Family-friendly holiday rentals in Cassopolis

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Top-rated family-friendly rentals in Cassopolis

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The exterior of a log cabin guesthouse is shown, featuring large front windows beneath a peaked roof. A vibrant patch of purple flowers and various rocks are arranged along a gravel path leading to the entrance. Lush greenery surrounds the house, enhancing its natural setting.
Guesthouse in Berrien Springs
4.83 out of 5 average rating, 379 reviews

Relax on the shores of Lake Chapin

Beautiful private self-contained Guesthouse on the shore of Lake Chapin all sports lake. Enjoy our kayaks, paddle boat & canoe. Play in the water or relax on a float just steps from the back door. New furniture & Kitchen Remodeling completed. Enjoy the fire pit or relax and watch the beautiful scenery. Enjoy the walk out deck with a wonderful view of the lake. Morning coffee with the wildlife or evening tea watching the sunset. 2022 Brand New Central A/C Installed. Pets welcome for a small fee.

Top Guest favourite
A welcoming entrance to the log home is framed by manicured grass and landscaped flower beds. The wooden porch offers a spacious area for relaxation, while the surrounding trees provide a natural, serene backdrop. Colorful flowers dot the garden, enhancing the outdoor appeal.
Guest suite in Cassopolis
4.99 out of 5 average rating, 392 reviews

The Hideaway on Mitchellii Lane

A completely furnished apartment in the basement of our log home (our main residence) on 5 acres of woods above beautiful Shavehead Lake. Entrance into the apartment through a screened in porch and double French doors provides privacy and space to relax and enjoy the beautiful outdoor landscape. A large egress window allows natural sunlight into the bedroom on the opposite side of the wall from the kitchen/dining room/living room. High speed internet & YouTubeTV provide entertainment options.

Guest favourite
Cabin in North Webster
4.89 out of 5 average rating, 261 reviews

Dock of Bay Cabin- Private Dock on Lake Webster

"Last Cast" is close to town, creating the perfect space to have access to peace & quiet while being close to town & water. This cabin is on a private property that guests will have all to themselves while they are here. You will have access to an eat in kitchen, living room, private bathroom, and a loft which has two beds. This cabin comes w/channel dock space on the S. side of Lake Webster. There is space for your boat & water toys to bring along w/ you or rent items @ a marina while here.

Top Guest favourite
A spacious living area is featured with a warm-toned sofa and two light gray chairs. Natural light floods in through multiple windows, highlighting the wooden beam ceiling. A small dining table and well-equipped kitchen are visible, creating an inviting atmosphere for relaxation.
Home in Vandalia
4.98 out of 5 average rating, 324 reviews

Romantic, Private, Retreat, Couples, Creekside,

Escape to a private Creekside retreat where peace meets connection. Perfect for couples seeking romance and comfort. This cozy getaway offers quiet moments, the soothing sounds of nature--all in a beautifully secluded setting. Relax in the hot tub under a star filled sky, enjoy a meal, book, or game while watching our feathered friends at the bird feeder right outside your door. Unwind, reconnect, and experience the simple luxury of country solitude and beauty all around you. Soul care.

Top Guest favourite
A welcoming front porch features two rocking chairs positioned beside a small decorative table, adorned with bright pink flowers. Lush greenery is visible in nearby planters, while sunlit windows with green shutters complete the charming country setting.
Guest suite in Shipshewana
4.97 out of 5 average rating, 565 reviews

Picket Fence Farm Private Guest Retreat Suite

Stay in a 2nd story private suite in a modern farmhouse where we reside on a family farm in Amish country. Guests have the entire 2nd floor: 2 bedrooms, a private bath, and a sitting room. You can watch Amish buggies drive by while you rock on the front porch, access shared patio spaces or sit by a creek. We have cows, goats & chickens. We're in the heart of Shipshewana Amish/Mennonite community, minutes from downtown Shipshewana & all it has. An authentic, comfortable country getaway.

Top Guest favourite
A cozy firepit area is surrounded by five Adirondack chairs arranged on a gravel-strewn surface. Neatly stacked firewood is visible in the background, shaded by lush greenery and trees, creating a peaceful outdoor retreat.
Bungalow in Harbert
4.97 out of 5 average rating, 219 reviews

Family Getaway with Year Round Hot Tub!

Welcome to Harbert in Harbor Country! The House on the Prairie is tucked away in a quiet location in Harbert, yet minutes from the beaches, dunes, breweries, wineries and all the Harbor Country attractions. The house features tons of amenities and is packed full of games, toys, books and activities for all ages. Enjoy the back yard amenities with a hot tub, firepit, hammock & deck! Even includes a tree house, sandpit and trampoline for the kids! Hot Tub open all year round!

Top Guest favourite
Cabin in Vandalia
4.97 out of 5 average rating, 145 reviews

Spacious Log Cabin on Beautiful Shavehead Lake

Enjoy the rustic beauty of southern Michigan in a recently completely renovated log cabin on beautiful Shavehead Lake. A two-level log cabin built into a natural hillside, this secluded property is tucked away on the south creek of the lake, and includes a dock with direct water access, canoe, 2 kayaks & life jackets included. Handicapped accessible. Easy access from the IN Toll road, 35 minutes to ND, 4 Winds Casino or Shipshewana. 1Hour to Lighthouse Outlets & IN dunes.

Guest favourite
A wooden pathway leads to a building, bordered by planters with greenery. Tall pine trees and lush grass are visible in the background, creating a natural setting. A sign featuring a horse icon is affixed to a fence post, adding a rustic touch.
Apartment in Lawrence
4.79 out of 5 average rating, 102 reviews

Horses..a private lake..what more can you want?

Welcome to Cedar Lodge! We invite you to join us on our 150 acrea horse farm in SW Michigan. We share the grounds with Cedar Lodge Summer camp and Cedar Lodge Stables whose property includes a 12 acrea entirely private lake and miles of trails. Our guest apartment sits safely back off the road and allows you as much privacy as you may wish, or the ability to join in with our staff as they go about their daily routine running a farm of 55 horses.

Top Guest favourite
Guesthouse in Cassopolis
4.97 out of 5 average rating, 183 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
The exterior of a spacious guest house is presented, featuring a red metal roof and a stone-accented entrance. A wide driveway leads up to a large garage. Lush greenery surrounds the property, and the sky displays scattered clouds.
Home in Lawton
5 out of 5 average rating, 112 reviews

Copper Ridge Inn

Copper Ridge Inn is a private guest house on Carlson Farms, a 250-acre working farm. You will love the tranquility of the private lot that the house sits on with views of the farm across the street. The house includes four bedrooms, two baths, a full kitchen, and several living spaces, including a garage bar (not temperature controlled) (the only TV in the house is located in the garage). The private back yard porch is perfect for relaxing.

Top Guest favourite
A raised treehouse structure is surrounded by tall pine trees in a woodland clearing. Two wooden Adirondack chairs are positioned on the ground, facing the entrance with green doors. A staircase leads up to the deck, providing access to the elevated space.
Treehouse in East Leroy
5 out of 5 average rating, 685 reviews

Outpost Treehouse

The lookout inspired Outpost Treehouse (not actually attached to a tree) sits in a white pine forest in the middle of a 50 acre active farm. The 15 hand crafted windows allow for great views watching out for Michigan wildlife--White tail deer, turkeys, owls, coyote have all been spotted from the elevated wrap around deck. The biggest regret that guests have noted is “we wish we would have stayed longer”!

Top Guest favourite
A cozy living area features a mix of modern and rustic decor, highlighted by large glass doors that open to scenic views. Warm wooden paneling surrounds comfortable leather seating and a coffee table, while large windows invite natural light into the space.
Guesthouse in New Buffalo
4.99 out of 5 average rating, 402 reviews

Rainbows End 🌈 Bourgeois

Escape to a pet-friendly cottage in the Midwest. Nestled amidst scenic trails, with access to the South Branch of Galien River. Relax in the whirlpool tub, explore nature, and create cherished memories. Fully equipped kitchen, washer/dryer, and inviting ambiance. 10 mins from Lake Michigan, 3 miles from Fourwinds Casino. Experience rural bliss in this delightful cottage.

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