
Holiday houses in Chain-O-Lakes
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Chain-O-Lakes
Guests agree: these stays are highly rated for location, cleanliness and more.

-The District 5 Schoolhouse-
The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

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.

The Studio @ Portage Lion
Standalone 750 square foot studio on 4 beautiful acres. Renovated in 2017. Roomy and comfortable, this space is perfect for overnight to short-term stays. The space is very private, separate from the main house, has its own entrance and dedicated heating and cooling. Close to shopping and dining, 15 minutes to Notre Dame and 30 minutes from Lake Michigan beaches and resort communities. Owners live in main house on property with their very friendly dog, Poppy, 2 barn cats, and 5 free-range hens.

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.

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.

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago
Luxury meets nature: forest cabin steps from the beach, 1 hour from Chicago. Book your escape to our designer log cabin on Lake Michigan just steps from the beach and nestled in a peaceful forest, it’s the perfect retreat. Built in 1932, our charming cabin sleeps 8 in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit, games, puzzles & books. Featured in Country Living and the NYT, it’s perfect for families, friends, or retreats. Book now and create lasting memories in Michiana.

UncleLarrysLakePlace HotTubKayaksPingPong
A tribute to our favorite world traveler-he's the first to stay at our properties and give us the good, bad and ugly so we can fine-tune the ultimate experience for YOU. This newly remodeled lake home boasts 4 sleeping areas, year-round hot tub, game room with a ping pong table and large screen TV, large gathering spaces in and out, new kitchen and your own kayaks to explore the area. Enjoy sunsets and lake views from the hot tub on the expansive deck or while grilling on the Weber gas grill.

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

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.

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!

Relaxing Glamping Experience in a Tiny Cabin
Experience a serene and relaxing getaway in our tiny cabin on our farm. Created with the intention of slowing down (no tv, no wifi and no refrigerator), enjoy wandering the fields relaxing in one of the hammocks, cooking on the outdoor fire pit, sipping coffee on the front deck and generally taking a break from modern life. If you'd like to explore the area, we are nearby popular trails and bike routes, U-pick farms, breweries & restaurants and beaches along Lake Michigan.

Couples alert! PVT beach access, hot tub, firepit!
ADORABLE HOME IN LAKESIDE WAS RECENTLY REHABBED & OFFERS A SUPER CLEAN AND MODERN FEEL IN THE HEART OF HARBOR COUNTRY. GUEST HAVE ACCESS TO PRIVATE BEACH WHICH IS A 7 MIN WALK AWAY - NO CROWDED BEACHES! YEAR ROUND HOT TUB, A SUPER COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL COMPLETE THIS LOFT LIKE HOME. FULLY STOCKED KITCHEN, HIGH DEF TV, STREAM MUSIC, ETC! YOU WILL LOVE IT!
Popular amenities for Chain-O-Lakes holiday rentals
Other great holiday rentals in Chain-O-Lakes

Heated Pool | Quiet Area | Huge Fenced Yard

Verdant Hollow Farm Stay-Tigerman Black Barn

Modernized 100-year-old Home DT

Redbud Retreat | Riverfront Mid-Century Escape

Lakeside Loft Retreat

Millie's Rose Cottage

Luxury Lake Front Oasis Notre Dame Near By

Private Woodland Oasis Near Notre Dame & Lake MI
Destinations to explore
- Chicago Holiday rentals
- Northeast Ohio Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Southern Indiana Holiday rentals
- Louisville Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Cleveland Holiday rentals
- Cincinnati Holiday rentals
- Warren Dunes State Park
- University of Notre Dame
- Washington Park Zoo
- Potato Creek State Park
- Silver Beach Carousel
- Indiana Dunes State Park
- Grand Mere State Park
- 12 Corners Vineyards
- Beachwalk Vacation Rentals
- Blue Gate Restaurant & Bakery
- Woodlands Course at Whittaker
- Benton Harbor St Joseph Ymca
- Potawatomi Zoo
- Silver Beach Park
- Jean Klock Park
- Van Buren State Park
- Four Winds Casino
- New Buffalo Public Beach
- Shady Creek Winery
- Weko Beach
- Tiscornia Park
- Dablon Winery and Vineyards
- Studebaker National Museum
- Four Winds Casino




