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-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!

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. :)

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!

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus additional parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

Welcome to "Lake 2 Grapes" Bridgman is a little gem located between St. Joe and Warren Dunes. Minutes to Lake Mi. beaches, craft breweries, and wine trails. Relax in the upper level of our bi-level vacation home w/private entrance. This 3 bedroom, 2 bath includes a beautiful Master suite! Enjoy the Hot tub and fire pit in the backyard. Wine Tour? Stay with us and you'll receive a discount with "Grape & Grain Tours" plus complimentary pick up and drop off. Must be 25 or older to book.

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.

2 blocks to Journeyman, 12 mins to Beach, King Bed

Highlights: ✔ Designer rehab in 2022 ✔ Sleeps 8 ✔ Outdoor firepit ✔ Relaxing back porch ✔ 5 min walk to Journeyman ✔ Easy 5-10 min walk to Three Oaks dining + shopping ✔ 8 min to wine tastings ✔ 10 min to New Buffalo, Union Pier, Sawyer ✔ 12 min to beach ✔ Gas BBQ grill ✔ Smart TVs & board games ✔ King bed in main bedroom ✔ Fabulous front foyer for wedding photos ✔ EV charger ✔ Luxury custom-designed home ✔ 3 vehicle parking ✔ Computer workstation ✔ High speed wifi ✔ Fully stocked

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

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!

Northwind Llama retreat “Chicken coop”

Tucked away on a peaceful working llama retreat—voted the #3 stay in the state of Michigan—this charming efficiency suite offers a cozy retreat surrounded by nature. The thoughtfully designed space features ample seating for relaxing after a day outdoors with a convenient kitchenette. Step outside to not one, but two private gardens. A truly unique and tranquil getaway that blends comfort with award-winning countryside charm.