravine. Our home is surrounded by over 20 acres of woods, yet we are only minutes from grocery, restaurants, golfing and beaches.

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Popular amenities for Fair Plain holiday rentals