Holiday rentals in Rolling Prairie

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Top-rated holiday rentals in Rolling Prairie

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Top guest favourite
The exterior of a farmhouse is displayed, featuring a two-story structure with a red roof and white siding. A spacious deck with seating overlooks the manicured lawn, which is surrounded by trees. Bright red chairs are arranged on the ground, inviting relaxation.
Farm stay in Galien
4.98 out of 5 average rating, 145 reviews

FARM 10 acres, pond, Hot tub, king bed 30 min ND

Come to the farm for peace, quiet, nature walks, bird watching, and fishing in the spring-fed 3-acre pond and find a new sense of calm. All you need is to build a fire, then sit back and relax. Winter or summer, the farm offers 10 acres of space to run around with your pups or bags, frisbee, and even a bit of golf. Kayak or canoe, too! So many wineries, bike trails, and parks are close by. End your day with a relaxing, stargazing hot tub overlooking the pond. Enjoy! 10 min east of Three Oaks.

Guest favourite
The cabin is nestled among lush trees, with soft outdoor lighting illuminating the entrance. Large windows reveal a welcoming interior glow, while a small outdoor seating area is visible nearby, blending seamlessly into the surrounding natural environment.
Cabin in Union Pier
4.95 out of 5 average rating, 367 reviews

McComb's Cabin, Union Pier, MI

Giant trees welcome you down the drive back to the cabin in the woods. The cabin, along with my house and a small cottage reside on the 2 1/2 acre property. A contemporary cabin of steel and pine with vaulted ceiling and sky lights. Open living space, inviting queen size bed, luxury rain shower, full kitchen but no stove. A wood burning fireplace- fall through end of March and outside fire pit. Public beach a 5 minute drive away. Couples check out the cabin for anniversaries & special days.

Top guest favourite
A spacious living area showcases a light-colored sectional sofa adorned with plush pillows. Large windows allow natural light to fill the room, revealing wooden flooring and eye-catching artwork on the walls. A dining table is visible in the background, complemented by a minimalist plant.
Home in Michigan City
4.98 out of 5 average rating, 328 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

Guest favourite
A comfortable living room is highlighted by a spacious sectional sofa with decorative pillows. A light-finished wooden coffee table sits on a soft area rug featuring warm tones. Natural light enters through a large window, complemented by sheer curtains, while a ceiling fan adds a functional design element.
Home in La Porte
4.97 out of 5 average rating, 102 reviews

La Casita De Lago

Welcome to LaCasita De Lago! Charming lakefront home north of Laporte. Enjoy the serene lake view and sunsets from the spacious back yard and unwind by the firepit overlooking the water. Natures beauty at your door steps. LaCasita is located at a perfect half way point to all the NW Indiana attractions. House is located 35min from Notre Dame, 20min to Michigan Wineries and 20 min from the Dunes. Relax in this comfy Casita which comes with modern amenities, high speed wifi & so much more!

Guest favourite
The exterior of the cottage is surrounded by lush greenery, featuring a stone chimney and warm-toned siding. A small seating area with a lounge chair and table is positioned on the well-maintained lawn, creating a welcoming outdoor space.
Cottage in New Carlisle
4.89 out of 5 average rating, 102 reviews

Gram's cottage: Near Amazon Data Center & Notre D.

New Carlisle is the perfect retreat for relaxation and rejuvenation. The public beach is a 2-mile drive away, no direct access from the home. 2 private bedrooms & two non-private beds located in the loft provide sleeping space for groups. - 25 miles west of Notre Dame & 20 miles E of Michigan City, offering easy access to attractions & stunning Lake Michigan beaches. The Amazon Data Center (AWS) is just 12 minute drive. Gram's cottage provides the perfect blend of serenity and convenience.

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, 266 reviews

Lux, Hot Tub, Restore, Calm, Creekside, Escape

*Escape to your private couple’s retreat. *Whether sipping coffee at sunrise or star gazing, The Grain Binn is the perfect blend of rest and charm *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
The cabin exterior features a wooden facade with a sloped roof and a welcoming front porch. A bench sits on the porch, surrounded by potted flowers. Warm light from string lights enhances the inviting entryway, set against a backdrop of open grass and distant trees.
Tiny home in New Carlisle
4.99 out of 5 average rating, 194 reviews

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country

Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

Top guest favourite
A bright living area features a comfortable gray sofa adorned with decorative pillows, paired with a light brown armchair. Large windows provide views of lush greenery, while a striped rug anchors the space. A coffee table with a bowl sits at the center, enhancing the cozy atmosphere.
Home in Sawyer
5 out of 5 average rating, 145 reviews

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

Top guest favourite
A modern house is situated amidst lush greenery. A wooden walkway leads to the entrance, framed by trees and underbrush. Large windows reflect natural light, blending the structure harmoniously with its surroundings while offering a glimpse of the cozy interior.
Cabin in Michigan City
4.97 out of 5 average rating, 290 reviews

The Little House at Tryon Farm

The little house is located within a 170-acre modern farm community filled with open meadows, woods and dunes. Minutes to beach, 1 hour to Chicago. Relax and enjoy the property or head out to explore the lakeshore, wineries, and great area restaurants! Two bedrooms, 1.5 baths, a fully appointed kitchen, living area w/fireplace, and a large screened in porch. Large windows flood the house with natural light and will make you feel like you're living in the treetops. A perfect getaway!

Top guest favourite
Home in La Porte
4.98 out of 5 average rating, 226 reviews

Aunt Betty's Lakeside Abode, Hot Tub Steam Shower

Aunt Betty’s Lakeside Abode offers 3 king bedrooms, 2.5 baths, 2 twin cots, west-facing beautiful Stone Lake views, screened porch with gas fire, lakeside terrace, and year-round hot tub. Enjoy multiple gathering areas, a steam shower, ping-pong. Perfect for families, couples, or groups exploring LaPorte County, Indiana Dunes or wineries, breweries, trails surrounding Lake Michigan. Sleeps 8, or book with Uncle Larry’s Lake Place next door for larger groups and shared lakefront fun!

Top guest favourite
The exterior of the cottage is surrounded by trees, with a designated seating area featuring two blue Adirondack chairs and a wooden table. A firepit sits in the gravel yard, offering a natural gathering space among green foliage.
Cottage in Union Pier
4.97 out of 5 average rating, 151 reviews

Beach Bird Cottage- 5min walk to the lake! 3BR/1BA

Dear friends, Welcome to Beach Bird Cottage, situated on a quiet street with other vintage cottages in the heart of Union Pier. It is an easy 5-minute walk to an association beach. The cottage has many updates, including a new kitchen, bathroom, washer/dryer, outdoor shower and a wood stove. The master and second bedroom each have queen-size beds and the children's bedroom has two twin beds. Enjoy an early swim before breakfast or have an evening beach picnic under the sunset.

Guest favourite
A spacious screened-in porch is adorned with comfortable seating and decorative pillows. Large windows allow natural light to fill the area, while a decorative table at the center holds a selection of refreshments. The serene view of the surrounding landscape enhances the inviting ambiance.
Cottage in Harbert
4.97 out of 5 average rating, 173 reviews

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

Popular amenities for Rolling Prairie holiday rentals