Vacation rentals in Three Oaks
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Three Oaks
Guests agree: these stays are highly rated for location, cleanliness, and more.
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. :)
Designer's Own Cozy Cottage
Kick back and unwind in this stylish getaway, ideally located in Union Pier and just a five-minute drive to New Buffalo. Tucked on the lake side of Red Arrow Highway, the Casita offers the perfect balance - close to all the action, yet a quiet retreat to call your own. Guests love visiting nearby beaches, indulging in baked goods, ice cream, local restaurants and wineries. Bike trails, hiking, pickle ball, golf and kayaking all nearby. Endless opportunities for relaxation and adventure await!
1 Block to Journeyman | Pets | Dunes & Beaches
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!
Lux, Couples Hideout, Creek, Private Hot Tub,
*Imagine soaking in your private hot tub under the stars while a gentle creek flows just steps away. You are surrounded by trees and natural beauty. *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
The Loft at the Acorn Theater
This one-of-a-kind, spacious, industrial-chic apartment is in the heart of Three Oaks historic Featherbone district. The Loft has a fully equipped kitchen, large dining table, comfy living room with a baby grand piano, and outdoor deck. Three Oaks' arts community features the acclaimed Acorn Theater, boutiques, galleries and dining options. Lake Michigan beaches, magnificent wineries, Chikaming Preserve trails, Warren Woods, and the Indiana Dunes National Park are just a short ride away.
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!
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
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!
The Sycamore Guesthouse, Across from Journeyman.
Located just steps to Journeyman Distillery! Contemporary furnishings meet within a restored Victorian home with modern conveniences. Spacious wrap-around covered porch for outdoor relaxation. Each of the five full bathrooms feature a multi-zone shower and beautiful tile work. There are a total of 5 queen beds, 2 full beds and a portable crib making room for 14 adults + children. (You can bring in additional portable cribs.) Minimum age for group rentals is 25 years of age.
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!
Sycamore Cottage - Hot Tub - Steps to Downtown 2BR
Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Sycamore Cottage. A few minutes walk to charming shops, restaurants, and event venues including Journeyman Distillery, The Acorn Theater, and The Social Club in Three Oaks. Three Oaks is just a ten minute drive from the beautiful beaches of Lake Michigan and thirty-five minutes to Notre Dame. Enjoy the small town lifestyle and find your own moment to getaway.
Rainbows End 🌈 Bourgeois
Escape to a pet-friendly cottage in the Midwest. Nestled amidst scenic trails, with access to the South Branch of Galien River. Relax in the whirlpool tub, explore nature, and create cherished memories. Fully equipped kitchen, washer/dryer, and inviting ambiance. 10 mins from Lake Michigan, 3 miles from Fourwinds Casino. Experience rural bliss in this delightful cottage.
Popular amenities for Three Oaks vacation rentals
Stay near Three Oaks's top sights
Three Oaks house rentals
Harbert Woods - 5 min walk to beach!
Charming Guesthouse with Hot tub & walk to town!
The Lucky Charm House -Walk to it all! Cute, cute
In the heart of Three Oaks! Hot tub!
The Walnut House, Michigan Woods Retreat
The treehouse at Warren Dunes
cozy new buffalo cabin, hot tub, 14m walk to beach
Pool Opens May 25! | Hot Tub • Walk to Lake
Other great vacation rentals in Three Oaks
Butternut House
Comfortable, charming vintage 2 bed/1 bth cottage
Updated Lakeside | Pool (Open!) + Hot Tub + Porch
Memorial Day Getaway or Dreamy Wedding Stay
Three Oaks Guest Nest
Verdant Hollow Farm Stay-Tigerman Black Barn
Cherry Street Guesthouse
Schoolhouse- Fenced Yard & Pet Friendly, Game Room
When is the best time to visit Three Oaks?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,321 ZAR | R3,338 ZAR | R3,187 ZAR | R3,037 ZAR | R3,338 ZAR | R4,122 ZAR | R4,272 ZAR | R4,172 ZAR | R3,638 ZAR | R3,454 ZAR | R3,204 ZAR | R3,171 ZAR |
| 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 |
Frequently Asked Questions
What are the best places to stay in Three Oaks?
Three Oaks has vacation rentals and historic inns around its town center, as well as private homes on quiet residential streets. Options often feature distinctive architecture or garden settings.
What are the best things to do in Three Oaks with kids?
Families often explore playgrounds, enjoy shows at the town theater, and join in hands-on art workshops. Local farms and markets provide additional opportunities for children to learn and play.
What are some of the best things to do in Three Oaks?
Explore independent galleries, catch a film or live show at the local historic theater, and sample regional wines in nearby tasting rooms. Outdoor markets and walking paths give a glimpse into the community’s character.
How is the weather in Three Oaks?
Three Oaks experiences cold winters with temperatures from 17-36°F (-8-2°C), and warm, humid summers between 58-83°F (15-28°C). Spring and autumn bring milder weather, with periodic rainfall throughout the year.
When is the best time to visit Three Oaks?
Late spring through early fall is often recommended for Three Oaks, when temperatures range from 48-83°F (9-28°C) and outdoor spaces are at their most vibrant. Seasonal festivals and farmers’ markets bring extra energy to the town during these months.
What are the best places to visit in Three Oaks?
You can explore local art galleries, independent shops, and the historic theater in Three Oaks. The town also has nearby nature preserves and tasting rooms that are frequently suggested by visitors.
What are some hiking trails in Three Oaks?
Three Oaks has access to local nature preserves and forested trails suited for walking and birdwatching. Wooded paths and nearby protected areas are frequently suggested for those seeking time outdoors.
What are some family activities we can do in Three Oaks?
Three Oaks has local parks for picnics and play, a historic theater with family-friendly performances, and community art workshops. Exploring farmers’ markets and nearby walking trails is also often suggested for families.
What are some of the best day trip ideas from Three Oaks?
Explore nearby Lake Michigan beaches, tour local wineries, or visit neighboring towns with additional art galleries and historic sites. Local orchards and state parks around the area also provide new sights and activities.
Are there any pet friendly accommodations available in Three Oaks?
Three Oaks has a selection of pet-friendly vacation rentals, particularly in residential neighborhoods with access to outdoor spaces. Many hosts welcome pets, so it is helpful to check individual listings for details.
What are some local tips for visiting Three Oaks?
Support local makers by exploring artisan shops, and check community boards for live music and pop-up events during your visit. Seasonal outdoor dining and tasting rooms are often recommended by residents.
What is Three Oaks known for?
Three Oaks is known for its locally rooted arts community, independent shops, and restored nineteenth-century buildings. The town has a welcoming atmosphere and regularly draws visitors for its cultural gatherings and events.
What are the best hidden gems to explore in Three Oaks?
Discover small-batch roasteries, tucked-away art spaces, and the lesser-known community gardens in Three Oaks. Occasional pop-up art installations and independently owned bookshops are often suggested by residents.
What are the best foods to try in Three Oaks?
Seasonal farm-to-table dishes, fresh baked goods, and locally produced cheeses are frequently suggested in Three Oaks. Local restaurants may also highlight Michigan craft beers and house-made desserts.
What should I bring for a trip to Three Oaks?
Bring layers for shifting weather, comfortable shoes for walking, and reusable bags for markets. Rain gear is useful in spring and autumn, and a camera is recommended for capturing local art and architecture.
What is the nightlife in Three Oaks like?
Nightlife in Three Oaks centers around cozy bars, live music venues, and occasional arts performances in intimate spaces. Locally owned establishments create a laid-back, community-focused atmosphere.
What are the most popular events or festivals in Three Oaks?
Three Oaks is known for its annual arts festivals, live music gatherings in summer, and locally organized holiday parades. Film and craft markets around major U.S. holidays are often highlighted by locals.
Are there family friendly vacation rentals in Three Oaks?
Many vacation rentals in Three Oaks are family friendly, with spacious layouts and access to shared outdoor spaces. Neighborhoods near parks or the town center are often chosen by families.
Quick stats about vacation rentals in Three Oaks
Total vacation rentals
Explore 70 vacation rentals in Three Oaks
Nightly prices starting at
Three Oaks vacation rentals start at R1,335 ZAR per night before taxes and fees
Verified guest reviews
Over 3,980 verified reviews to help you choose
Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
70 of Three Oaks vacation rentals include wi-fi access
Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Three Oaks rentals
4.9 Average rating
Three Oaks stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Chicago Vacation rentals
- Northeast Ohio Vacation rentals
- Platteville Vacation rentals
- Indianapolis Vacation rentals
- Downtown Chicago Vacation rentals
- Louisville Vacation rentals
- Detroit Vacation rentals
- Southern Indiana Vacation rentals
- Columbus Vacation rentals
- St. Louis Vacation rentals
- Cleveland Vacation rentals
- Cincinnati Vacation rentals
- Rentals with a fire pit Three Oaks
- Cabin rentals Three Oaks
- Rentals with a washer and dryer Three Oaks
- Rentals with a fireplace Three Oaks
- House rentals Three Oaks
- Pet-friendly rentals Three Oaks
- Family-friendly rentals Three Oaks
- Beachfront rentals Three Oaks
- Rentals with a patio Three Oaks
- Rentals with outdoor seating Three Oaks
- Cottage rentals Three Oaks
- Warren Dunes State Park
- University of Notre Dame
- Washington Park Zoo
- Indiana Dunes State Park
- Silver Beach Carousel
- Potato Creek State Park
- Grand Mere State Park
- Benton Harbor St Joseph Ymca
- 12 Corners Vineyards
- Beachwalk Vacation Rentals
- Woodlands Course at Whittaker
- Van Buren State Park
- Four Winds Casino
- Shady Creek Winery
- Jean Klock Park
- Weko Beach
- New Buffalo Public Beach
- Silver Beach Park
- Four Winds Casino
- Promontory Point
- Potawatomi Zoo
- South Beach
- Four Winds Field
- Dablon Winery and Vineyards