Vacation Home Rentals By Owner In Three Oaks, MI

Summary:brbrWelcome to The Elm Street Retreat in beautiful Three Oaks, Michigan! Fully updated with a large backyard, you will love your time here in Harbor Country. Spacious interior, thoughtful finishes, & fresh design; The Elm Street Retreat is ready for your visit. no matter the season. Whether you are coming for a wedding or just a weekend away, we are just a short walk away from the popular Journeyman Distillery, Froehlich’s restaurant & event space, & tons of fun shopping. Only 6 miles to Lake MI.brbrbrbrThe Space:brbrThrough the front door you enter into a cozy living room with a TV & comfy sectional. The dining room features a farmhouse table that seats 8 & leads into a BRAND NEW & fully updated kitchen with quartz counter tops, a suite of stainless steel appliances & ample storage for your week away. The coffee bar is stocked & ready for you! Through the kitchen is a breakfast area & enclosed patio bar area. The main level also features a large bedroom with king bed & 2nd bedroom with en-suite half bathroom. brbr brbrThe second level features 2 bedrooms & a renovated full bathroom with charming clawfoot tub with shower kit. The third bedroom has a king bed with a large closet & the fourth bedroom has a queen bed. Our home comfortably sleeps 7 people.brbr brbrOne of our favorite parts of our home is the backyard. There is easy access to the beautiful deck from both the breakfast room & large bedroom. We love the outside space just as much as the inside with our great lawn & fenced in deck area.brbrbrbrGuest Access:brbrGuests have access to the entire house! Large driveway that can hold 4 cars. Three Oaks shops & restaurants are just down the street within walking distance!brbrbrbrThe Neighborhood:brbrThree Oaks, a Harbor Country community, is named for massive oaks that stood near a town rail crossing. Popular for weddings, events, or just weekends away, people visit Three Oaks from all over the country. Journeyman Distillery, Froehlich's bakery & event hall, antique stores galore - There is something for everyone in our sweet little town!brbrbrbrGetting Around:brbrThe driveway will fit a total of four cars. Two cars wide and two cars tandem. Three Oaks shops and restaurants is just a short walk down the street. Only a 10 minute drive to Lake Michigan and close to everything Harbor Country has to offer! Wineries, Breweries, nature trails, art studios, and more all within a 15 minute drive from the house!brbrbrbrOther Things to Note:brbrThree Oaks is a wonderful small town, please note that due to the close proximity to our neighbors we ask guests respect quiet hours 11pm-8am & keep noise to a minimum.

Elm St Retreat - 3 Min walk to Downtown Three Oaks

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$702.1

Welcome to your private getaway in the woods. This recently renovated home has all the amenities you need to make this a relaxing vacation. Take a dip in the pool, look for deer in the backyard, relax in the hot tub or just relax in comfortable Adirondack chairs as you take in the sunset.brbrBoard games, movie nights, long family meals make staying in just as fun as going out.brbrBring the whole family to this home with lots of room for fun.brbrNote : This is a pet-friendly home.brThe spacebrFeatures :brbr- 5 bedrooms. Two of the bedrooms have desks and monitors for easy WFH setupbr- Dining table that seats 8br- Breakfast area that seats 6br- Fully equipped kitchen with a coffee maker, toaster, instant pot and Ninja smoothie makerbr- Flatscreen TV with Chromecastbr- WiFibr- Large deck with a grill and seating for 8br- Hot tubbr- Firepit with seating for 8br- Large yard with a hammockbr- Washer and Dryerbr- Yoga Setbr- Board Gamesbr- Electronic Pianobr- 16 x 40 pool (deep end is 5’10”)brStart your morning by walking to Harbert Swedish Bakery for some baked goods and coffee. For a perfect beach day, take a 5 min drive to the gorgeous Warren Dunes or enjoy delicious food and beverages at Greenbush Brewing Company or Journeyman Distillery. You can also head towards New Buffalo beach and enjoy some of our favorite places like Red Arrow Roadhouse, Whistlestop Grocery, Oinks Dutch Treat, Villa Nova Pizzeria.brbrGuests have access to the entire home including the outdoor space.brbrHouse rules :brbr1. Number of persons staying at the house is limited strictly to what was indicated on the reservation. Parties, gatherings, or events are not permitted at the house or yard.brbr2. PET POLICY: Dogs must be pre-approved. We will consider one well-trained adult dog.brbrDogs' age, breed, and weight must be disclosed at time of reservation request. As we are in a wooded area, pets MUST be treated with a flea and tick preventative before arrival. Dogs are to be kept off of beds and furniture. By requesting to have a dog stay with you, you are affirming to us that your pet is well-behaved, has no history of aggression, and is completely, 100% housebroken. brbrDue to an allergy, we cannot accommodate cats. brbr3. Smoking (of any substance) is not allowed inside the house. Evidence of smoking will automatically forfeit your entire security deposit.brbr4. If you intend to go to the beach, please bring along your own beach towels. Kindly do not take towels out of the house.

Spacious, pet-friendly home with a pool and hot tub. Mins from Warren Dunes

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$397.33

Summary:brbrWelcome to Ash & Elm, your home away from home in beautiful Three Oaks, Michigan! Fully updated with a large backyard, you will love your time here in Harbor Country. Spacious interior, luxury bedding, thoughtful finishes, & fresh design; Ash & Elm is sure to have you feeling right at home. Whether you are coming for a wedding or just a weekend away, we are a short walk away from the popular Journeyman Distillery, Froehlich’s restaurant & event space, & tons of fun shopping. 6 miles to Lake Mi.brbrbrbrThe Space:brbrThrough the front door you enter into a cozy living room with huge TV & comfy sectional. Just beyond the living room is the dining area that features a farmhouse table that seats 8 & leads into the kitchen with breakfast bar, full suite of stainless steel appliances, & ample storage for your time away! The first floor office is the perfect spot to take some time to get some work done before you enjoy everything Harbor Country has to offer. First floor also features full bathroom with artisan tile & restored Three Oaks custom made barn wood accents. brbrbrbrThe second level features 3 bedrooms & a renovated full bath. Primary suite with King Bed, secondary bedroom with queen bed, & 3rd bedroom with custom built twin bunk beds. We love the outside space just as much as the inside with our wrap around porch, grill area with direct gas line, & our favorite spot is the custom bar & seating area that overlooks large fire pit & backyard.brbrbrbrGuest Access:brbrGuests will have full access to the entire house and set up for guest's use with the exception of a two locked owners closets. Backyard, grill area, and front porch are great spaces on the exterior of the house for guests to enjoy.brbrbrbrThe Neighborhood:brbrThree Oaks, a Harbor Country community, is named for the three massive oaks that stood near a town rail crossing when the village was founded. Popular for weddings, events, or just weekends away, people visit Three Oaks from all over the country. Journeyman Distillery, Froehlich's bakery & event hall, antique stores galore - There is something for everyone in our sweet little town!brbrbrbrGetting Around:brbrThe large driveway that will fit multiple cars. Downtown Three Oaks shops and restaurants are just around the corner within short walking distance. Only a 10 minute drive to Lake Michigan and close to everything Harbor Country has to offer! Wineries, Breweries, nature trails, art studios, and more all within a 15 minute drive from the house!brbrbrbrOther Things to Note:brbrThree Oaks is a wonderful small town with lots of shops and restaurants to explore! Please note that due to the close proximity to our neighbors, we ask guests respect quiet hours 10pm-7am & keep noise to a minimum.brbrbrbrInteraction with Guests:brbrSelf-Check in with a unique check-in code that will automatically be generated and provided to you.brbrbrbr Host is available via call/text/email with any questions or recommendations the guest be looking for!

Ash & Elm • Your Home Away From Home!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$301.6

Welcome to Sycamore Suite, a cozy yet spacious retreat perfectly located in the heart of charming Three Oaks, Michigan. Thoughtfully designed for comfort and ease, this inviting home features a bright and welcoming living area, a kitchen for home-cooked meals, an in-unit washer and dryer, and a peaceful outdoor space—ideal for enjoying morning coffee or unwinding after a day of exploring.brbrStep outside and you’re just minutes from downtown Three Oaks, known for its walkable streets, boutique shops, antique stores, cafés, and beloved local attractions like the Vickers Theatre and Acorn Theater. Wine and spirits lovers will appreciate being close to renowned destinations such as Journeyman Distillery, along with other nearby wineries and tasting rooms that make the area a favorite for weekend getaways.brbrOutdoor enthusiasts are perfectly situated to explore the region’s natural beauty, with scenic trails, parks, and countryside drives all around. And when it’s time for the beach, the sandy shores of Lake Michigan are just a short 10-minute drive away, offering swimming, sunsets, and classic beach days. You’re also within easy reach of popular lakeshore towns, local breweries, and seasonal events throughout southwest Michigan.brbrWhether you’re planning a relaxing escape, a wine weekend, or an active adventure near the lake, Sycamore Suite offers a comfortable home base with the best of Three Oaks and the Lake Michigan coast right at your fingertips.

Steps to Journeyman - Cozy Stay - Fast Wi-Fi - Pets OK - Near Lake Michigan

Three Oaks, Michigan, United States

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Bath

Sleeps

$571.14

HIGHLIGHTS:br✔ Designer rehab in 2022br✔ Sleeps 8br✔ Outdoor firepitbr✔ Relaxing back porchbr✔ 5 min walk to Journeymanbr✔ Easy 5-10 min walk to Three Oaks dining + shoppingbr✔ 8 min to wine tastingsbr✔ 10 min to New Buffalo, Union Pier, Sawyerbr✔ 12 min to beachbr✔ Gas BBQ grillbr✔ Smart TVs & board gamesbr✔ King bed in main bedroombr✔ Fabulous front foyer for wedding photosbr✔ EV chargerbr✔ Luxury custom-designed homebr✔ 3 vehicle parkingbr✔ Computer workstationbr✔ High speed wifibr✔ Fully stockedbrbrbrHOME DETAILS:brYou’ll quickly see why our guests fall in love with this beautifully remodeled modern home and utterly charming town. Picture yourself enjoying your morning coffee on the back porch, gathering with friends or family in your spacious living area, unwinding with a glass of wine, or stargazing by the outdoor fire pit. If it's a break from the everyday rush you're seeking, The Modern Oak offers the perfect immaculately clean chic-retreat for unwinding, escaping, and recharging.brbrThe Modern Oak amenities include:br✔ 3 bedrooms + 2.5 bathrooms (detailed below)br✔ 1 main floor King bedroom w/ en suite bathroom and closetbr✔ 2 upstairs Queen bedroomsbr✔ 1 bunk bed (2 twin beds) in upstairs hallway nookbr✔ 2 full bathrooms with showers, towels, and toiletriesbr✔ 1 first floor powder room (toilet/sink)br✔ Living room equipped with Smart TV, board games, record playerbr✔ Outdoor back and front porches built for relaxingbr✔ Grassy backyard for playing cornhole/bags (included)br✔ Fully stocked kitchen with new cabinets and appliancesbr✔ 6-seat dining table + 2 seat kitchen tablebr✔ Central heating/air conditioningbr✔ Dedicated workspace with computer desk in upstairs bedroombr✔ Full size washer and dryerbr✔ Starter supplies provided (e.g., coffee, toilet paper, shower toiletries)brbrTHINGS TO DO:br✔ Explore the town, fire up the grill, have a drink on the porch, and finish the night with a campfirebr✔ Taste whiskey and play putt putt at Journeyman Distillery (5 min walk)br✔ Pack a cooler and spend the day at the beach – several a short drive awaybr✔ Grab candy and ice cream at Sweet on Elm (6 min walk)br✔ Catch live music or a comedy show at The Acorn Theater (6 min walk)br✔ Shop the antique and unique home décor stores in Three Oaks (5-10 min walk)br✔ Rent bikes & grab a map from Three Oaks Spokes (8 min walk) and savor a slice from Patellie’s (6 min walk) after your ridebr✔ Climb Warren Dunes (13 min) and enjoy a magnificent view the lakebr✔ Play a round of golf at Whittaker Woods (13 min) or Harbor Shores (33 min)br✔ Dine on the rooftop at Stray Dog in New Buffalo (10 min)br✔ Visit the chickens and grab some super fresh produce at Granor Farm (9 min)br✔ Hire a driver and tour nearby wineries and breweries (several nearby)br✔ Stroll through Warren Woods State Park (4 min) or Galien Country River Park (17 min)br✔ Go for a wild ride on the water with Harbor Country Adventures (11 min)br✔ Try your luck at the Four Winds Casino (15 min)br✔ Experience history or catch a game at the Notre Dame University Campus (35 min)brbrOTHER THINGS TO NOTE:br1 small, well-trained dog (under 50 lbs) is welcome for a $75 pet accomodation fee. Yard is unfenced; dog must be leashed when outdoors, and guest is responsible for cleaning up pet waste. Guest must have pet approved by owner before entering the home.

Breezy Chic: Fresh Spring Vibes at The Modern Oak walkable to town!

Three Oaks, Michigan, United States

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Bath

Sleeps

$337.5

Fully remodeled, repainted and deep cleaned. All new beds, linens and furniture. One block from downtown Three Oaks, Antique Shops, Art Galleries, Restaurants and Journeyman Distillery. Nice outdoor deck and large fenced backyard to enjoy a quiet evening. A 10 minute drive to the Beach, New Buffalo or the Casino. Close to many wineries and breweries. Also many parks, nature areas, orchards and farmers markets nearby.

In the Heart of Three Oaks - Steps to Downtown

Three Oaks, Michigan, United States

Bed

Bath

6

Sleeps

$576.51

Welcome to Schoolhouse Stay! While our name celebrates the property's heritage as a former schoolhouse, today it's transformed into the ultimate year-round vacation destination! brbrJoin us for a stay where history meets modern leisure! Our freshly remodeled 4-bedroom, 2-bath home is perfect for families, couples, and friends' getaways! Our layout allows for valued privacy for two families, or an extended family staying together. This delightful retreat features two cozy living rooms and a dedicated game room that promises endless fun. Dog-friendly too, for a pet fee of $135 for up to two dogs. brbrNestled in a serene setting, our spacious property includes a large, fenced backyard complete with plenty of outdoor games and amenities like a Level 2 EV Charger for your use during your stay. Inside, we feature bathroom floor heaters for the fall and winter, two indoor arcade games, three smart tv's, darts, giant connect four, and countless games! A wine fridge in the dining room adds more convenience and luxury to the experience. Whether you're here for a peaceful weekend or a lively gathering, you'll find yourself completely charmed and never wanting to leave!brbrLocated in the heart of Three Oaks, this cozy retreat places you in the middle of it all while still providing peaceful privacy and seclusion. Quaint shops, gourmet restaurants, and local attractions are just a stone's throw away. Our location ensures that you're at the center of the action, making every adventure just a short drive away. The fully fenced yard offers a peaceful place to unwind, sip your morning coffee, or simply breathe in the fresh Michigan air.brbrKnown for its biking and hiking opprtunities Three Oaks delivers on recreation! Hike the dunes at Warren Woods or walk the miles of pristine beach. We are a few miles from beautiful wineries, such as our favorite, Dablon. Sip a glass while looking at their gorgeous Vineyards then head back for a grill and fire pit night in our luxurious backyard! SW Michigan has more breweries than I can name, each offering different brews and food to unwind and chill. The food scene is diverse and plentiful in our neck of the woods as well! So if you don't feel like cooking in our fully stocked kitchen (including Trader Joe's spices!), then you will surely find a restaurant or bakery that will match your tastes!brbrWhile we’re new to VRBO we’ve been renting with over 45 5 star reviews. We've hosted many two-family vacations, as well as multi generational familes, as well as couples and girlfriends trips! We had the honor to host our first honeymoon in October, and the happy couple had the time of their lives! School House Stay is for anyone and everyone! And also well-behaved pups!! Our Bernedoodle cannot get enough of the backyard and the beach!

Schoolhouse - 4- Bedroom - King Bed, Game Room, Large Fenced Yard - Dog Friendly

Three Oaks, Michigan, United States

4

Bed

Bath

Sleeps

$328.47

Escape to our charming Cherry Street Cottage, perfectly located in the heart of Three Oaks, Michigan—just one block from Elm St. which is the main street for this quaint town. brbrThis cozy and thoughtfully appointed unit offers the ideal blend of comfort, convenience, and small-town charm. Inside, you’ll find a comfortable living space to relax after a day of exploring, a kitchen for easy meals at home, an in-unit washer and dryer, and a peaceful atmosphere that makes unwinding effortless.brbrStep outside and enjoy the best of downtown Three Oaks within walking distance. Browse local shops and antique stores, grab coffee or dinner at nearby cafés and restaurants, or catch a show at the Vickers Theatre or Acorn Theater, both local favorites. Wine and spirits lovers will appreciate the close proximity to popular destinations like Journeyman Distillery and other nearby wineries and tasting rooms, all just a short drive away.brbrFor outdoor enthusiasts, the area offers scenic hiking trails, countryside views, and easy access to seasonal activities throughout southwest Michigan. When you’re ready for the water, the beautiful beaches of Lake Michigan are just a 10-minute drive away, perfect for swimming, sunset walks, and classic beach days. You’re also well-positioned to explore nearby lakeshore towns, breweries, and local events.brbrIdeal for solo travelers or up to two couples, this retreat includes high-speed internet and a dedicated workspace, making it just as suitable for remote work as it is for weekend getaways. Whether you’re here for a relaxing escape, a wine-focused weekend, or a mix of work and leisure, Cherry Street Cottage offers a welcoming home base close to everything that makes Three Oaks and the Lake Michigan coast so special.brbrYou have access to the whole unit during your stay. There is another unit connected to this property with separate entrance.

Cozy 2 bed - Steps to Journeyman - Pets OK - Fast Wi-Fi

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$1242.76

Sleeps 22 / PLAY YOUR WAY in 5891 sq ft on 22.6 acres, private oasis with pool, hot tub, sauna, gymnasium, firepit and more! 3 king size beds, 4 queen size and 2 bunk beds with trundle 1 full and two twins each. The entire group will be comfortable in this spacious and unique property.brbrThe privacy, pool, sauna, large firepit, and the gymnasium offer opportunity for games, birthday party, reception and more. This place offers something for all ages. POOL CLOSES OCT 22, 2023 for this season.brbrNEW LISTING - Wooded drive opens to your 5891 sq ft+ private oasis with pool, hot tub, sauna, gymnasium, firepit and more! Plenty of beds and space. There are 3 king size beds, 4 queen size and 2 bunk beds with trundle 1 full and two twins each. The entire group will be comfortable in this spacious and unique property.brbrThree Oaks is the art and culture center of Harbor Country with a live performance theater, fine arts cinema, art galleries, eclectic shops, and one of Michigan`s largest organic distilleries. The Village hosts the largest Flag Day celebration in the nation and the state`s largest bicycle event, the annual `Apple Cider Century`, which brings more than 5,000 cyclists to enjoy 100 miles of Harbor Country trails. Three Oaks is haven for vintage, has some of the best antique and a couple best area for hiking such as the Chikaming Preserve or Warren Woods State Park.brOnly 1hr 15 min or 75 miles from Chicago, 106 miles from Grand Rapids Michigan, 209 miles from Detroit, 169 miles from Ann Arbor. 1.8 miles to Cherry beach, 5 miles to Warren Dunes State Park beach, 4.5 miles to Warren Woods, 21 miles to Silver Beach, 35 miles to Notre Dame Stadium, 11 miles to Four Winds Casino, 21 miles to Five Pines Ministries (snow tubing), 7 miles to Silver Bullet Sport Fishing, 8 miles to New Buffalo, 7.4 miles to Bridgman, 4.3 miles from Union Pier and more.brbrFull access to home and grounds except detached garagebrbrThe Village of Three Oaks is the arts and cultural center of Harbor Country with a live performance theater, fine arts cinema, art galleries, eclectic shops, and one of Michigan`s largest organic distilleries. A stone`s throw from the shores of Lake Michigan beaches. Multiple wine tours in the greater area. A short drive from Four Winds casino.brbrGetting around is by car. Lots of activities within a 5 to 20 minute drive or take a longer road trip north to explore Michigan beach towns of St. Joe (30 minutes), South Haven or Saugatuck. Guests can bike but there is no separate bike trail; recommend experienced road bikers only.brbrWe have camaras to monitor the front yard of the house. brbrGuests will have the entire house during their stay.brbrPet fees: $50 per pet for the entire stay, no more than 3 pets. Please keep pets off furniture and no pets in courtyard. Let the owner know you are bringing pet prior to check in.brbrWashing machine has to be on normal cycle; it does not work on quick cycle.brbrThis is a house in the country. Deer, wild turkeys, and raccoons are common. Place trash in industrial bin to avoid a visit from raccoons. Sometimes a muskrat or a mouse! We do have a pest control service for mice but cannot guarantee no sightings, especially in cold weather.brNO INDOOR SMOKING. Smoking permitted outside but must dispose of butts in receptacle. brbrPets allowed (up to 3 at $50 EACH) but NO PETS in the WALLED COURTYARD / POOL area! brIf evidence of pet in walled courtyard, guest will be fined $200. brSolid waste removed from mowed yard area. brNo pets on furniture. brbrNO throwing balls or shooting anything at the gymnasium ceiling tiles. If ceiling tiles are knocked out of place, damaged or broken, it will be a $100 minimum repair fee for replacement and labor, depending on the number of tiles involved. The ceiling is 18 feet high and will not be hit or damaged from normal use of the gym and basketball court.brbrEvents need pre-approval of host. No college parties.

Play @ The Hideaway - hot tub, sauna, gymnasium

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$442.94

Enjoy your stay in this four bedroom, 2.5 bath, two story home with separate living spaces. Start your day on the balcony with a cup of coffee from our coffee/tea bar. End your day cooking on the Black Stone grill and relaxing in the game room. This home is centrally located for everything on your Harbor Country to do list. Easy walk to Art Galleries, Distillery, Restaurants, shops and Theaters. Short drive to Lake Michigan, Wineries, Breweries, and more. Great location to access bike routes.

Butternut House

Three Oaks, Michigan, United States

4

Bed

Bath

Sleeps

$334.5

Summary:brbrA charming 1890s grain house thoughtfully renewed, Berrywood Cottage is a private retreat overlooking the upper pond of Berrywood Farm. The vaulted loft bedroom, full kitchen, wood-burning fireplace, and secluded deck create a refined Harbor Country stay surrounded by orchards, trails, ponds, and open green spaces across 33 acres. The Cottage shares certain outdoor areas with guests staying in the other homes on the property. To reserve the entire estate, see our listing for Berrywood Farm.brbrbrbrThe Space:brbrThe Cottage’s main level opens with generous light and warm natural materials. A wood-burning fireplace is the focal point of the room, framed by tall windows and soft textures. Seating includes a queen pull-out sofa for additional guests, arranged for reading, quiet time, or evenings by the fire. The dining area connects to a bright galley kitchen, forming a comfortable setting for meals and time spent indoors throughout the day.brbrbrbrUpstairs, the lofted Queen bedroom feels airy and refined beneath its vaulted ceiling. Generous skylights draw in natural light and create an open, restful setting for sleep.brbrbrbrThe Cottage’s bathroom is bright and spacious, offering a full tub and shower combination, a wide vanity with dual sinks, and simple, streamlined finishes. Thoughtful lighting and understated detailing contribute to a polished feel.brbrbrbrThe property’s outdoor spaces offer a wide range of experiences. Guests may spend time exploring the wooded trails or enjoying the ponds with a canoe or fishing line. Firepits, a bocce court, and broad lawns support full days spent outside, and each season highlights a different aspect of the grounds. The historic barn contributes to the farm’s sense of place and reflects its long history.brbrbrbrBerrywood Farm sits close to Three Oaks and within easy reach of the wider Harbor Country region. Union Pier, Lakeside, New Buffalo, and Sawyer offer dining, shopping, and shoreline access, while Town Line Beach is a short drive away. Warren Dunes State Park, nearby beaches, local wineries, markets, and galleries add to the options for day trips.brbrbrbrThe Cottage at Berrywood Farm is one of 3 homes on the property. It is available as an individual rental only during May and October. Though the property does have a pool, it is closed during these months, and the outdoor areas may be shared with guests staying in the other two homes. During the summer season, Berrywood Farm is offered exclusively as a full-estate rental with all three homes reserved together. Please see our other listing for Berrywood Farm to reserve the entire farm.brbrbrbrOther Things to Note:brbrTo ensure a safe and compliant stay, all guests are required to complete identity verification prior to check-in. A valid government-issued photo ID will be collected and verified, and the name on the ID must match the credit card used for payment. When applicable, a background screening may also be required as part of the booking process.brbrbrbrAll guests are required to review and sign Juniper Holiday + Home's Guest Occupancy Agreement prior to check-in. While we understand that events can affect your trip, it is our policy to stick to the agreed-upon cancellation policy in the listing. We recommend purchasing vacation travel insurance if you suspect you may need to cancel your reservation.brbrbrbrThe minimum age to rent this property is 25.brbrbrbrPets are not allowed at this home.brbrbrbrOut of respect for our staff and their families, we do not permit check-ins or check-outs on Thanksgiving Day and Christmas Day. Thank you for your understanding.

The Cottage at Historic 33 Acre Berrywood Farm

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$322.23

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. Private Hot Tub included!

Poplar Place - 3 BR - Hot Tub - Steps from Downtown

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$294.49

Dogs Welcome w/ Fee | Modern Interior w/ Open LayoutbrbrRoad tripping through the Mitten or exploring Lake Michigan's coast Make this 3-bed, 2-bath Three Oaks vacation rental your launchpad! Offering a convenient location, a fire pit for late-night laughs, and a grill for easy dinners, this abode ensures a memorable stay for everyone. Sip your way through Harbor Country wineries or chase the sunset across quiet beaches — no matter how you spend your stay, you’ll love calling this retreat home.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 twin daybedbrbrHOME HIGHLIGHTSbr- Smart TVbr- Dining table, breakfast barbr- Wood-burning fireplacebr- Furnished deck, covered porch w/ seatingbr- Gas grillbr- Wood-burning fire pitbrbrKITCHENbr- Refrigerator, microwave, stove/oven, dishwasher, blender, toasterbr- Drip & Keurig coffee makers (coffee & sugar provided)br- Cooking basics, dishware/flatwarebr- SpicesbrbrGENERALbr- Free WiFibr- Central A/C & heatingbr- Linens & towels, trash bags & paper towelsbr- Complimentary toiletries, hair dryerbr- Washer/dryer, hangers, iron/boardbrbrFAQbr- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Single-story home, 5 steps required to enterbrbrPARKINGbr- Driveway (3 vehicles)br- Street parking prohibitedbrbr-- THE LOCATION --brbr- Walk to Journeyman Distillerybr- 6 miles to Galien River County Parkbr- 7 miles to Town Line Beachbr- 8 miles to Warren Dunes State Parkbr- 25 miles to University of Notre Damebr- 23 miles to South Bend International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 fee (+ fees & taxes, max 2 dogs)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 5 steps to enter

Steps to Elm St: Gorgeous Double-Lot Getaway

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$505.5

Summary:brbrWelcome to The Sycamore Suites, the 10 guest home just steps from Journeyman Distillery and everything that beautiful Three Oaks, Michigan has to offer! This beautifully renovated home has been thoughtfully updated with brand new kitchens & bathrooms so that you are your group can feel right at home. The property is broken up into two units (A&B) - this listing lets you utilize the entire property and access to both sides of the building with 5 total bedrooms, 3.5 bathrooms and two kitchens!brbrbrbrThe Space:brbrAs you enter the home through the Unit B door you are welcomed into a spacious dining area with a farmhouse style table that seats 5. Next to the dining table is a beautiful new kitchen with quartz countertops, beautiful blue kitchen cabinets, and brand new stainless steel appliances. Off of the dining room is a full bathroom with walk in shower and the lower level bedroom with a trundle bed. Through the double doors is a spacious living area with a large sectional, love seat, and a smart TV with streaming capabilities. Just past the living room is an enclosed back porch with an outdoor dining table that seats 6 and looks out to the back yard deck & fire-pit area. Back inside the house and in the living room you will find the spiral staircase that brings you to Unit B's two 2nd floor bedrooms. The primary bedroom has a king bed and has a full en-suite bathroom with beautiful gold fixtures and veined large format wall tiles. The second bedroom has a queen bed. brbrbrbrUnit A can be accessed by a dividing door next to the dining table in Unit B. As you enter Unit A you will be welcomed into the living space with a sofa and smart TV with streaming capabilities. Off the living room is a newly updated kitchen with quartz countertops, beautiful grey kitchen cabinets, and brand new stainless steel appliances. There is also a half bathroom located off of the living room and kitchen. Through the kitchen you will find the back door that leads to Unit A's private back porch area. The second floor of Unit A features two bedrooms; a Primary bedroom with King Bed, second bedroom with Queen bed, and a newly updated full bathroom with countertop space and large mirror perfect for getting ready for your day! Located in the 2nd floor bathroom is also a washer and dryer. brbrbrbrThe back yard features a porch that overlooks the fire pit area.brbrbrbrGuest Access:brbrThe building is split down the middle into two units Unit A & Unit B. Unit A is a 2-bedroom 1.5 Bath unit while Unit B is a 3-Bedroom 2-bath unit. This listing gives guests access to the entire property with ground floor door where guests can walk between Unit A & Unit B. brbrbrbrGuests will be sent a unique smart lock code which they can use on the front doors of the property prior to check-inbrbrbrbrThe Neighborhood:brbrThree Oaks, a Harbor Country community, is named for massive oaks that stood near a town rail crossing. Popular for weddings, events, or just weekends away, people visit Three Oaks from all over the country. Journeyman Distillery, Froehlich's bakery & event hall, antique stores galore - There is something for everyone in our sweet little town!brbrbrbrGetting Around:brbrThere is a driveway as well as a single parking space in front of the house. Three Oaks shops and restaurants is just a short walk down the street. Only a 10 minute drive to Lake Michigan and close to everything Harbor Country has to offer! Wineries, Breweries, nature trails, art studios, and more all within a 15 minute drive from the house!brbrbrbrOther Things to Note:brbrThe building is split in half with Unit A & Unit B separated on either side. This listing gives guests access to the entire property which totals 5 bedrooms and 3.5 bathrooms. To book either Unit A or Unit B which offers a smaller space, please visit those listing pages or reach out to the host.brbrbrbrInteraction with Guests:brbrHost is always available via call, text, or email to answer any questions or give area recommendations!

Sycamore Suites-Entire Home Steps from Journeyman

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$350.0

Welcome to The Oaks - a Special Place! brSTEPS AWAY from the Journeyman Distillery, Acorn Theatre and only a block away to the shops & restaurants of Three Oaks, MI - the Hallmark town of Harbor Country!brbrRenovated and professionally designed by a local interior designer, we’ve transformed this historic cottage into an incredible oasis! Enjoy this original and historic Three Oaks Cottage (former Featherbone Factory Supervisor cottage) that includes all the modern conveniences and special touches that discerning travelers expect from an exceptional rental homebrbrPerfect for wedding parties, couples, families and/or a fun friend get-away weekend, we offer hotel quality mattresses, bedding & towels; a thoughtfully stocked kitchen with a complimentary coffee & tea bar; an inviting electric fireplace, smart TVs, patio and deck with twinkle lights, gas grill, firepit & a HUMONGOUS fenced yard for kids to run safely with tons of space to play bags/horseshoes/croquet/soccer/football and more! Come relax, unwind and enjoy!brbrEach of the 3 large, comfortable bedrooms are equipped with luxurious bedding and mattresses/pillows, a luggage rack, and extra USB charging outlets per room. The two separate living/sitting areas have smart TV with Netflix. brbrThe kitchen is HUGE with dine in table/chairs, a fully equipped, modern kitchen with stainless steel appliances, (dishwasher, garbage disposal, microwave, coffee grinder, toaster, mixer, crock pot, and refrigerator with filtered ice/water) and includes a COMPLIMENTARY coffee, tea and hot chocolate bar. We have lots of wine glasses (!), spices and all the pots, pans and bakeware you need for cooking and baking. brbrThe bathroom has been updated and includes a soaking tub for two and a rain shower. We provide luxurious towels, an iron, hair dryer and other travel amenities in case you forget something. brbrWe have added for your convenience all the “extras” that make The Oaks stand out from the rest:brA new stackable washer and dryer, family board games and books, 5G wifi, central air/heat, and a humongous fenced in yard with gas grill, firepit table, twinkle lights, separate patio area, horseshoes, bags and fire pit in the yard for s’mores and cocktails to take in the SPECTACULAR sunsets we get in the backyard! brbrThe Oaks location CANNOT BE BEAT! We are within walking distance to everything Three Oaks has to offer and driving distance to all the wonderful attractions in Southwest Michigan - beaches, Warren Dunes State Park, hiking/biking trails, kayaking, wineries, breweries, dispensaries, casino, u-pick farms, shops and restaurants! brbrTHE OAKS - It’s truly a SPECIAL PLACE!brbrGuest access:brEnjoy full access to the home and our expansive fenced in yard with patio and fire-pit! The garage is a work in process and by next year, will be another inviting, indoor/outdoor space for you to enjoy!brbrSPECIAL OCCASIONS:brPlease let us know if you are coming to celebrate a special occasion - we’re happy to help with planning and reservations!brbr**We think we’ve thought of every little detail to make your stay at The Oaks relaxing, enjoyable and memorable, but in the event we’ve missed something, please let us know ASAP so we can fix it right away! brbrWe aim to make The Oaks truly an exceptional, special place you’ll return to again and again- and refer others to as well! Enjoy and Thank you!

Charming, cozy and 5 star home STEPS to Journeyman & Acorn Theatre! Large yard!

Three Oaks, Michigan, United States

Bed

1

Bath

Sleeps

$381.25

Elm St Charmer- Enjoy the detail and character of a 1910 farmhouse with high-end upgrades in this inviting 5 bed/3 bath Three Oaks home. Great for multiple families or groups coming to town for a wedding, with separate hang out spaces for adults and children. A convenient 6min walk to the downtown area, enjoy the shopping/dining/entertainment without needing to drive! Newly remodeled gourmet kitchen with quartz countertops and Viking stove, and modern air conditioning.brbrAlso close to beaches, breweries, restaurants, kayaking, wineries, antique shops, fruit farms, art galleries, and farmer's markets. Splits the distance between the best local wineries and New Buffalo, making this the perfect getaway. House comes equipped with all you'd need to for a stress free getaway, including a stocked kitchen.brbrMain floor has great open area for entertaining/family meal time- including bench seating, couch/loveseat, and large kitchen table. Main floor also includes:br- Bedroom #1: queen bedbr- Bathroom #1: full bathroom, tub/shower combobr- Additional sitting area for coffee and/cocktailsbrbrOn the second floor you will find:br- Master bedroom : queen bedbr- Master bathroom : shower/tub combobr- Bedroom #3 : Queen bedbr- Bedroom #4 : Queen bed br- Bedroom #5: bunk bed = 2 twinsbr- Bathroom #3: Third full bathroom with showerbr- Bonus room with futon and TV- great for sleeping two more people OR another hang out area

Perfect for groups! Walk to Journeyman/downtown Three Oaks

Three Oaks, Michigan, United States

5

Bed

Bath

12

Sleeps

$828.48

Summary:brbrThe Farmhouse at Berrywood Farm is a historic 4BR/4BA retreat on 33 scenic acres with bright living areas, a sunroom, a spacious deck, and community pool + firepit. Surrounded by ponds, gardens, and nature paths, it provides an inviting Harbor Country setting for families and groups. This residence shares certain outdoor areas with guests staying in the other homes on the property. To reserve the full farm, see our listing for Berrywood Farm.brbrbrbrThe Space:brbrThe Farmhouse includes 3 refined living areas suited to time together. The main great room centers on a brick fireplace and generous seating for movies or conversation. A bright sunroom offers a contemporary lounge with wide farm views, while the front sitting room provides a quiet place to read or settle in at the end of the day. The kitchen pairs historic character with beautiful updates, including butcher-block counters, classic cabinetry, and a central island for meal prep. The adjoining dining room, lined with windows overlooking the fields, brings a, inviting atmosphere for meals that naturally extend into the evening.brbrbrbrFour bright bedrooms reflect individual character, from the airy signature suite with vaulted ceilings and a built-in work area to guest rooms in soft blue and golden palettes. A cheerful bunk room with twin-over-twin bunks adds a retreat-like feel for younger guests.brbrbrbrMAIN LEVELbrbrPrimary Bedroom: King-size BedbrbrbrbrUPPER LEVELbrbrBedroom 2: Queen-size BedbrbrBedroom 3: Two Twin-size BunkbedsbrbrBedroom 4: Queen-size BedbrbrbrbrMultiple refreshed bathrooms range from light-filled spaces with double vanities and walk-in showers to vintage rooms with soaking tubs. A dedicated laundry room supports adventurous stays with modern appliances, ample counter space, and patterned wallpaper that brings a touch of charm to daily routines.brbrbrbrBerrywood Farm sits close to Three Oaks and within easy reach of the wider Harbor Country region. Union Pier, Lakeside, New Buffalo, and Sawyer offer dining, shopping, and shoreline access, while Town Line Beach is a short drive away. Warren Dunes State Park, nearby beaches, local wineries, and small-town markets contribute to a full range of day trip options.brbrbrbrThe Farmhouse at Berrywood Farm is one of 3 homes on the property. It is available as an individual rental from October through May. During the shoulder-season months of October and May, the outdoor areas may be shared with guests staying in the other two homes. The Farm’s pool opens on Memorial Day and closes during the first week of October, so it is not available with this listing. Guests have access to the outdoor areas seasonally, with the full property available during summer season only.brbrbrbrDuring the summer season, Berrywood Farm is offered exclusively as a full-estate rental with all three homes reserved together. Please see our other listing for Berrywood Farm to reserve the entire farm.brbrbrbrOther Things to Note:brbrTo ensure a safe and compliant stay, all guests are required to complete identity verification prior to check-in. A valid government-issued photo ID will be collected and verified, and the name on the ID must match the credit card used for payment. When applicable, a background screening may also be required as part of the booking process.brbrbrbrAll guests are required to review and sign Juniper Holiday + Home's Guest Occupancy Agreement prior to check-in. While we understand that events can affect your trip, it is our policy to stick to the agreed-upon cancellation policy in the listing. We recommend purchasing vacation travel insurance if you suspect you may need to cancel your reservation.brbrbrbrThe minimum age to rent this property is 25.brbrbrbrOut of respect for our staff and their families, we do not permit check-ins or check-outs on Thanksgiving Day and Christmas Day. Thank you for your understanding.

The Farmhouse at Historic 33 Acre Berrywood Farm

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$423.58

Summary:brbrLocated just steps from Journeyman Distillery, The Fourth Oak offers the perfect spot for those looking to enjoy the vibrant atmosphere of Three Oaks. With the distillery’s craft cocktails and the cozy Staymaker Restaurant just a short walk away, your days can start and end with great local drinks, food, and live music. After exploring the distillery or shopping downtown, return to your home base to unwind, grill in the backyard, or relax on the porch as the evening settles in.brbrbrbrThe Space:brbrUpon walking in the front door, the charming coziness of the spacious living room invites you into a relaxing vacation atmosphere. With lots of comfortable seating options—including some vintage antique chairs—a gas fireplace, and a flat-screen TV, it’s a popular gathering spot. But then, so is the large, deluxe kitchen island, where drinks, snacks, and good conversation can be shared day or night. The island also has a built-in stovetop for preparing scrumptious vacation meals. The fully equipped kitchen has high-end appliances and is stocked with all the essentials to help with your and your guests' cooking needs. The welcoming dining room features a table that seats 8, and it can also be used as a work-station with excellent Wi-Fi throughout the house.brbrbrbrAll of the super-comfortable rooms use top-quality bedding and linens to ensure a sound sleep and sweet dreams. Each room is stylishly decorated, with an emphasis on plush coziness. The living room has a sofa bed, so the total number of guests' sleeping options is eight.brbrbrbrMAIN FLOORbrbrBedroom 1: 1 Queen bed with ensuite bathroombrbrLiving Room: Sofa bedbrbrbrbr2ND FLOORbrbrbrbrBedroom 2: 1 Queen bedbrbrBedroom 3: Twin bunk bedsbrbrbrbrThe first-floor ensuite bathroom is highlighted by twin vanity sinks and an awesome clawfoot soaker tub-shower combo with a Rain Shower head. The upstairs full bathroom has a stylish walk-in tiled shower. There’s also a washer-dryer combo for any of your laundering needs.brbrbrbrThe huge lawn in the backyard will greet you and your guests—kids love it, too—and the gas barbecue grill can help you make mouthwatering meals to tickle your taste buds! There’s also a back porch, accessible from the kitchen, where you can chill to your heart’s content. Three quick notes to mention: the backyard is not fenced in, but this vacation rental is pet-friendly—just let us know about your 4-legged friend when you’re booking. You and your guests have full access to the house and yard, except for the basement and garage.brbrbrbrJust a stone’s throw from the gorgeous shores of Lake Michigan, the super-charming village of Three Oaks is a superb vacation destination. Downtown Three Oaks offers great restaurants, cafes, tasty bakeries, and stylish boutiques. You’ll also be able to explore nearby parks, a farmers’ market, brewpubs, the popular Journeyman Distillery, and the much-heralded Acorn Theater, a Midwestern hub for the performing arts, featuring local and regional performers and renowned national and international artists. Our guests have raved about the natural beauty of nearby Warren Woods State Park, with its lush and well-maintained hiking trails and extraordinary birdwatching opportunities. Plus, there’s Granor Farm, a local organic farm that sells produce, serves meals, and offers a variety of educational opportunities. Being a historic town, Three Oaks also has the Vickers Theater, a showcase for nearly a century of high-quality cinema.brbrbrbrAnother advantage of staying at The Fourth Oak is being quite near the many popular restaurants, galleries, and boutique shops of downtown New Buffalo, as well as several majestic, crystal-sand Lake Michigan beaches! Plus, you can enjoy the many activities afforded by being a short drive from the region’s largest recreational harbor— including boat and other watercraft rentals, fishing expeditions, day or evening cruises, and all sorts of woodland, lake, and riverside parks with hiking and biking trails galore. Lest we forget to mention, the stunning Warren Dunes State Park is close by, with its 2,000 acres of amazing sand dunes, beachfront, wetland trails, and extraordinary birdwatching! You and your guests might also relish visiting New Buffalo’s Oselka Park, which has baseball fields, playground equipment, and tennis courts. And for even more variety, nearby Union Pier also has a number of great restaurants, coffee shops, and breakfast spots. Plus, being so centrally located, there are plenty of nearby fun activities to keep you busy during your vacation, including:brbrbrbr• Local wineriesbrbr• Art galleriesbrbr• Antique shopsbrbr• Golf coursesbrbr…and more!brbrbrbrOther Things to Note:brbrTo ensure a safe and compliant stay, all guests are required to complete identity verification prior to check-in. A valid government-issued photo ID will be collected and verified, and the name on the ID must match the credit card used for payment. When applicable, a background screening may also be required as part of the booking process.brbrbrbrAll guests are required to review and sign Juniper Holiday + Home's Guest Occupancy Agreement prior to check-in. While we understand that events can affect your trip, it is our policy to stick to the agreed-upon cancellation policy in the listing. We recommend purchasing vacation travel insurance if you suspect you may need to cancel your reservation.brbrbrbrThe minimum age to rent this home is 25.brbrbrbrWe welcome up to 2 dogs at this home at no additional charge. Please include the number of pets you plan to bring or let our team know after booking. brbrbrbrOut of respect for our staff and their families, we do not permit check-ins or check-outs on Thanksgiving Day and Christmas Day. Thank you for your understanding.

Steps to Journeyman Distillery & Downtown 3 Oaks

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$918.68