Vacation Rentals By Owner In Three Oaks, MI

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

$469.25

Summary:brbrWelcome to The Sycamore Suites Unit B, the 3-bedroom 2-bathroom unit located just steps from Journeyman Distillery and everything that beautiful Three Oaks, Michigan has to offer! This beautifully renovated unit has been thoughtfully updated with brand new kitchens & bathrooms so that you are your group can feel right at home.brbrbrbrThe Space:brbrAs you enter Unit B you will be welcomed into the dining area with a farmhouse style table that can seat 6. Next to the dining table is the 1st floor full bathroom as well as a bedroom that has a trundle bed. Right off the dining area is the newly remodeled kitchen that includes beautiful blue cabinets, quartz countertops, and brand new stainless steel appliances. Past the kitchen you will walk through French doors and be greeted into the large living space with a smart TV, large sectional, and lounge chair. Right outside of the living room is the screened-in back porch that has an outdoor dining table that seats 6. As you walk up the spiral staircase you will enter the 2nd floor hallway and the two bedroom doors. The primary bedroom to the left has a king-sized bed and has the 2nd bathroom located inside. The 3rd bedroom has a queen sized bed. brbrbrbrThe back yard features a porch that overlooks the fire pit area. Laundry is located in the basement.brbrbrbrGuest Access:brbrGuests have full-access of Unit B and the screened-in back porch. Please be respectful of the neighbors in Unit A. The back yard fire-pit area is a shared space.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:brbrThree 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 give guests access to Unit B which is located on the right side of the building and has 3-bedrooms and 2 bathrooms. The back deck that overlooks the fire-pit is a shared space. The unit includes an interior door that connects to Unit A, but it will remain locked and is not accessible during your stay. This door is only used when the entire home is booked as one unit.brbrbrbrInteraction with Guests:brbrHost is always available via call, text, or email to answer any questions or give area recommendations!

Apartment

6-Guest Apt Steps to Journeyman & Downtown 3 Oaks!

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

$364.14

Summary:brbrWelcome to The Sycamore Suites Unit A, the 2-bedroom 2-bathroom unit located just steps from Journeyman Distillery and everything that beautiful Three Oaks, Michigan has to offer! This beautifully renovated unit has been thoughtfully updated with brand new kitchens & bathrooms so that you are your group can feel right at home.brbrbrbrThe Space:brbrAs 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 property is divided into two unit - Unit A & Unit B. This Unit, Unit A, is located on the left side of the building and can be accessed with the unique smart lock code at the front porch.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:brbrThree 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 give guests access to Unit A which is located on the left side of the building and has 2-bedrooms and 1.5 bathrooms. The back deck that overlooks the fire-pit is a shared space. The unit includes an interior door that connects to Unit B, but it will remain locked and is not accessible during your stay. This door is only used when the entire home is booked as one unit.brbrbrbrInteraction with Guests:brbrHost is always available via call, text, or email to answer any questions or give area recommendations!

Apartment

4 Guest Apt Steps to Journeyman & Downtown 3 Oaks

Three Oaks, Michigan, United States

Bed

1

Bath

4

Sleeps

$918.68

5 Bedroom, 4 Bathrooms, Sleeps 12brbrDiscover the perfect Harbert escape, welcome to Sweet Cherry Pie. A beautifully updated and light-filled vacation rental designed for unforgettable getaways in Southwest Michigan. This spacious home features five comfortable bedrooms and four modern bathrooms, offering plenty of room for families, groups, and multi-generational stays. Large windows fill the interior with natural light, while the open-concept layout flows seamlessly from the stylish kitchen to the welcoming living area, complete with a cozy indoor fireplace—perfect for gathering after a day of exploration.brbrStep outside to enjoy one of the home’s standout features: a serene screened-in porch ideal for morning coffee, afternoon reading, or evening cocktails without the bother of bugs. This peaceful outdoor space adds to the home’s charm and provides the perfect setting to unwind and enjoy Harbert’s natural surroundings. Roast s'mores under the stars with your outdoor firepit. brbrLocated just minutes from the pristine shores of Cherry Beach, this vacation home puts you close to the area’s most beloved attractions. Spend your days swimming and sunbathing, then explore nearby New Buffalo, Union Pier, Sawyer, and Lakeside, all offering wineries, breweries, farm-to-table dining, boutique shopping, and scenic trails. The home’s central position in Harbor Country ensures you’re always near the best local experiences while still enjoying the privacy of a residential setting.brbrWith updated finishes, generous amenities, abundant natural light, and inviting indoor and outdoor living spaces, this property is perfect for travelers searching for Harbert vacation rentals, Southwest Michigan beach homes, and Cherry Beach getaways. Whether planning a weekend retreat or an extended stay, this Harbert haven invites you to relax, recharge, and experience the very best of Lake Michigan living.brbrAll the amenities you would expect in a quality rental including internet, central air/heat, washer/dryer, gas grill, outdoor firepit, wood burning fireplace, and much more!brbr**All Guests Required To Sign Our Guest Occupancy Agreement.brbr**Minimum Age of 30 Years Old To Rentbrbr**Maximum Five Car Parking

Gorgeous Harbert Home Close To Beach!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$805.06

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

$1075.9

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

10

Sleeps

$2456.33

Escape to W.S. Ranch a designer farmhouse on open prairie in Harbor Country, Michigan, with a heated pool, private spring-fed lake, and cabin loft. Sleeps 12 across multiple spaces, all yours exclusively.brbrbrTHE FARMHOUSEbrVaulted ceilings, reclaimed beams, and panoramic prairie windows set the tone. A stone fireplace anchors the great room; the chef's kitchen Thor range, oversized island was made for cooking with people you love. Bedrooms are dressed in organic linens with artisan touches. Baths are stocked with luxe towels and local bath products. Every detail is intentional.brTHE POOL HOUSE & CABIN LOFTbrA gravel path leads to the heated pool and cedar-lined pool house with kitchenette, full bath, and lounge, built for lazy afternoons and sunset cocktails. The separate cabin loft offers a private escape with workspace and warm natural light, ideal for teens, creatives, or anyone craving quiet.brTHE GROUNDSbrAcres of open prairie wrap a private spring-fed lake — swim, canoe, or fish as morning mist lifts off the water. Wander wildflower trails, stretch in the open field, or end the night around the fire pit under a sky full of stars.brAMENITIES AT A GLANCEbrbrHeated pool & cedar pool house with kitchenette + full bathbrPrivate spring-fed lake brCabin loft with sitting area & dedicated workspacebrChef's kitchen with Thor range & oversized islandbrBasketball court, yard games, fire pit & firewood (seasonal)brOrganic coffee, plush linens & artisan bath productsbrHigh-speed Wi-Fi, smart lock self check-in, washer/dryerbrEntire property to yourself — no shared spacesbrbrLOCATION — HARBOR COUNTRY, MIbrbrJourneyman Distillery — 5 minbrDablon Winery — 7 minbrWarren Dunes State Park — 10 minbrNew Buffalo & Three Oaks — 10–12 minbrChicago — ~90 minbrbrTHE EXPERIENCEbrW.S. Ranch is luxury with soul. You'll sip wine poolside, cook with family in a real kitchen, and fall asleep to prairie silence. This isn't a rental it's a feeling. Cedar and woodsmoke. Prairie wind. Honest design. The Midwest at its finest.brYour entire private retreat awaits.

Country House

W.S. Ranch Luxe Farmhouse · Heated Pool · Private Lake · Camp Loft

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$362.33

Newly renovated 1920's Bungalow loaded with character. Spacious interior with a mix of modern and vintage furnishings that will leave you relaxed and rested. Large private backyard with grill and firepit to enjoy starry Three Oaks nights. brbrOnly 4 blocks from Journeyman Distillery and close to all of the restaurants and shops in downtown. Perfect place to stay for a wedding or getaway visit near wineries, breweries and beaches. Come see the village that everyone is talking about!brbrOur space : Our home is updated throughout with refinished original woodwork highlighting the space and premium furnishings that will ensure you are comfortable throughout your stay. BRAND NEW kitchen with commercial style range and black stainless steel appliances add a modern look. New flooring, bathrooms and beds plus tons of amenities make this the premiere destination for your trip to Three Oaks.

The Heartwood House<3 : Dwntwn Three Oaks, 2BR/2BA

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$456.25

Escape to Harbor Country, where charm meets comfort in this luxurious pet-friendly 3BR/2BA retreat. Bright living room, chic kitchen, comfy king & queen bedrooms. Sip wine by the fire pit, soak under the stars in the hot tub, or linger on the delightful screened porch. Just minutes from Lake Michigan beaches, cafés, and shops, it’s a perfect haven for romance, family time, and unforgettable memories.brbrThe spacebrWelcome to Good Karma Guesthouse, all good vibes here!brbr3 year new interiors with gorgeous wood floors throughout, loads of natural light, and elegant yet homey furnishings. Relax to your heart’s content in the chic and comfy living room with its plush couch, big picture windows, decorative fireplace, and Smart TV. The kitchen has modern appliances, quartz countertops, and everything you need to prepare wonderful meals. Screened porch, deck, grill, hot tub, fire pit.brbrYou’re within walking distance to downtown Three Oaks with excellent restaurants, bakeries, boutiques, parks, a farmers market, and more. Enjoy extra-special spots like Acorn Theater, Journeyman Distillery, Dyer's Meat Market, Vicker's Theater, Froehlich's Bakery, Alan Ray's Coffee, Patellie's Pizza, The Bottle Shop, Long Story, Oaks Eatery, Viola Cafe, Tom Cat Tavern, and more!brbrAll of the bedrooms feature top-quality bedding and linens, ensuring a sound sleep and sweet dreams for you and all your guests. Good Karma Guesthouse can sleep up to 6.brbrMAIN FLOORbrBedroom 1: 1 Queen bedbrbrUPPER LEVELbrBedroom 2: 1 King bedbrBedroom 3: 1 Queen bedbrbrStep outside to a beautiful screened-in porch that opens onto a large wrap-around deck with a natural gas grill, leading to a private 6-person hot tub, yard, fire pit, and plenty of parking. There’s also a spacious front porch with lounge chairs for relaxing at sunset. The sunsets are not to be missed!brbrOur guests have also 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.brbrBeing a historic town, Three Oaks also has the Vickers Theater, a showcase for nearly a century of high-quality cinema. Another advantage of staying at Good Karma Guesthouse is its proximity to the popular restaurants, galleries, and boutique shops of downtown New Buffalo, as well as the majestic, crystal-sand Lake Michigan beaches! You can also enjoy many activities from being a short drive away from the region’s largest recreational harbor – including boat and other watercraft rentals, fishing expeditions, day or evening cruises, and various woodland, lake, and riverside parks with hiking and biking trails galore.brbrLest we forget, 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 enjoy visiting New Buffalo’s Oselka Park, which has baseball fields, playground equipment, and tennis courts. For even more variety, nearby Union Pier also has great restaurants, coffee shops, and breakfast spots. Plus, being centrally located, there are plenty of fun activities to keep you busy during your vacation, including:brbrLocal wineriesbrArt galleriesbrAntique shopsbrGolf coursesbrYou pick farmsbr…and more!brbrOther things to notebrbrThe minimum age to rent this home is 25.brbrWe welcome up to 2 dogs not exceeding 40lb each for $100. Please include the number of pets you plan at booking.brbrA non-refundable Accidental Damage Waiver is included with your reservation. This waiver covers accidental damage or loss to the rental property caused by you or members of your party, up to a maximum of $2,000. This plan does not cover intentional acts, gross negligence, or wilful misconduct.brbrOut of respect for our cleaners and their families, we do not permit check-ins or check-outs on Thanksgiving Day and Christmas Day. Thank you for your understanding.brbrOther things to notebrOur Reviews!brbrMollybrbrRating, 5 starsbrAugust 2025brLovely long weekend this summer -2 adults, 3 kids. Beautifully appointed home, really fun outdoor area. Responsive hosts and very clean home. Close to everything in Three Oaks and only about 12 minutes away from New Buffalo. Highly recommend!brbrAndrewbrRating, 5 starsbrJuly 2025brPerfect spot for a summer vacation rental with a short drive to Lake Michigan beaches. Family friendly, pet friendly. Good for hosting others that were staying near us for a nice small patio dinner and some s’mores by the fire after!brbrJenniferbrRating, 5 starsbrMarch 2025brThis is a lovely home in Three Oaks. It was very clean with beautiful decor. In walking distance to everything Three Oaks has to offer. The hot tub and screened in porch were an added bonus. Definitely don't hesitate to rent this house.brbrJamesbrRating, 5 starsbrMarch 2025brWe really enjoyed our weekend stay! The home is very clean and has a great set up allowing you room to enjoy the inside and outside of the house. The kitchen is well stocked with anything you need to cook your own meals. There were so many thoughtful details provided for the humans and my dog. The location is walking distance to great shops and restaurants in Three Oaks and is centrally located to many other great shops and restaurants in Harbor Country. Would love to stay here again and highly recommend!

Charming Home with Hot tub & walk to town!

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$668.0

**** Enjoy the winterscape outside while siting beside a fire with a cup of hot chocolate. Pool and hot tub are closed and not available for use until mid-May 2026.****brbr** Minimum age requirement of 30 years old to rentbr**Events, parties, or large gatherings are strictly prohibited and could incur fines by local municipalities or removal from propertybr**No smokingbr**Maximum car parking is 4brbr- Heated pool hot tub open from Memorial Day weekend to Labor Day weekendbrbrTucked away on a country road between Harbert and Three Oaks is a home designed for relaxation: Third Coast Ranch. The three bedroom home, surrounded by trees, features an in-ground heated pool, hot tub, a small pond and gorgeous gardens. brbrRelax any time on the screened porch with ceiling fan, perfect for a rainy night. The dining table can seat 12 and the kitchen is large enough for several cooks at once. Roku TV with popular apps, fast WiFi, and extensive DVD collection. brbrOur quiet country roads and nearby trails are perfect for long walks or bike rides, surrounded by woods. brbrFast Comcast Business WiFi with Google mesh makes it easy for everyone to use their devices. brbrTwo fireplaces are anchored at each end of the home, one in the kitchen and the other in the primary bedroom. The primary bedroom boasts a king size bed, ensuite full bath and wood burning fireplace. Bedroom 2 has bunk beds (twin over full) and a trundle perfect for 3 or 4 children. Bedroom 1 features a queen size bed and TV. br brThe home is one mile from Cherry Beach (with parking lot) and a short drive to antiques, wineries, breweries, farm stands and charming restaurants. This home is the ideal location for a family getaway, weekends away with friends or couples vacation. brbrThe pool and hot tub are open seasonally. The chef's kitchen is stocked with everything you need. A private setting means you'll rarely run into neighbors.

Charming 3-bedroom house with a pool and spa on 5 acres of woods near Harbert.

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$1643.43

About this spacebrFeaturing a Private 86 degree pool with a security cover, 101 degree hot tub, outdoor shower and fenced back yard for fido your going to enjoy your house time as much as your beach time!br5 bedrooms offer sleeping accomodations for 6 adults and 6 children (or 2 adults each in a twin bed). 2 ensuite kind bedrooms and the 3rd with a half bath and full bathroom just down the hall.brGuest accessbr100% of the property

Cherry Beach Pool House

Three Oaks, Michigan, United States

5

Bed

Bath

11

Sleeps

$204.51

Summary:brbrThe NookbrbrbrbrThe Space:brbrLocated steps from downtown Three Oaks, this charming vacation home is ready to provide your group with a cozy getaway by Lake Michigan. Light and bright, this home offers the perfect layout with all the comforts of home. Sip your morning coffee on the covered front porch before heading out for a day of fun. You'll love the home's fun decor, comfortable furniture, and glossy floors, especially while you catch up with old friends in the living room. You can whip up delicious dishes in the sparkling kitchenette, with stainless steel appliances and many handy extras. Gather for drinks, meals, and good conversation in the open living/dining area. A private washer/dryer and free WiFi add convenience to your stay. When evening falls, gather everyone around the outdoor firepit for toasted s'mores before getting a long and luxurious sleep in one of the home's well-appointed bedrooms. bTHINGS TO KNOW/b There is a cabinet-style fridge and freezer.

Quaint, budget-friendly home walking distance to town with grill - dog-friendly

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$426.73

Summary:brbrThree Oaks EscapebrbrbrbrThe Space:brbrEscape to this charming family retreat halfway between Three Oaks and Sawyer. Offering a peaceful getaway with easy access to Lake Michigan attractions. Located a mere 5 miles from Warren Dunes State Park, you can enjoy sandy shores and stunning sunsets just a short drive away. Within the city limits of Three Oaks, you'll discover art galleries, restaurants, bakeries, and unique shops, including a National Historic Site butcher shop and a distillery. The Acorn and Vickers theatres provide entertainment options, ensuring there's something for everyone to enjoy. Additionally, wineries, breweries, and more beaches are all within easy reach of this centrally located home. This elegant house boasts a large three-season room, perfect for enjoying your morning coffee. Head outside down to the lower patio in the evening to host a barbecue with friends and family. The outdoor fire pit sets the scene for cozy evenings under the stars. With ample outdoor spaces, you'll be able to enjoy nature at all times. The well-appointed interior features four queen beds, and three separate living areas, each equipped with their own TV for family and guests to enjoy their own comfortable space. Amenities such as a dedicated work-from-home office, washer/dryer, central AC, internet, and a fully equipped kitchen ensure a comfortable stay. Whether you're relaxing on the patio, exploring the local attractions, or unwinding in the cozy living room, this home offers the perfect blend of comfort and convenience. Book your stay at this elegant family retreat in Three Oaks today and experience the best of Lake Michigan living in a bright and open setting. LAKE MICHIGAN (4.4 miles): Hiking, wildlife viewing, sightseeing, biking, boating, swimming, beaches THINGS TO DO: Chikaming Township Park & Preserve (2.7 miles), Downtown Sawyer (3.2 miles), Downtown Three Oaks (3.6 miles), Captain Mike‚Äôs Fun Park (6.6 miles), Downtown New Buffalo (8.9 miles), Downtown St. Joseph (20.2 miles), Silver Beach (21.7 miles), University of Notre Dame (32 miles) MUSEUMS: The Region of Three Oaks Museum (3.5 miles), New Buffalo Railroad Museum (9.2 miles), Hesston Steam Museum (10.2 miles), Old Lighthouse Museum (19.2 miles), Curious Kids‚Äô Museum (21.0 miles), The History Museum (31.4 miles) PARKS & BEACHES: Warren Woods State Park (2.3 miles), Harbert Community Park (3.4 miles), Cherry Beach (4.3 miles), Warren Dunes State Park and Beach (5.7 miles), Galien River County Park (7.2 miles), New Buffalo Beach (9.5 miles), Grand Mere State Park (13.9 miles), Indiana Dunes National Park (31.9 miles) OUTDOOR ACTIVITIES: Kesling Nature Preserve (8.0 miles), Weko Beach (8.8 miles), Spicer Lake Nature Preserve (11.1 miles), Friendship Botanic Gardens (17.0 miles) AIRPORTS: South Bend International Airport (28.5 miles), Chicago Midway International Airport (82.8 miles), O'Hare International Airport (93.0 miles)

Serene Home with Fire pit, Gas Grill, WIFI & Close to Beach

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$399.58

Summary:brbrThree Oaks RetreatbrbrbrbrThe Space: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. The 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. Downstairs, 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! The 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. Things to Know Free WiFi 1 dog welcome For an additional sleeping option, there‚Äôs a queensofa bed in the living room Please adhere to our 'Good Neighbor' policy; No Parties; Quiet Hours enforced This property is managed by Vacasa Michigan LLC

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

Three Oaks, Michigan, United States

Bed

Bath

Sleeps

$185.95

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

$1450.4

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

6

Bed