
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.

Cabin on Swede Hill
Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Off Grid Yurt Glamping on Permaculture Homestead
Stay in our stylish yurt for a one of a kind "glamping" experience on a 20acre homestead! The perfect location on the Southwest Michigan wine trail and just 15 minutes to Lake Michigan beaches! Awesome ammenities - off grid solar power, private outhouse, outdoor shower, fans, fridge, grill, firepit, and more. Take the tour, meet sheep, horeses, chickens, rabbits and learn permaculture. Order our delicious DIY pancake breakfast featuring homemade maple syrup, our organic eggs and pancake batter.

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!

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace
Tucked away sophisticated cabin in the heart of Downtown Union Pier. Killer location that's just steps away from dining and drinks: Black Current Bakery, Neon Moon Gelato, Union Pier Market, and Union Pier Social. Townline Beach is a 10 minute walk, and the cabin is right off the bike path. Seeds Brewery is just down the road and local Wineries are 1 mile away. Back home enjoy a relaxing hot tub (available year round), wood burning fire place, spacious screened in porch & outdoor fire pit.

"Tiny House" Guest House - No Cleaning Fee
"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

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

2 BD Apt Downtown, 1 Block to Journeyman & Acorn
The Sycamore Street Apartment is a thoughtfully designed space in the heart of Three Oaks, MI. This apartment is on a quiet, tree lined street just one block from Journeyman Distillery, the Acorn Theater, and the quaint shops & restaurants lining downtown Three Oaks. Enjoy small town charm while being minutes from the beaches along Lake Michigan, Warren Dunes State Park, wineries, antiquing and all that Harbor Country has to offer. We look forward to welcoming you!

Heron's Rest Hideaway, nature lovers' dream
Privacy on 11 acres of conservancy-protected land including two small lakes, river access , woods. Rowboat available. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Kayak, bike, hike nearby. Separated from our home by a breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible. Limit of 4 guests.

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!

Poplar Place - Hot Tub - 3BR - Steps from Downtown
Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, Poplar Place. 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
Three Oaks house rentals

South Shore Studio Apartment {National Park}

Harbert Woods - 5 min walk to beach!

Darling Home + Hot Tub by Warren Dunes + Wine Bar

Dunefarmhouse Modern Country Escape

CASA TICA Serenity Amongst Nature Dog Friendly

Beautiful beach bungalow with hiking and hot tub!

The treehouse at Warren Dunes

Family Getaway with Year Round Hot Tub!
Other great vacation rentals in Three Oaks

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

6 Linden Studio

Lola's Pine Tree Cottage

Cherry Street Guesthouse

Cozy Chalet by Lake MI&Dunes with Fire Pit

4 Guest Apt Steps to Journeyman & Downtown 3 Oaks

Fascinating & Fun Family Haven w hot tub!

The Loft at the Acorn Theater
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$40,825 GYD | G$38,731 GYD | G$37,684 GYD | G$38,103 GYD | G$41,872 GYD | G$51,711 GYD | G$55,899 GYD | G$55,270 GYD | G$46,059 GYD | G$41,872 GYD | G$40,825 GYD | G$40,406 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
Do house rentals in Three Oaks have wifi?
Absolutely! We offer over 40 house rentals with wifi in Three Oaks. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Three Oaks have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Three Oaks. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Three Oaks?
Yes! Work meets play with ease at over 20 house rentals in Three Oaks featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Three Oaks have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Three Oaks. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Three Oaks?
Experience the best of Three Oaks with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly house rentals in Three Oaks?
Four-legged friends are welcome in Three Oaks. Choose from more than 10 house rentals for guests traveling with pets.
Are there family-friendly house rentals in Three Oaks?
Three Oaks has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Three Oaks?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 40 homes with air conditioning, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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$16,749 GYD per night before taxes and fees

Verified guest reviews
Over 4,290 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 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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- 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