House holiday rentals in Three Oaks

-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.

Walk downtown in Three Oaks Modern Victorian Home

Beautiful, large & comfortable vintage Victorian home with modern touches. Home features grand rooms, comfortable premium furnishings & vintage details throughout. Outside, you'll find a spacious fully fenced-in backyard, with plenty of room to play or relax in the sunshine, or by the firepit! Just steps (0.2 mi) to Journeyman Distillery and all that downtown Three Oaks has to offer. Central to all in Harbor Country like beaches, wineries, breweries and farm stands. Come relax in style with us!

Charming Downtown Sawyer Home Close to the Dunes

Enjoy this charming home in the heart of downtown Sawyer. Venture out on foot, and you're a 2 min walk to Greenbush, Infusco, Section House and more. Hop in the car and be at Warren Dunes or Journeyman Distillery in under 10 mins. Centrally located to be close to everything Harbor Country has to offer. Inside you'll find all the comforts of home, including a full kitchen, plush queen beds, as well as a 55" Smart TV with many apps ready to go on the Apple TV. Kitchen & bathroom basics provided.

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.

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub

Luxury farm retreat on 7 wooded acres with hot tub, yoga shed, fire pit, fully fenced yard & pond! This home is a five minute drive to the beach, blueberry picking, Burn 'Em Brewing, Shady Creek Winery, next to Tryon Farm or 10 minute drive to downtown, the casino, and the outlet mall, but our guess is that you won't want to leave the property! This designer home has super comfy beds, 800 thread count sheets, a gourmet coffee bar, screened in porch, and even a tiny library in the laundry room

1 Block to Journeyman - Dog Friendly/Patio/Firepit

Our newly built (2022) home is located just 1 block to Journeyman Distillery and the quaint downtown of 3 Oaks. Our home has been thoughtfully designed to create a serene and memorable stay for our guests. Eclectic shops, restaurants, and galleries are a short walk away. Drive to local beaches in less than 15 minutes. Spend your day exploring Harbor Country - wineries, breweries, hiking, biking, golf, beaches, blueberry picking, antiquing, and so much more. 3 Oaks is at the center of it all!

Great Yard, HOT TUB, Steps from Downtown

Welcome to the Oak St. Guest House! This 2 story single family home is just steps from local dining, including Journeyman's Distillery. Fully appointed, the home features a renovated kitchen, spacious dining room & living space. With 4 bedrooms and 2 baths, it is the perfect place for family celebrations or a home-away-from home for your entire wedding party. Featuring a vastly sized backyard, fire-pit, and grill - the Oak St. Guest House is perfect start to your summer lake vacation!

The Heartwood House<3 : DT Three Oaks w/Game Room

Newly renovated 1920's Bungalow loaded with character. Spacious interior with a mix of modern and vintage furnishings that will leave you relaxed and rested. Large private backyard with grill and firepit to enjoy starry Three Oaks nights. Only 4 blocks from Journeyman Distillery and close to all of the restaurants and shops in downtown. Perfect place to stay for a wedding or getaway near wineries, breweries and beaches. Come see the village that everyone is talking about!

cozy new buffalo cabin, hot tub, 14m walk to beach

Kick back and relax in this calm, and cozy stylish space , Brand new home . Full of windows to gaze into the forest , very private. This is the guest home behind main home . Heated polished concrete floors and a screen porch highlight the experience along with the hot tub and ultra private setting of home . 3 large bedrooms, large great room and kitchen , dinning upscale gathering area . Small train tracks next door , it runs 3-5 times a day ( usually short train ).

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!

Dog Friendly Downtown Three Oaks Cottage! Fenced!

Just a short walk to charming downtown Three Oaks, home of the famous Journeyman’s Distillery and all the shops and eateries Three Oaks has to offer. It is also a quick drive to the beautiful beaches at Warren Dunes State Park and New Buffalo. This cheerful home has queen beds and a fully stocked kitchen. Plus a huge fenced-in back yard, so bring the kids or the dogs and know they are safe while you relax in the three-season room or on the outdoor deck!