Vacation rentals in Three Oaks
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Top-rated vacation rentals in Three Oaks
Guests agree: these stays are highly rated for location, cleanliness, and more.
-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.
Orange Street Getaway - Heart of Three Oaks
Charming Two-Bedroom Home in the Heart of Three Oaks This cozy two-bedroom, one-bathroom house sits in the heart of Three Oaks with a large yard and off-street parking. Enjoy a short walk downtown to unique shops, restaurants, galleries, and the historic Vickers Theatre. Three Oaks is a quaint artsy village famous for Journeyman Distillery — known for its excellent bourbon and organic spirits — and Drier’s Meat Market. Lake Michigan beaches are just minutes away. Perfect for a relaxing getaway.
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. :)
The Happy Cozy-Pets Welcome, Fire Pit, Privacy
If relaxing in nature in a calm and cozy home is what you're seeking, you'll find it here! It's been designed to make you feel at peace and comfortable inside while providing several outdoor spaces for you to enjoy the sights, sounds, and smells of nature. The open floor plan and large dining table create a grand gathering space for everybody to be together and create the memories that matter most. Feel free to safely start a campfire outside or in the fireplace indoors. It's all here for you!
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!
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
Hot tub open year round in modern/rustic cottage!
Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!
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!
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!
The Getaway - Hot Tub - 3 BR 1.5 Bath
Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Getaway. 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.
Popular amenities for Three Oaks vacation rentals
Stay near Three Oaks's top sights
Three Oaks house rentals
Three Oaks Creek House Perfect
Secluded Modern Retreat Near Beach - "Sandlot"
Quiet Nature Escape in New Buffalo
The Lucky Charm House -Walk to it all! Cute, cute
The Walnut House, Michigan Woods Retreat
Pool & Hot Tub • Walk to Lake
Debs Michigan hot tub house, open all year
Play @ The Hideaway - hot tub, sauna, gymnasium
Other great vacation rentals in Three Oaks
Butternut House
Comfortable, charming vintage 2 bed/1 bth cottage
Dreamy Wedding Stay or Perfect Group Getaway!
Downtown Three Oaks, Fire Pit, Screened Porch,
Three Oaks Guest Nest
Small Town Charm - 18 min from Notre Dame
6 Linden Studio
Verdant Hollow Farm Stay-Tigerman Black Barn
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$41,601 GYD | G$41,810 GYD | G$39,929 GYD | G$38,047 GYD | G$41,810 GYD | G$51,636 GYD | G$53,517 GYD | G$52,263 GYD | G$45,573 GYD | G$43,274 GYD | G$40,138 GYD | G$39,720 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 |
Frequently Asked Questions
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.
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.
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 G$16,724 GYD 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!
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