Vacation Rentals By Owner In Three Oaks, MI

Four Seasons Retreat in Harbor Country offers luxury and charm on a lush, private acre. Enjoy a spa-like primary suite with porch access, two uniquely styled queen bedrooms, and an open-concept living space with modern design. The beautiful kitchen is fully equipped with a prep sink and bar seating. Unwind in the hot tub, lounge by the tranquil pond, or sip morning coffee on the dreamy screened-in porch. With hydrangea-lined gardens and elegant outdoor areas, Four Seasons is your perfect escape.

Four Seasons Retreat

Three Oaks, Michigan, United States

3

Bed

Bath

Sleeps

$1290.83

4 Bedrooms, 3.5 Bathrooms, Sleeps 08brbrNew Listing! brbrWelcome to Walnut Wowza, a gorgeous luxury vacation rental located in Three Oaks, Michigan, where privacy, style, and resort-level amenities come together for an unforgettable Southwest Michigan getaway. Tucked away in a peaceful, private setting, this beautifully decorated home is stunning both inside and out, offering the perfect escape for families, couples, or friends looking to relax and reconnect.brbrWalnut Wowza features four spacious bedrooms and three and a half bathrooms, comfortably sleeping up to eight guests. The interior is thoughtfully designed with elegant furnishings, curated décor, and inviting living spaces that feel both upscale and welcoming. Every detail has been carefully considered to create a space that is as comfortable as it is visually striking, making it easy to settle in and feel right at home.brbrStep outside and discover your own private outdoor oasis. The backyard boasts a private swimming pool, hot tub, and an outdoor firepit, creating the ideal setting for summer days in the sun and cozy evenings under the stars. A screened-in porch offers a relaxing space to enjoy morning coffee, afternoon lounging, or peaceful nights surrounded by nature. brbrPerfectly located near Lake Michigan beaches, local wineries, charming downtown Three Oaks, and the best of Harbor Country, Walnut Wowza offers the privacy of a secluded retreat with easy access to everything Southwest Michigan has to offer. Whether you’re planning a relaxing poolside escape, a wine country weekend, or a memorable family vacation, Walnut Wowza delivers luxury, comfort, and an exceptional setting for making lasting memories.brbrAll the amenities you would expect in a quality rental including private heated pool, hot tub, internet, central air and heat, washer/dryer, screened in porch, outdoor firepit and so much more!brbr**All Guests required to sign our Guest Occupancy Agreement as well. brbr**Minimum age of 30 years old to rent. brbr**Maximum six car parking.

Three Oaks Stunner With Private Pool & Hot Tub!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$1025.0

Simply Awesome…Harbor Country Cottage is a brand new (February 2019) 4 bedroom, 4 bathroom vacation home located in Harbert Michigan (between New Buffalo and Sawyer), a short walk to a beautiful private sandy Lake Michigan beach and minutes to the Warren Dunes, wineries, breweries, shops and restaurants! br brJust a short 80 mile drive from downtown Chicago, your vacation home is located in a peaceful neighborhood surrounded by towering pines, with a beautiful private sandy Lake Michigan beach just a short 1/3 mile walk away.brbrWalking up to the home you are greeted by a giant sunny front porch with relaxing rocking chairs – ideal for sipping your morning coffee/bloodies! Entering the front door, you’ll be blown away by the hickory plank floored, open concept – soaring 25’ ceiling kitchen/great room. The fully equipped kitchen is nearest the entry…very convenient for stocking your provisions for your stay. There is a oak country table seating 8 and an island seating 4 for your groups’ meals. br brThe living area is directly adjacent to the kitchen area so it is easy to grab a snack or drink while relaxing on the overstuffed sofas. The two story stone gas fireplace is perfect for taking the chill off cool evenings while relaxing with your party after a great day of beaching, or hitting the nearby establishments. There is a 58” 4K television over the mantel for that watching that wind down movie on Prime or Netflix. Or if it is a warm evening, enjoy the enormous screened rear porch with its dining table seating 8 and huge deep seating sectional seating area overlooking the wooded yard and ravine…so peaceful. br brUpstairs there is a spacious sunny seating area with a small loft area. There's another 4K television and the area is perfect for family board games or taking a sunny nap after reading your favorite beach novel. Here you will also find one of the two master bedrooms (king), which also has a daybed with trundle for the little ones. The bathroom is highlighted by a large freestanding tub for that relaxing soak. The other 3 bedrooms and bathrooms are on the main level. There is another master (king) with ensuite tiled bathroom, and two additional bedrooms (queens) and two more tiled bathrooms. br brOutside there is a large Weber gas grill, perfect for firing up those burgers or steaks and a fire pit for heating up those smores deserts while doing some great dark sky star gazing. The side porch has a outside hot shower for rinsing away the sand before you come in from your day at the beach. br brNeed to get out of the sun for a day, no worries there is plenty to entertain yourself with just a short drive away…breweries, wineries, a casino, shops, galleries, restaurants, orchards, blueberry patches and world class golf to name just or the few goodies. br brYour groups’ stay at Harbor Country Cottage is certain to be a memorable one and you will long for returning again soon.brbr

4 BR 4 BA Cottage - Walk to Private BEACH!!!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$241.0

Your home away from home in Three Oaks with 2 bedrooms and pull out bed to sleep 6 for larger families. This cozy cottage welcomes guests with its charming atmosphere and amazing location. Relax in the comfortable queen beds after a day of exploring the Journeyman Distillery, downtown shopping, and quant eateries of Three Oaks. The location is just a short drive to many beaches including the Michigan Dunes, breweries, wineries, and coffee shops. If you’re looking to unplug the cottage offers a big back yard with a fire pit, adirondack chairs, and games for all the family to enjoy. Take advantage of all that this cottage has to offer this spring and summer!!!

Charming 2-bedroom cottage steps to downtown Three Oaks, short drive to beaches

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$399.5

Welcome to Harbor Country and my woodsy cottage set on a 2 acre lot; just a short drive, walk or bike to several pristine beaches. Bike through wine country, enjoy local restaurants and stroll through the best of Michigan antiquing. brbrThe cottage is in top condition, all one level, with a doggy door accessible through the screened-in porch leading to 3/4 acre picket fenced yard. brbrThis cozy, colorful house is fully equipped with quality linens and kitchen accessories.brbrEnjoy rocking on the front porch or gather on the rear deck for a bbq, croquet and marshmallow roast over the fire pit.brbrLots to do in the area...or just 'be'. brbrJoin my Facebook Page to view many more pictures of cottage and become a 'Fan': Itsa DogslifebrbrbrKeywords: Cottage, wooded,dog friendly, lake michigan

'It's a Dog's Life - Unleash Your Fun Here!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$1027.45

On the LAKE side of Red Arrow at Cherry Beach. Lovely updated ranch home with a huge deck and yard. Enjoy stargazing from the quiet backyard deck. Roast s'mores in the firepit. Use all the toys and floaties in Lake Michigan at beautiful Cherry Beach!! The beach is a short, peaceful walk down Cherry Beach Road. brPerfect home for large families, reunions or groups of friends. We have hosted bridal parties, multi-generational family reunions, and many grandparents looking to gather their kids and grandkids for a week of togetherness. Many bedrooms make it easy to spread out. 4 bedrooms upstairs and lots of room downstairs for kids to bunk up. Local wineries, breweries, cideries and golf courses make Southwest Michigan a perfect vacation spot. New pickleball courts at New Buffalo High School! The Warren Dunes are a 5 minute drive. brCome relax and enjoy!!

Book your 2026 summer vacation week now! Saturday-Saturday lakeside rental.

Three Oaks, Michigan, United States

7

Bed

3

Bath

18

Sleeps

$280.0

A romantic getaway in a private wooded setting in the charming Village of Three Oaks sits in a secluded corner of a large lot with privacy fencing & its own driveway. This one bedroom cottage has vaulted ceilings & pine interior and was designed with a northwoods flair by local artist & owner Vincent. It contains several of his paintings & custom designed furniture.brbrOnly a 3 block walk to downtown Three Oaks, Journeyman's Distillery & Froelich's shops, restaurant, bakery/ coffeehouse, candy shop & wedding venue as well as a farmers' market, wonderful restaurants, unique shops, art galleries, a fine arts cinema, and a live performance theater, 2 major wedding venues and an organic distillery with world class putting greens designed after St. Andrews golf course in Scotland.brbrBeaches, Warren Dunes, kayaking, biking, hiking, wineries, breweries & all that Harbor Country has to offer are nearby.

Cherry Street Guesthouse with private wooded yard & firepit, 3 blocks to town!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$297.99

Backyard Oasis is a charming downtown Three Oaks retreat tucked on a quiet side street, perfect for families seeking a peaceful getaway close to shops and restaurants. Enjoy a well-equipped kitchen, cozy living area with a gas fireplace, and a screened-in dining patio. The grassy backyard offers room to play plus a fire ring with Adirondack chairs, creating an inviting spot to relax after exploring Harbor Country.

Backyard Oasis w Downtown Walkability, Fire Pit

Three Oaks, Michigan, United States

Bed

1

Bath

Sleeps

$398.33

A Four-Bedroom Retreat in the Woods - perfect for fallbrbrThis is the kind of place where mornings begin with coffee on the porch, afternoons stretch into long walks through the woods, and evenings end around a fire pit under the stars. With four bedrooms, two bathrooms, and six private acres to explore, the house is designed for families, friends, and anyone who wants a peaceful escape that still feels connected to good food, great company, and the beauty of the season.brbrThe Housebrbr4 Bedrooms, Sleeps 10brbrTwo king rooms with plush bedding and plenty of natural light.brbrOne room with two twins, perfect for kids or friends.brbrA camp-style bunk room in the basement with four twins — ideal for sleepovers and late-night laughter.brbr2 Bathrooms with soft towels and good water pressure ;) brbrLiving Spaces: A cozy living room with space to unwind, and an expandable farmhouse table that easily fits a large meal gathered from local farms or markets.brbrScreened-In Porch: For leisurely breakfasts, games of cards, or long dinners that stretch into the evening.brbrDeck Among the Trees: Perched just high enough to feel like a treehouse, perfect for reading, coffee, or quiet reflection.brbrFor Kids and FamiliesbrbrWe’ve stocked the house with activities so everyone feels at home:brbrOutdoor basketball hoopbrbrIndoor foosball tablebrbrA ninja rope course that keeps kids moving and laughingbrbrBoard games for cozy nights inbrbrSix Acres to ExplorebrbrThe property itself is an invitation to slow down. Wander wooded trails, kick through the leaves, or let the dog enjoy open space and fresh air. At night, gather around the fire pit for s’mores, stories, and star-gazing.brbrAutumn NearbybrbrFall here is crisp mornings, golden afternoons, and the simple joy of pulling on a sweater before heading out. Some local favorites:brbrDinges Farm: Apple picking, pumpkins, hayrides, and cider doughnuts that taste like fall itself.brbrNotre Dame Football: Just a short drive away — a perfect way to soak in the energy of game day.brbrJourneyman Distillery in Three Oaks: Whiskey tastings, local food, and a warm atmosphere.brbrLocal Wineries: Try Round Barn Estate or Tabor Hill Winery, both offering tastings and beautiful vineyard views.brbrCoffee & Food: Stop at Post Boi for coffee and pastries, or Staymaker at Journeyman for seasonal dishes.brbrHiking Trails Worth ExploringbrbrWarren Dunes State Park: Sweeping views of Lake Michigan, towering dunes, and trails through forest and sand.brbrGalien River County Park: Elevated walkways and a canopy tower overlook the river and wetlands, especially stunning in fall.brbrFernwood Botanical Garden & Nature Preserve: Peaceful trails surrounded by fall color, plus gardens to explore.brbrBreweries (That Welcome You and Your Dog)brbrGreenbush Brewing Co. (Sawyer): Known for hearty beers and a lively taproom.brbrGhost Isle Brewery (New Buffalo): Lake views, seasonal brews, and a dog-friendly patio.brbrHaymarket Taproom (Bridgman): Great pizza and a relaxed atmosphere.brbrMany of these breweries welcome dogs on their patios, so you don’t have to leave anyone behind.brbrDog-Friendly BeachesbrbrWarren Dunes State Park and Grand Mere State Park both have designated dog-friendly sections, perfect for a run along the water or a quiet walk.brbrWhy This HousebrbrThis retreat is designed to make fall feel unforgettable. Afternoons at the pumpkin patch, evenings around the fire pit, mornings watching the light shift through the trees. It’s a home that works just as well for a quiet weekend with your partner as it does for a lively gathering with family and friends.brbrAnd because it’s dog-friendly, you don’t have to leave your four-legged family members behind.brbrCome for the football games, the cider doughnuts, the hikes, and the crisp air. Stay for the cozy nights, the laughter around the farmhouse table, and the way fall feels when you’re surrounded by nature and good company

Newly updated wooded retreat near Three Oaks and Union Pier

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$255.79

2 Bedrooms, 1 Bathroom, Sleeps 4brbrLocated right in the heart of downtown Three Oaks, welcome to Artist Skylight Retreat! This two-bedroom, one full bath apartment is the perfect getaway for a couple or small family. This newly updated apartment has lots of light and close to everything. The gourmets in your group will love the fully stocked kitchen. Or cook outdoors with your gas grill. One bedroom with king bed and the other with a queen. Newly listed and two-night summer minimum, book today!brbrAll the amenities you would expect in a quality rental including internet, cable, central AC/heat, grill and more.brbr**All Guests Required To Sign Our Guest Occupancy Agreement.brbr**Minimum Age of 25 Years Old To Rentbrbr**Maximum Two Car Parking

Apartment

(Two Night Minimum!) Three Oaks Charmer Right In Downtown!

Three Oaks, Michigan, United States

Bed

1

Bath

Sleeps

$1572.47

7 Bedrooms, 4.5 Bathrooms, 2 Homes, Sleeps 16brbrPool Open Memorial Day-October 1st!brHot Tub Open Year-Round!brbrWelcome to your perfect getaway in the heart of Three Oaks, Michigan. The Cozy Oak is a beautifully appointed 7-bedroom, 4.5-bathroom vacation compound that comfortably accommodates up to 16 guests-ideal for family gatherings, group retreats, or special celebrations.brbrInside the house, you'll find a warm, inviting atmosphere with modern amenities, a fully equipped kitchen, spacious living and dining areas, and a wood-burning fireplace that adds a cozy touch on cooler evenings. The barn offers entertainment for both kids and adults, ensuring everyone stays engaged and relaxed. Multiple living areas and thoughtfully separated bedrooms provide families with flexibility and privacy between the house and barn. Two of the seven bedrooms are primary en-suites. brbrStep outside to your private oasis featuring a heated pool, hot tub, and a large outdoor firepit surrounded by mature trees and farmland—perfect for late-night s’mores and stargazing. Lounge poolside by day and gather around the fire at night- there’s plenty of space to relax and reconnect.brbrLocated just minutes from downtown Three Oaks, you’ll be close to charming shops, restaurants, wineries, and beautiful beaches of Lake Michigan.brbrCome to unwind or set out to explore, this one-of-a-kind retreat is designed for unforgettable moments.brbrThis property includes all the amenities you would expect in a quality rental including private heated pool, hot tub, gas grill, outdoor fire pit, wood burning fireplace, internet, central ac/heat, games rooms, washer/dryer, and more!brbr**All Guests Required To Sign Our Guest Occupancy Agreement.brbr**No Parties Or Events Allowed Without Permission.brbr**Minimum Age of 30 Years Old To Rentbrbr**Maximum Eight Car Parking

Gorgeous Estate With Pool, Hot Tub, and MORE!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$1051.17

Harbor Time is your getaway for private pool relaxation, game room fun & walkable Lake Michigan memories. brThe spacious pool has 6 lounge chairs, 2 tables with umbrellas & seating for 12, space for games like corn hole, mega jenga, etc. It's an easy 13 min walk or 3 min bike ride to the beach. Escape from the sun or rain in the climate controlled game room w/ ping pong, air hockey, foosball, pop a shot, arcade game, and it's own TV for watching the game. At night, relax in the hot tub or by the 2 gas fire pits. Plus, 2 screened in porches for eating & lounging! The public beach (Harbert Beach) is right down the road. Close to other beaches like Warren Dunes State Park, Weko Beach, and Silver Beach as well. With so many local attractions, restaurants, wineries, breweries and more, you are sure to find something suitable for a ladies getaway, friends outing, gentlemen’s weekend or entire family gathering! *Pool is heated and open from Memorial Day to Labor Day - Hot tub open all year*

Summer 26 Open! Pool, Hot Tub, HUGE Game Room, short walk to Beach!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$649.25

Sycamore Guesthouse, where contemporary furnishings meet within a restored 1880's Victorian home with all modern conveniences for today's needs. Each of the 5 bedroom suites has its own private bathroom with modern Euro showers. Beds are queen luxury mattresses & quality linens set upon modern upholstered platform beds. There are 5 queen beds, 2 full/double beds and 1 pack-n-play crib giving room for 14 adults + children. Just across the street from Journeyman Distillery. We offer your group 5+ bedrooms & 5-1/2 private baths. The covered wrap-around porch is the perfect place to see and be seen as we are located in the heart of Three Oaks Village. The kitchen is well stocked and equipped for most every cooking / preparation needs. We also offer an outdoor gas grill, yard & fire pit May-October (we do not supply firewood.) Outdoor security cameras (2 on porch, 1 at garage and 2 in yard) and video doorbell are dis-armed during your stay.

Sycamore Guesthouse, Sleeps 14+, Steps to Journeyman Distillery!

Three Oaks, Michigan, United States

5

Bed

5

Bath

14

Sleeps

$293.62

Get away in style to the Cherry Tree Cottage located in a quiet corner of Three Oaks. You’ll enjoy a private home with a large, fenced-in yard that backs up to mature woods and is walking distance to the charming shops, restaurants and event venues in town including Journeyman Distillery and the Acorn Theater. The location is central to all that Harbor Country has to offer - New Buffalo’s beaches are a 10-minute drive, Warren Dunes State Park is 15 minutes away, and there’s convenient access to the Galien River for kayaking or paddle boarding. The area is also close to many vineyards, as well as hiking and biking trails, and local farm stands will provide the freshest ingredients if you choose to cook while you’re away! brbrThe kitchen is well-appointed for preparing all types of meals and provides coffee lovers with many options in the morning- Keurig, drip coffee, French press or Chemex. There’s even an ice cream maker to take the edge off of a hot summer day and a slow cooker for making soups and stews for tailgating in the Fall. The back door opens to a sizeable deck with a grill nearby and a hot tub that seats 6. The yard is perfect for lawn games (corn hole is provided) or for your well-behaved, four-legged best friend to enjoy. In the evening, you can relax with your favorite beverage around the fire pit, take a dip in the hot tub, or gaze at the stars when the sky is clear. There are three bedrooms - 2 with Queen beds and a third with a daybed/trundle that provides 2 twins, and there’s a washer and dryer for your use. For entertainment, the home offers board games, cards, books, high speed Internet, YouTube TV with local and cable channels and Roku/Smart TV to access streaming apps.brbrPet policy:brbrWell-behaved dogs are welcome at the cottage (limit 2) - I love to travel with my dogs, too! - and I'm asking that guests follow these rules to keep the cottage clean and welcoming for other guests who may have pet sensitivities:brbr1) Please do not allow pets on the furniture unless it is covered - covers are provided and are washed between guest stays. br2) Pets should not sleep on the beds - please use one of the 2 dog beds provided or your own.br3) Dog bowls are available and should be used for all feeding/drinking - please do not use other dishes for your pets.br4) Please wash/bathe dogs outside.br5) Please use the paw wipes that are provided at the front and back doors.br6) Please clean up after your pet in the yard - this will keep there are bags provided and a trash can right outside - as well as a scooper.

Charming Three Oaks Cottage - dog friendly with a fenced yard and hot tub!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$393.71

Located steps from the Village of Three Oaks, guests can walk to Vickers Theatre, Featherbone Factory, Acorn Theatre, Froehlich’s, Journeyman Distillery, and more. Great for cyclists, and for food or wine enthusiasts, located in the heart of Harbor Country - short drive to Lake Michigan, Warren Dunes, 8 wineries, shopping and 2 casinos. brbrThe cottage has been professionally designed with bright, cottage decor with a modern twist. Kids and adults will enjoy climbing the 'dock' ladder to the comfortable sleeping loft which is 6' tall in the middle. The loft features three twin beds a television, and VCR. brbrFor the family chef, the kitchen features a professional Aga range and farm house sink. Enjoy breakfast on the back sun-porch or watch the game during the fall on one of our flat screen TV’s. brbrPamper yourself in the master bathroom with vintage marble sink, mosaic tile floors and euro-style shower.brbrEnjoy the vintage touches like fully restored doors, hinges, cast-iron vents, chandeliers, high ceilings and hardwood floors throughout.brbrbrKeywords: cottage, house, town, wineries, three oaks, harbor country, pet friendly, loft, lake Michigan, new buffalo, theaters, shops, restaurants, cycling, brewery, antiques, renovated, new, clean, four winds casino, Journeyman, Acorn Theater, Three Oaks, New Buffalo

Cottage In The Heart Of Harbor Country - Steps From Town

Three Oaks, Michigan, United States

3

Bed

Bath

10

Sleeps

$1477.43

Welcome to the newest offering from Michigan Family Retreats, thoughtfully designed for multi-generational family vacations, reunions, and quiet group getaways. Set on 35 wooded acres near Three Oaks, Michigan, this peaceful property offers space to reconnect, explore nature, and enjoy time together.brbrFamilies can spend the day walking private woodland trails along the Galien River and Johnson’s Creek, swimming in the saltwater pool, or playing pickleball and basketball on the multi-sport court. Evenings are perfect for gathering in the 45 ft. screened pavilion, sharing meals and stories surrounded by the quiet beauty of Southwest Michigan. Despite the secluded setting, you’re just 15 minutes from Lake Michigan beaches and the restaurants, wineries, breweries, and art galleries that make Harbor Country one of the Midwest’s favorite vacation destination.brbrOutdoor Amenities:brDesigned so families can enjoy the outdoors together all day long, in any season.brbr• 41 x 16 ft. saltwater swimming poolbr• Hot tubbr• Full-size pickleball/basketball/volleyball court with adjustable netbr• 32 acres of private wetland with trails along Galien River and Johnson’s Creekbr• Open field for soccer, baseball, or family gamesbr• 45 ft. screened pavilion with fireplace, lounge and dining spacebr• Pavilion kitchenette with sink, dishwasher, beverage refrigerator and Weber BBQ grillbr• ChargePoint EV2 charger for those with electric carsbrbrThe Home:brA perfect environment for everyone to comfortably gather for longer family stays.brbr• 6 bedrooms, 4 with private en-suite bathroomsbr• Additional full bathroom near the kitchenbr• Blackout shades in every bedroombr• Large chef’s kitchen with high-end appliancesbr• Two dishwashers (ideal for large groups)br• Dining room with custom 12-foot dining tablebr• Bright living room with 85” TVbr• Separate office workspacebr• Game room with foosball and bumper poolbr• Two washers and two dryersbr• High-speed WiFibr• Large windows throughout the home overlook the property and surrounding woods.brbrExplore Three Oaks & Harbor Country:brWhile many guests find there's so much to do on the property that they rarely want to leave, Southwest Michigan’s Harbor Country is a favorite destination for relaxed vacations just 90 minutes from Chicago. Nearby attractions include:brbr• Lake Michigan beaches, 15 minutes awaybr• The charming town of Three Oaks with restaurants and shopsbr• Local wineries, breweries, and cideriesbr• Art galleries and antique shopsbr• Farm markets and seasonal festivalsbrbrPerfect For:brbr• Family reunionsbr• Multi-generational vacationsbr• Large family getawaysbr• Quiet group retreatsbrbrTo preserve a peaceful environment, we enforce a strict no party policy. The booking platform will be contacted immediately upon any noise violations, disruptive gatherings, or arrival of unauthorized guests. Several family members have strong to severe animal allergies. For this reason, we cannot allow any pets into our home.

35-Acre Retreat | Pool, Pickleball & Private Woods

Three Oaks, Michigan, United States

Bed

Bath

17

Sleeps

$1300.0

Welcome to The Modern Oak, your modern retreat in the heart of Three Oaks, Michigan. Perfectly located just steps from downtown and right across from Journeyman Distillery & Restaurant, this stylish home offers the perfect mix of comfort, luxury, convenience, and small-town charm.brbrWhether you’re here for a family getaway, a weekend with friends, or a cozy couples’ escape, or a wedding stay, The Modern Oak is designed for relaxation in every season.brbrThe SpacebrbrStep inside and unwind in our bright, open-concept living area, where modern design meets cozy comfort.brEnjoy the ambiance of the indoor fireplace, gather around the spacious dining table, or cook your favorite meals in the fully equipped kitchen.brbr•3 king-size bedrooms each with an en suite bathroom, plus an additional bedroom perfect for kids, with 2 sets of bunk beds (Full/Twin) with an en suite bathroom — sleeps up to 10 guests and more. br•One of the king bedrooms is located on the main level for easier access, ideal for those who prefer not to use stairs.br•Spacious open-concept living area, fully equipped kitchen, and cozy indoor fireplace make this home perfect for your group.brbrAmenitiesbrbr•Hot tub & fire pit available year-round br•Early check-in and late checkout available at no additional cost (when availability allows)br•Smart TV and high-speed Wi-Fibr•Free on-site parking (3 cars max)brbrLocation Highlightsbrbr•Right across from Journeyman Distillery & Staymaker Restaurantbr•Steps from downtown Three Oaks — explore local cafés, restaurants, bars, shops, and art galleriesbr•Quick drive to beautiful Lake Michigan beaches (Town Line Beach-Harbert Beach-Cherry Beach), lush Orchards & farm‑stands, scenic state parks like Warren Woods State Park with hiking trails, and charming nearby towns for exploring seasonal fun.br•Close to wineries, hiking trails, and seasonal festivalsbrbrHouse RulesbrbrTo ensure every guest enjoys a clean, relaxing stay at The Modern Oak, we kindly ask that you help us maintain a comfortable environment for all.brbr• Please no pets — we want to keep the space fresh for everyone.br• No smoking/vaping inside the home, or ***ANYWHERE ON THE PROPERTY***br• Please remove your shoes upon entering for cleanliness and comfort — you’re welcome to bring slippers.brbrWe appreciate your cooperation. To uphold these standards, a $500+ fee may be applied for any violation of the no‑pets or no‑smoking/vape policy.brbr Perfect for Every Season brbr• Winter: Soak in the year-round hot tub or cozy up by the fireplace after a snowy day exploring Harbor Country br• Spring & Summer: Gather around the fire pit under the stars or relax in the hot tub — the perfect way to unwind after a day of adventure or beach days br• Fall: Savor the crisp air, visit nearby wineries, orchards, or pumpkin patches, and take in the vibrant fall colors

The Modern Oak Lux Getaway Steps from Journeyman

Three Oaks, Michigan, United States

Bed

Bath

10

Sleeps

$1104.07

Summary:brbrSet on 2 acres in Three Oaks, Cozy Haven offers a more refined Southwest Michigan stay near Cherry Beach, Gordon Beach, and Pier Road Public Beach. The setting feels private, the interiors are beautifully updated, and the layout suits weekends with friends, family beach trips, and longer stays alike. Time here can shift easily from the shoreline to dinner at the house, with a pergola for evening hours outside and a dedicated workspace that adds flexibility for longer visits.brbrbrbrThe Space:brbrInside, the house has a fresh, polished look. Sliding glass doors open the main living area to the deck with outdoor dining seating, and the fireplace gives the living room a serene ambiance after dark. The kitchen sits at the center of the house with white cabinetry, stainless appliances, open shelving, and a large island with seating. Just beyond it, the dining area faces the property through wide windows, keeping the setting in view throughout the day.brbrbrbrThe bedroom layout suits a full group well. The primary suite includes a California king bed, a large ensuite bath, and direct access outside. Another bedroom has a king bed, while a third offers a queen. The bunk room includes two twin bunk beds. In the fifth bedroom, a daybed and dedicated workspace make it easier to extend the stay without losing time to email or a call.brbrbrbrMaster Bedroom: California King BedbrbrBedroom 2: King BedbrbrBedroom 3: Queen BedbrbrBedroom 4: 2 Single Bunk BedsbrbrBedroom 5: Day Bed (single) with dedicated workspacebrbrbrbrThe bathrooms continue the updated finish found throughout the house. The primary bath includes a soaking tub and double vanity, while the additional baths are finished with walk-in showers and a clean, polished look. A separate laundry room with washer and dryer is also available for guest use.brbrbrbrOutside, the front pergola creates an inviting place to settle in after the beach, the back deck is an awesome spot for casual dining, and the large yard adds to the sense of privacy across the property. With 2 acres to enjoy, the setting feels calm and removed, even with some of the area’s best public beaches just minutes away.brbrbrbrLocated in the heart of Harbor Country, Cozy Haven places you close to everything Southwest Michigan has to offer. Spend your days relaxing on nearby Lake Michigan beaches like Cherry Beach, Gordon Beach, and Pier Road Public Beach, exploring the shops, galleries, and restaurants of Three Oaks, and visiting local wineries, breweries, and distilleries. Enjoy farmers markets, antique shopping, biking scenic backroads, hiking nature trails, golfing, and seasonal events plus easy access to Union Pier, New Buffalo, and Sawyer for even more to explore.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. brbrbrbrParking is available in the driveway for up to four vehicles. The barn and garage are not accessible to guests.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.brbrbrbrPermit No: STR-25-0377

Cozy Haven Near Lake Michigan Beaches on 2 Acres

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$1228.31

Located on a quiet side street in Harbert, this large four-bedroom, four-and-one-half-bathroom house is a great family vacation getaway. It is a short half-mile walk or ride to the Harbert Road beach access point. This house has a private outdoor heated pool and hot tub, a beautiful vintage pool table, a wet bar, and a vast outdoor area. The main floor includes two large living areas at opposite ends of the house. A spacious kitchen, dining area, and family room are on one end. The dining area features a rustic grain wood table with seating for 10. A comfortable seating area has a leather sectional couch, coffee table, three cozy club chairs, and a flat-screen smart TV. The kitchen is fully equipped with new high-end stainless steel appliances, plenty of counter space, and a convenient breakfast bar with seating for four. The entertainment area on the opposite side of the house is perfect for socializing and relaxing as it boasts a sit-down wet bar, pool table, poker table, and a lounge area with a spacious sectional couch with a flat-screen smart TV. The house is bathed in natural light, with numerous windows, skylights, and sliding doors leading outdoors. A powder room is located off the back entertainment area. A metal spiral staircase leads from the entertainment area to a roomy loft area, the first of two primary bedrooms in this house. This upstairs primary bedroom includes a king bed with an ensuite bathroom featuring a Jacuzzi tub and walk-in slate shower. This upstairs primary bedroom exits to a private deck with a backyard view and nearby woods. On the first floor is another primary bedroom with a king-size bed and ensuite bathroom featuring a Jacuzzi tub and walk-in shower. This first-floor primary bedroom has a sliding door to a deck leading to the backyard. Two more bedrooms are on the first floor, each with a queen bed. There are two full bathrooms adjacent to these bedrooms. One bathroom has a shower, and one has a tub/shower combination. Also located on the main floor is the new laundry room with a new washer and dryer. A first-floor office has a pull-out queen-size sleeper sofa and a closet. Outdoor amenities include a large, beautifully landscaped yard with numerous chaise lounges and a new sectional sofa seating area with an enormous sun umbrella. The yard's centerpiece is a new built-in heated pool (16 by 40 feet) with an automatic cover. Adjacent to the pool area is a hot tub. There is a deck with a large barbeque grill. There are two outdoor tables with seating for eight and six, respectively, for al fresco dining. There is also a Solo stove for outdoor fires. The hot tub and pool are available if you book the home between May and September. The house is fitted with a whole-house generator in case of a power outage.brbrLake Michigan Harbert Beach is nearby – a short stroll down a quiet road to Harbert Beach. There is some parking for Harbert Beach. Cherry Beach is just around the corner if you prefer and has lots of parking if you bring beach toys, coolers, etc. Within walking distance up Harbert Road in the opposite direction of the beach is Luisa's Swedish Bakery. A fantastic local coffee shop called Red Arrow Roasters is at the end of Peach Street. They have the best coffee and their famous biscuits with butter. All that Harbor Country has to offer is just minutes away - wineries, breweries, shops, and restaurants; then return to relax in our refuge nestled in a serene area surrounded by nature.brbrThis home is equip an entire home generator that will power the pool, spa and the entire home in the case of a power outage.

Harbert Hideaway - A 4 min walk to the beach with private pool and hot tub.

Three Oaks, Michigan, United States

5

Bed