Vacation Rentals By Owner In Three Oaks, MI

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

$176.27

1 Bedroom, 1 Bathroom, Sleeps 2brbrTwo Night Summer Min!brbrLocated in the charming town of Three Oaks, we welcome you to The Louis. This one-bedroom, one-bathroom multi-unit is a short walk to downtown Three Oaks and a ten-minute drive to the beach. One of three units in this spacious property and can be rented in conjunction with the other two to sleep 12 total. brbrCozy and romantic, nice space for a couple's getaway. Main floor bedroom has queen bed and updated bathroom with shower. Mini kitchen with microwave and fridge as well (no sink or stove). Dining area and study nook completes this unit. brbrAll the amenities you would expect in a quality rental including internet, gas grill, and more.brbr**All Guests required to sign and return our Guest Occupancy Agreement. brbr**Minimum age of 25 years old to rent.brbr **Maximum one car parking.

Guest House

Three Oaks Unit Steps To Downtown! 2 Night Summer Min!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$319.96

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

Bed

Bath

Sleeps

$983.32

Welcome to The Parish House — In the heart of Three Oaks and 10 minutes from Lake Michigan!brbrThis is where wedding mornings begin.brbrWhere friends and family gather to enjoy catching up. brbrWhere champagne is poured before the vows.brbrWhere families linger longer at the table.brbrWhere Notre Dame weekends turn into cherished traditions.brbrThe Parish House isn’t just a place to stay — it’s where unforgettable moments unfold.brbrA Historic Landmark, Completely ReimaginedbrbrOriginally built 100 years ago as a church parish, this extraordinary home has been meticulously and completely renovated — preserving its architectural soul while elevating every detail to modern luxury standards. The perfect sanctuary for relaxation and rejuvenation.br Nestled in the charming Village of Three Oaks, you’re steps from restaurants, wedding venues, art galleries, and antique shops — yet tucked into a quiet setting that feels entirely your own. And when the lake calls, the breathtaking shoreline of Lake Michigan is just 10 minutes away.brbrStep through the dramatic 8-foot iron doors and feel it immediately:brbr• Original 100-year-old hardwood floorsbr• Soaring 12- and 22-foot ceilingsbr• Elegant sconce lightingbr• Grand open-concept living spacesbr• A warm gas fireplace anchoring the roombrbrThe scale is impressive.brThe atmosphere is intimate.brThe experience is unforgettable.brbrFive Private King Suites — Boutique Hotel ComfortbrbrEvery bedroom is a retreat:brbr• King-size beds with plush, high-end linensbr• Private ensuite bathroomsbr• Soft robes and generous closetsbr• Fully stocked baths with premium essentialsbrbrAll bathrooms are fully stocked with hairdryers, plush towels, shampoo, conditioner, face soap, and body wash.brbrOne king suite includes a trundle with two twin beds — perfect for families who want to stay together without sacrificing comfort.brbrThe beautifully finished lower level adds incredible flexibility with:brbr• A full second kitchenbr• Two full bathroomsbr• Two double XL bunk beds (four beds total), accommodating four comfortably — or up to eight if sharing. We also have blow-up mattresses for kids or adults!brbrThere is space for everyone — without ever feeling crowded.brbrA Chef’s Kitchen Made for CelebrationbrbrAt the heart of the home, the show-stopping kitchen was designed for gathering:brbr• 16-foot statement islandbr• Double refrigeratorsbr• Three dishwashersbr• Oversized dual-fuel gas rangebr• Walk-in pantrybr• Dedicated bar areabrbrIt flows seamlessly into expansive dining and living spaces beneath dramatic 22-foot ceilings — the perfect setting for rehearsal dinners, holiday feasts, and late-night conversations that stretch for hours.brbrDesigned for Elevated GatheringsbrbrPerfect for:brbr• Wedding weekendsbr• Multi-family vacationsbr• Notre Dame game daysbr• Family reunionsbr• Harbor Country escapesbrbrWhen you’re ready to explore, nearby Warren Dunes and Cherry Beach invite you to enjoy sandy shores and peaceful waters. Notre Dame fans will love that the stadium and South Bend Regional Airport are just 30 minutes away.brbrWith high-speed WiFi, full HVAC comfort, a fitness area, and thoughtfully designed gathering spaces, The Parish House delivers both luxury and ease.brbrSpend the morning strolling into town for coffee.brSpend the afternoon at Warren Dunes or Cherry Beach — just minutes away.brSpend the evening around the table, together.brbrThis is Harbor Country at its finest.brbrNeed additional space We also own the neighboring home at 7 Linden — a beautifully appointed 3-bedroom (1 king, 2 queens), 2-bath property featuring a hot tub and fire pit.brbrWith additional curated rentals along Linden Street, wedding parties and extended families can stay steps from one another while maintaining privacy.brbrWe lovingly call it “Love on Linden.”brbrOur StandardsbrbrTo preserve the elevated experience for all guests:brbr• No parties unless limited strictly to registered overnight guests and must be approved in advance with an extra deposit.br• No petsbr• No additional guests beyond your reservationbr• Primary renter must be 28+ unless holding 5-star reviewsbrbrThe Parish House is for those who value beauty, comfort, and meaningful gatherings — not party crowds unless it is for staying guests only.brbrLuxury homes of this scale and character in Harbor Country are rare — especially this close to Lake Michigan.brbrIf your dates are available, we encourage you to secure them.brbrWe would be honored to host you at The Parish House.

Timeless Architecture. Completely Modernized Luxury. Heart of Three Oaks!

Three Oaks, Michigan, United States

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Bath

Sleeps

$367.34

3 Bedrooms, 1 Bathroom, Sleeps 6brbrTwo Night Summer Min!brbrLocated in the charming town of Three Oaks, we welcome you to The Lincoln. This three-bedroom, one-bathroom multi-unit is a short walk to downtown Three Oaks and a ten-minute drive to the beach. One of three units in this spacious property and can be rented in conjunction with the other two to sleep 12 total. brbrEnjoy your coffee in the gorgeous screened-in porch or cook your meal on the gas grill. The main floor has dining for six in their fully stocked kitchen (no dishwasher). Kick back and relax in the tv room, perfect for spending time with loved ones. Primary bedroom has king bed and access directly to screened-in porch. Second bedroom with queen bed and third bedroom with twin over full bunk bed.brbrAll the amenities you would expect in a quality rental including internet, gas grill, screened in porch, washer/dryer and more.brbr**All Guests required to sign and return our Guest Occupancy Agreement. brbr**Minimum age of 25 years old to rent.brbr **Maximum three car parking.

Three Oaks Home Close To Everything! Two Night Summer Min!

Three Oaks, Michigan, United States

Bed

1

Bath

6

Sleeps

$857.5

Welcome to Lakeside Landing – a renovated 3-bedroom, 2-bath retreat in the heart of Lakeside, just a short bike ride to Lake Michigan. Thoughtful design, curated furnishings, and a private outdoor oasis make this home the perfect choice for families, couples, or small groups looking for comfort and style in Harbor Country. And just 35-40 minutes to South Bend/Notre Dame! brbrBedrooms & Bathrooms:br-3 spacious bedrooms, sleeping up to 8 guests comfortablybr-2 full bathrooms, each with a double vanity for added conveniencebr-Calming tones, layered textures, and local, unique décor throughoutbrbrLiving Spaces:br-Open kitchen with double oven, open shelving, and full cookware set – ideal for holiday meals or cozy nights inbr-Expansive screened-in porch with vaulted ceilings, heaters, and space to dine or lounge, even in cooler monthsbr-Fireplace, smart TVs, and high-speed Wi-Fi for game nights, streaming, or simply unwindingbrbrOutdoor Features:br-Private pool (heated, open May–September; October availability by request)br-Year-round hot tub – perfect for crisp fall evenings or snowy winter nights under the starsbr-Fenced backyard with fire pit and seating, designed for everything from summer s’mores to autumn wine nightsbr-Bikes for guest use to explore Pier Street and Cherry Beach, or nearby towns like Union Pier, New Buffalo, and Three OaksbrbrDesigned for All Seasons:br-Fall: Take in the colors of Harbor Country, enjoy winery tours, and return for hot tub soaks and fireside evenings.br-Winter: Gather for holiday dinners, relax in the hot tub, and cozy up in the porch or by the fireplace after exploring charming local shops and snowy trails.br-Summer: Spend your days at the beach or by the pool, and evenings on the porch or around the fire pit.brbrPet Friendlybr-Pets are welcome, so the whole family can enjoy Lakeside together.brbrNote: Pool is open May–September (heated); please inquire about October use. Hot tub is available year-round.

Lakeside Retreat – Renovated & Charming 3BR with Pool & Hot Tub

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$559.96

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

Bed

Bath

Sleeps

$275.33

Located 0.8 miles from the center of Village of Three Oaks, guests can walk to Vickers Theatre (0.8mi), Featherbone Factory, Acorn Theatre, Froehlich’s, Journeyman Distillery, and more.brRestaurants worth visiting: Oaks eatery for breakfast, Froehlich’s restaurant, Froehlich’s Bakery, Historian Restaurant located in Sawyer, Michigan and more.brWe are only a 35 minute drive to Norte Dame. brbrClose to snowmobile trails.brbrYou’ll find a unique mix of shops, distilleries and wineries, restaurants and quaint bakeries, historic sites, museums, theaters, and plenty of outdoor activities in Three Oaks.brbrGreat for cyclists, and for food or wine enthusiasts, located in the heart of Harbor Country - short 12 minute drive to Lake Michigan, Warren Dunes, Hesston Steam Museum, 8 wineries, shopping and 2 casinos.brbrIf you need to rent a bike, check out Jackson Family Cycle located at 110 N. Elm St. Three Oaks, MI 49128 Phone: 269-612-7511.brbrbrKids will enjoy 2 twin trundle beds in one room for a slumber party.brbrEnjoy breakfast on one of the 2 picnic benches in the large back yard.brbrPick a bucket of flowers to bring home at Homecamp Flowers just 5 minutes away. They are open Friday - Saturday 10:00 am to 4:00 pm. Located at 6658 Three Oaks Road, Three Oaks, MI, 49128brbrMake your way to this darling, well-maintained home located just southeast of downtown Three Oaks.brbrTucked away on a quiet street, this charming vacation rental is ideal for small families who want a quiet getaway while still being within walking distance of shops and restaurants, and only eight miles from the New Buffalo Public Beach on Lake Michigan.brbrInside this one-story ranch, you'll find a well-equipped island kitchen with counter seating, a large sectional sofa, and a flat-screen TV for streaming your favorite channels.brbr Right off the kitchen, there is a grill and 2 picnic benches for you to enjoy in the spacious backyard.brbrThe grassy backyard backs up to a farm field is great for the kids, play Cornhole bag toss game, and is the perfect spot to close out each day as the stars come out.brbrThings to KnowbrbrFree high-speed WiFibrbrBedroom #1 has a king-size bed with flat screen tv.brbrBedroom #2 has a queen size bed.brbrBedroom #3 has 2 twin trundle beds.brbrWalk-in shower in the bathroom.brbrNo stairs for guests to climb.brbrTV streaming services require guests' own accountsbrbrElectric Stove (no gas range) propane grill in yard. Bottle water dispenser provide for drinking because the water supply from the city is well water.

Three Oaks, Michigan. Beautiful Southwestern Michigan

Three Oaks, Michigan, United States

Bed

1

Bath

8

Sleeps

$307.69

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

$556.52

4 Bedrooms, 2.5 Bathroom, Sleeps 10 brbrPool Open May 23-October 01st!brHot Tub Open Year-Round!brbrLocated in the charming community of Harbert we welcome you to Lakewood By The Lake! This home is the perfect getaway for your family and friends!brbrKick back and relax in your private heated pool. Unwind in the hot tub, open year-round. Roast smores under the stars in the outdoor firepit. Have a pickup game of hoops with your outdoor basketball hoop. Plenty of outdoor seating with gas grill for your next great meal. Wash the day's sand away with the outdoor shower. Just a short walk to Cherry Beach which boasts 500 feet of sandy frontage! Close to everything in Harbor Country.brbrRanch style house has lots of room for everyone. Fully stocked kitchen with dining table for eight and island seating for four. For those cooler autumn evenings, cozy up to the wood-burning fireplace in the spacious TV room. Kids and adults alike will love the games room with foosball and air hockey! Primary bedroom with king bed an en suite full bath. brbrAll the amenities you would expect in a quality rental including private heated pool, hot tub, outdoor firepit, internet, cable, fireplace, washer/dryer, central AC & heat, games room, basketball hoop, and more! New listing so calendar is open, book today!brbr**All Guests Required To Sign Our Guest Occupancy Agreement.brbr**Minimum Age of 25 Years Old To Rentbrbr**Maximum Five Car Parking

Lakeside Home With Pool & Hot Tub! Close To Beach!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$866.72

Summer 2026 Calendar Open! Only a few weeks left (July 17-24, Aug 14 -21 and Aug 21-28)!brbrGet away to Harbor County on this private ¾ acre, open concept home two blocks from Cherry Beach with a large, heated pool and hot tub! Heated pool opens mid-May thru end of September and hot tub open year-round! Have an electric vehicle You can charge your vehicle at our property with a universal charging station.brbrCheck out our new rental: Warren Woods Retreat (Property ID: 2621249)!brbrWe want our guests to know we are committed to providing you a clean and safe vacation experience. Our cleaning and pool services are following CDC recommendations for cleaning and maintenance.brbrThis home has an open floor plan with natural light filling the spacious living areas. A stone fireplace anchors the living room which opens to a large dining area overlooking the pool and a beautifully updated chef’s kitchen with large island. brbrMain floor primary suite has walk in shower, soaking tub, and heated floors. Upper lounge area is perfect for games or movies. Two additional large bedrooms upstairs means room for family and friends. brbrRelax in the three seasons room or step out to a ‘15x45’ heated saltwater pool for a swim, soak in the hot tub, fire up the built-in gas grill, or roast marshmallows in the firepit. With a ¾ acre lot, you’ll have plenty of privacy and space to play. brbrOnly a few minutes walk to Cherry Beach, and short drive to the Warren Dunes, downtown New Buffalo and many great breweries, wineries and unique restaurants! brbrThis is a great space for all seasons. Our extended family also enjoys this property frequently, so please contact me if you have any questions.brbrThis home has many great features including:br• Walk to a great beach. Only a short walk to Cherry Beach, one of the largest and most sought-after beaches in the Harbor County area.br• Large heated salt water pool (‘15x45’) in a private wooded setting with plenty of sun.br• Hot tub is open all season and is a ton of fun in the fall and winter months too.br• Home sits on a private ¾ acre lot, which offers lots of privacy, sun, and space to play.br• Outdoor fire pit.br• The entire home has been recently updated, with high end finishes throughout. br• This home is open concept and is large and comfortable for groups of 10 or more (set up to comfortably sleep 10).br• Fully equipped chefs’ kitchen is large and offers a professional grade gas range and large island. Large build in gas grill is the back yard too. br• We have plating for 12+ (i.e. dishes, silverware, glasses, etc.)br• Dining table is large and set for 8, but can easily seat 10. Large island seats 4. Three seasons room off the kitchen has large round table which seats 6 to 8.br• Comfortably sleeps 10. First floor master suite with king bed. Two large bedrooms upstairs each with a queen bed and daybed with pullout trundle (see pictures). br• Open loft with TV for movies and Wii game system. Sofa in loft can pull-out to a twin bed. br• A pack and play, two cots, air mattress, and two high chairs are also available. br• We have a basketball hoop, bags, bikes for kids, and lots of board games and puzzles.br• Large circular driveway offers plenty of parking (6+ cars)br• Minutes (drive) to Warren Dunes and many great breweries and wineries. This makes for a fun afternoon.br• There are also many excellent restaurants nearby. See our Cherry Beach Pool House website for our recommendations.br• This is a great space for all seasons. Our extended family also enjoys this property frequently, so please contact me if you have any questions.

Private Cherry Beach Pool House with large heated pool & hot tub!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$430.0

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

$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

5

Bed

Bath

12

Sleeps

$460.57

4 Bedrooms, 1.5 Bathroom, Sleeps 8brbrThree Night Summer Minimum!brbrJust steps away from Journeyman Distillery and lovely downtown Three Oaks, we welcome you to The Greenskeeper's House! This four bedroom, one and a half bath home is perfect for your next getaway. brbrMain floor has family room with big screen television. brFully stocked kitchen and dining for six at table. Main floor bedroom has queen bed. brbrSecond floor with three bedrooms, two with queen beds and one with a king. Bathroom on this floor as well. brbrAll the amenities you would expect in a quality rental including gas grill, washer/dryer, internet, outdoor firepit, and more. brbr**All Guests Required To Sign Our Guest Occupancy Agreement.brbr**Minimum Age of 30 Years Old To Rentbrbr**Maximum Four Car Parkingbrbr**Journeyman music can play until 11pm EST. It is possible you may hear. brbr**Guests do not have access to garage but Journeyman crew may access for lawn equipment during your stay. brbr**Can Be Rented In Conjunction With Journeyman Distillery Flat, Journeyman Bunkhouse and Journeyman Distillery Farmhouse.

Three Oaks Home With Three Night Summer Min!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$491.21

Three Oaks RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrJust outside the charming village of Three Oaks, this elegant family retreat offers a quiet escape with easy access to Lake Michigan attractions. Newly remodeled and refurnished, this three-bedroom/two-bath boasts multiple living areas and modern amenities including free WiFi, central AC, and a private washer/dryer. Sip coffee or just while the days away in the front porch rockers and for lunch, fire up the private gas grill for a family barbecue on the back deck. The firepit is perfect for happy hour and and evening S'mores. Whether its to start off your day or to cap it off, there's never a bad time for a relaxing soak in the private hot tub.brbrThe bright, updated interior is tastefully appointed with contemporary fixtures and appliances with strong natural lighting featured throughout. The main floor living room equipped with a large, flatscreen smart TV opens to an airy dining area with seating for six and beautiful bay windows offering pastoral views of the surrounding farmland. The kitchen is well-equipped for family cooking with updated, stainless steel appliances, including a dishwasher for easy cleanup. Specialty items including a pizza stone and a full suite of utensils make the culinary options virtually endless! Two bedrooms share a full bathroom on this floor.brbrDownstairs, a semi-finished basement features a second living area with a sofas, loungers, and table seating. Choose from one of the classic board games and host a family game night!brbrThe upstairs primary suite offers multiple sleeping options with a king and two double beds and an en suite bathroom with a luxurious jetted tub and separate shower. A sunny desk/workspace is perfect for quiet work or study.brbrThings to KnowbrFree WiFibr1 dog welcomebrFor an additional sleeping option, there‚Äôs a queensofa bed in the living roombrPlease adhere to our 'Good Neighbor' policy; No Parties; Quiet Hours enforcedbrbrThis property is managed by Vacasa Michigan LLCbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Family Home with Porch & Deck, Private Hot Tub, Firepit, & Fast WiFi - 1 Dog OK

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$626.83

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

2

Bath

12

Sleeps

$363.17

Beautiful renovated stately home, one of the original founder's homes of Three Oaks! Just around the corner from the Journeyman Distillery and all downtown Three Oaks has to offer! (5 minute walk to the heart of downtown Three Oaks)brbrAttic has been finished to add an additional 600 sq feet, featuring a bedroom, dressing room, living room with gas fireplace, ensuite bath with walk-in shower with rain shower head, large vanity. Attic is accessible through the upstairs bathroom, which has a private toilet closet. brbrAll bedrooms upstairs. Home offers beautiful designer furnishings, 3 comfortable king sized bedrooms and 1 queen, 3 large full bathrooms, (one upstairs with a marble shower, one downstairs with a tub/shower, attic ensuite with a rain shower), an attic living room with gas fireplace, a formal living room for cocktails and a spacious TV living room for cozy hangouts by the wood burning fireplace. Additional guests may sleep on the daybed in this room.brbrMarble updated kitchen features new appliances, a large washer and dryer, and granite countertops for easy cooking and entertaining. brbrThe large private yard, with backyard fully fenced in, features a large deck with outdoor sofa and chair, dining table and lush garden with firepit area and a gas grill await your stay.

Walk to Journeyman Renovated Spacious Victorian House, Beautiful Vintage Details

Three Oaks, Michigan, United States

4

Bed

2

Bath

9

Sleeps

$434.62

Welcome to our modern guest home on Youngren Road, a 2023 custom build nestled deep into twenty acres of private woods in Chikaming Township. Set well back from the road and surrounded by nothing but trees, this Harbor Country retreat feels like your own corner of the forest — with Cherry Beach on Lake Michigan less than a mile away.brbrThe open-concept living area is built around floor-to-ceiling windows that bring the woods right inside, making the landscape the centerpiece. A natural stone wood-burning fireplace runs floor to ceiling and makes it easy to settle in on cool evenings. The design is modern and clean with natural materials throughout. The main bedroom offers a queen bed while the second bedroom includes a bunk bed with additional trundle to sleep up to 3, offering an ideal set-up for families with children. brbrStep outside to a patio strung with lights, a charcoal grill for summer cookouts, and a firepit for the kind of evening you came to Harbor Country for. From here, walking trails wind through the surrounding twenty acres of woods — perfect for a morning hike or a quiet afternoon exploring with the kids.brbrWalk five minutes on foot to the paved walking and biking path along Red Arrow Highway that connects you north to Bridgman and south into New Buffalo, with coffee shops, craft breweries, and local restaurants all reachable without starting the car. Warren Dunes State Park, over twenty wineries and tasting rooms, the Journeyman Distillery, seasonal farmers markets, art galleries, boutique shopping, and live music at the Acorn Theater are all a short drive away.brbrModern, comfortable, and wrapped in nature — this is Harbor Country the way it's meant to be experienced.brbrA note about the property: our guest home is a separate structure but sits on the same wooded acreage as our family's home. You'll have your own entrance, patio, and outdoor space, and most guests never cross paths with us at all. On the rare occasion we're on the property during your stay, we're happy to point you toward our favorite local spots — or simply stay out of your way.brbrTraveling with another couple or family Our charming studio cottage sits just next door on the same wooded property, offering a separate private space with its own kitchen, patio, and easy walk to Cherry Beach. Ask us about booking both homes together.

Cottage

NEW Modern Wooded Retreat, Fireplace, Harbor Country, Close to Cherry Beach

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$215.83

UPDATESbrCLEANING brWe adhere to CDC guide lines for cleaning. Bleach and water to sterilize the toilet handle, faucets, stove knobs, door handles, light switches, backs of chairs. brBEACHESbrAll beaches that are open are New Buffalo, Warren, Weko and Silver, Harbert and Cherry . Cherry beach there is no more beach pass, $15 parking fee thank you Chikaming twnshp. First come first serve. You can enjoy the majestic sunsets.brbrbrJust a short 5 block walk to Harbert Beach. Located between Warren Dunes is a short drive 4 mi. Four Winds Casino is 10 mi. drive. Walk to the Swedish bakery/Luisa’s Cafe. Enjoy the wineries and breweries, walk the Galien River County Park, Cherry beach. Pick up your grilling needs at Falatics Meat Market [ online orders only https://www.falatics.com/ ] visit the many farmers markets all minutes away. Antique shops on Red Arrow. Cool off in the pool (not heated) or enjoy a fire in the evening (wood provided).

Cottage

Harbert Living a short drive to local attractions. Where fond memories are made.

Three Oaks, Michigan, United States