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.

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Guest favorite
The cabin is nestled among lush trees, with soft outdoor lighting illuminating the entrance. Large windows reveal a welcoming interior glow, while a small outdoor seating area is visible nearby, blending seamlessly into the surrounding natural environment.
Cabin in Union Pier
4.95 out of 5 average rating, 361 reviews

McComb's Cabin, Union Pier, MI

Giant trees welcome you down the drive back to the cabin in the woods. The cabin, along with my house and a small cottage reside on the 2 1/2 acre property. A contemporary cabin of steel and pine with vaulted ceiling and sky lights. Open living space, inviting queen size bed, luxury rain shower, full kitchen but no stove. A wood burning fireplace- fall through end of March and outside fire pit. Public beach a 5 minute drive away. Couples check out the cabin for anniversaries & special days.

Top guest favorite
Home in Three Oaks
4.97 out of 5 average rating, 232 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. :)

Superhost
An outdoor grilling area is sheltered under a gazebo, featuring a gas grill and a blue folding table. Surrounding greenery adds a natural touch to the gravel pathway leading to the white barn-style home.
Cottage in Three Oaks
4.83 out of 5 average rating, 192 reviews

It’s Sauna & Fireplace Season | Hot Tub| Sleeps 9

Wanna Play?? You name the game & we most likely have it! Outdoor fun includes YEAR-ROUND hot tub, Pickleball & Volleyball nets, Soccer goals, Putting Green, corn hole and even cruiser bikes. Indoor fun incl. complete poker table/set & a ton of board games! If you prefer to take it easy you can relax by our indoor fireplace or the outdoor fire pit, recharge in the YEAR-ROUND indoor sauna or stroll to nearby Harbert Beach. Whatever your choice, THIS is the place to experience Harbor Country

Top 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, 129 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, 106 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, 150 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!

Top guest favorite
Two white Adirondack chairs are positioned adjacent to a circular fire pit. The ground is covered with colorful fallen leaves, and trees with yellow foliage provide a natural backdrop. The scene reflects a serene outdoor space ideal for relaxation.
Apartment in Sawyer
4.89 out of 5 average rating, 120 reviews

Morton's Retreat Cozy 1 Bedroom Apartment

Cozy comfort close to Michigan's most popular state park, breweries, wineries, antique malls and farm-to-table restaurants. Morton's Retreat has plenty of room to relax. Charcoal grill and fire pit (shared with Morton’s other retreat) for use in a spacious yard. Private entrance with keyless entry makes check-in a breeze. One other Airbnb located next door in same building. Two complimentary local beers, seltzer water and a snack are provided to help kick off your stay.

Top guest favorite
A charming cabin is nestled among tall trees, with a deck visible on one side. Surrounding areas feature mowed grass and fallen leaves, creating a tranquil rural setting. Additional structures, including a shed, can be seen in the background, adding to the serene atmosphere of the property.
Guesthouse in Sawyer
4.93 out of 5 average rating, 193 reviews

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.

Top guest favorite
A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.
Guesthouse in New Buffalo
4.97 out of 5 average rating, 644 reviews

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!

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, 153 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 modern kitchen showcases rich green cabinetry and wooden countertops. Open shelves above display glassware and dishes, while stainless steel appliances, including a dishwasher and stove, are positioned for convenience. A cozy rug lies beneath the countertop area, enhancing the rustic charm.
Farm stay in Sawyer
4.98 out of 5 average rating, 443 reviews

Your SW Michigan Modern Farmhouse Cottage Awaits

Located in Sawyer, you can bike or drive to countless beaches, breweries, wineries, distilleries, and outdoor adventures. Afterward come home to this stylish modern farmhouse cottage that looks out onto 14 acres of scenic barn, pasture. and woods. Your home away from home has a well appointed kitchen for foodies who like to cook or great local dining options for those who don't.

Top guest favorite
Guest suite in Benton Harbor
4.97 out of 5 average rating, 300 reviews

The Gingerbread House, respite in the woods.

If you are looking for a zen like place to get away for a few days, the Gingerbread House is perfect. Guests have separate and private apartment (with Smart Lock) on bottom floor of (occupied) home with private patio overlooking huge ravine. Our home is surrounded by over 20 acres of woods, yet we are only minutes from grocery, restaurants, golfing and beaches.

Popular amenities for Three Oaks vacation rentals

When is the best time to visit Three Oaks?

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Avg. price$195$185$180$182$200$247$256$250$218$199$195$193
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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 20 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 40 homes with air conditioning, over 20 homes with a bbq area, 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 $80 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!

Destinations to explore

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