House vacation rentals in Three Oaks

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Top-rated house rentals in Three Oaks

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Superhost
A bright and airy living space reveals a cozy area featuring a light-colored ottoman and a sleek fireplace. A large indoor plant adds a touch of greenery, while a doorway leads to a well-lit bedroom area beyond. Modern furnishings are visible within the serene environment.
Home in Three Oaks
4.86 out of 5 average rating, 121 reviews

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!

Guest favorite
A comfortable living area features a dark gray sectional sofa adorned with yellow and patterned throw pillows. A light wood coffee table sits in front, with a remote control resting upon it. Natural light filters through sheer curtains, illuminating the space adorned with framed artwork.
Home in Sawyer
4.93 out of 5 average rating, 147 reviews

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.

Top guest favorite
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, 307 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.

Top guest favorite
A comfortable living space features a vintage green cabinet and a wooden dining table surrounded by black chairs. Natural light floods the room through large windows, enhancing the cozy atmosphere created by soft furnishings and decorative plants.
Home in Three Oaks
4.97 out of 5 average rating, 223 reviews

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. :)

Top guest favorite
The living room features a modern design with a mounted television above a sleek fireplace. Two comfortable armchairs flank a wooden coffee table, while natural light filters through the large windows, complemented by light-colored shades. A neutral rug adds warmth to the space.
Home in Three Oaks
4.98 out of 5 average rating, 170 reviews

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!

Guest favorite
The modern tree-house structure is illuminated by warm lighting, showcasing large windows that reflect the surrounding trees. A screened porch with seating is visible, extending from the main building, creating a connection with nature.
Home in Michigan City
4.95 out of 5 average rating, 297 reviews

TRYON FARM MID-MODERN SPA IN THE WOODS

Come, enjoy our Tryon Farm modern spa. A Sustainable luxurious open concept tree-house in the woods. Minutes from the beach with an outdoor sauna, Hottub, shower, and Mr. Steam. Perfect for two or a family/group adventure. A true destination with Yoga studio, Mirror by LuLu lemon and wellness elements. The house is a perfect balance of art and nature and luxury and spiritual. Treat yourself to a farm to table, hand made, locally sourced chef services for an extra special experience.

Guest favorite
The image displays a stylish living room featuring light-colored walls and a geometric area rug. A modern light fixture hangs above a rectangular coffee table, complemented by two leather chairs. The exterior view showcases a two-story home with a welcoming front porch and a blended color scheme.
Home in Three Oaks
4.99 out of 5 average rating, 125 reviews

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

Top guest favorite
An updated home is positioned at the center of the image, featuring a welcoming entrance with a decorative porch and large front steps. Surrounding gardens include well-maintained shrubs and trees. The sky showcases soft pink and purple hues as daylight transitions into evening.
Home in Three Oaks
5 out of 5 average rating, 104 reviews

Hot tub! In the heart of Three Oaks!

Enjoy the splendor of Michigan's Harbor Country! Our updated home is 1 block from the main street (Elm)& walkable to everything! Enjoy specialty boutiques,antiques, restaurants, bakeries, & event venues including Journeyman Distillery, Acorn (music venue) & Vickers Theater. It’s a short 10 minute drive to Lake Michigan! The friendly village of Three Oaks is the perfect place to kick back, relax, & enjoy small town living! The movie Prancer was filmed here! airbnb.com/h/7linden

Top guest favorite
A newly renovated kitchen features modern cabinetry in muted tones, with light-colored countertops and a gas range. Stainless steel appliances include a refrigerator and a coffee maker. Natural light enters through a window above the kitchen sink, creating a bright and functional space.
Home in Three Oaks
4.96 out of 5 average rating, 149 reviews

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!

Guest favorite
A modern kitchen is visible, featuring white cabinetry and stainless steel appliances. The living area includes a comfortable couch and a round table with a decorative runner. Natural light fills the space, highlighting the open layout and ceiling beams.
Home in Lakeside
4.96 out of 5 average rating, 258 reviews

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!

Top guest favorite
A charming yellow cottage is surrounded by greenery and vibrant flowers. The home features blue shutters and a welcoming front porch with white railings. A paved pathway leads to the entrance, framed by well-maintained grass and landscaping.
Home in Three Oaks
4.99 out of 5 average rating, 152 reviews

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!

Top guest favorite
A cozy sleeping area features a spacious bed with layered bedding in neutral and warm tones. A comfortable chair sits nearby, complemented by a small wooden footstool. Natural light filters through the window, illuminating the textured wall and wooden beams above.
Home in Vandalia
4.98 out of 5 average rating, 299 reviews

Hot tub, Couples, Fire Pit, Wood Supplied, Private

*Nestled on 70 acres of farm land on the banks of Christiana creek *Hot Tub…..towels provided *Perfect for two *Fully stocked kitchen *Firepit wood provided *King sized bed with plenty of bedding *Work space *Gazebo with electric *Games and puzzles *Bird feeder lots of birds *Wild life, deer, geese, ducks, coon, cranes *Cows and chickens *Star gazing *45 mins from Shipshewana, Notre Dame, and Lake Michigan *Forgot something? We got you covered

Popular amenities for Three Oaks house rentals

When is the best time to visit Three Oaks?

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Avg. priceG$42,709 GYDG$40,197 GYDG$41,872 GYDG$44,803 GYDG$47,315 GYDG$61,342 GYDG$68,460 GYDG$61,761 GYDG$53,386 GYDG$48,152 GYDG$43,965 GYDG$45,012 GYD
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Quick stats about house rentals in Three Oaks

  • Total vacation rentals

    Explore 40 vacation rentals in Three Oaks

  • Nightly prices starting at

    Three Oaks vacation rentals start at G$16,749 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Three Oaks vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Three Oaks rentals

  • 4.9 Average rating

    Three Oaks stays are highly rated by guests—averaging 4.9 out of 5!

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