
House vacation rentals in Three Oaks
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Top-rated house rentals in Three Oaks
Guests agree: these houses are highly rated for location, cleanliness, and more.

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. :)

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!

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.

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

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

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!

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!

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
House rentals with a pool

Private Cabin Retreat - Heart of Harbor Country

Just Updated in Lakeside | Pool + Hot Tub + Porch!

Beautiful RETREAT in the country

Lake House Retreat with a Pool

Beautiful, sunny 4 BR home with pool and hot tub

Fall Fun | Quiet Area | Huge Fenced Yard

Beautiful home with Beach views in Beachwalk

NB Getaway w/HotTub,Pool,BBQ & Priv Screening Room
Weekly house rentals

Duplex | Firepit | Game Room | Hot Tub-all year

Cozy cabin for two w/hot tub

Sq Toe's Last Resort:Pet-Friendly*Fenced* GameRoom

Secluded Garden New Buffalo/Lakeside MI

Four Seasons Retreat

The Walnut House, Michigan Woods Retreat

-The District 5 Schoolhouse-

Happy Acres: Modern Luxury Country Farmhouse
Private house rentals

Perfect Fall Family Getaway or Dreamy Wedding Stay

It's A Dog's Life

Schoolhouse- Fenced Yard & Pet Friendly, Game Room

Waldron Schoolhouse 30 min to Notre Dame

The Hudson 14mi to New Buffalo!

Millie's Rose Cottage

The Dune Den! Huge Yard/Firepit/Near Town+Dunes

Michigan City Indiana Dunes Beach National Park
When is the best time to visit Three Oaks?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$42,709 GYD | G$40,197 GYD | G$41,872 GYD | G$44,803 GYD | G$47,315 GYD | G$61,342 GYD | G$68,460 GYD | G$61,761 GYD | G$53,386 GYD | G$48,152 GYD | G$43,965 GYD | G$45,012 GYD |
| Avg. temp | -4°C | -3°C | 3°C | 9°C | 15°C | 20°C | 22°C | 22°C | 18°C | 11°C | 4°C | -1°C |
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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- Warren Dunes State Park
- University of Notre Dame
- Washington Park Zoo
- Silver Beach Carousel
- Potato Creek State Park
- Tippecanoe River State Park
- Deep River Waterpark
- Woodlands Course at Whittaker
- Promontory Point
- Culver Academies Golf Course
- Point O' Woods Golf & Country Club
- The Dunes Club
- Lost Dunes Golf Club
- Elcona Country Club
- South Bend Country Club
- Kennedy Water Park
- Warren Golf Course
- 12 Corners Vineyards
- Dablon Winery and Vineyards
- Shady Creek Winery