Vacation Home Rentals By Owner In Three Oaks, MI

$330.36

You're in a hot tub; you see gardens and hear wind blowing through the pines.

Three Oaks, Michigan, United States

Really a unique place! You really feel like you're way out in the country.brWalk down to the river, skip stones on the pond, sit and listen to the birds. Fantastic fireplace, a great kitchen. brWe have 2 bedrooms. The Master bedroom has a Queen size bed and a sofa bed, the Library has a trundle bed with 2 twin beds that can connect or not. In the living room there is a sofa bed that bends back to become a full bed. We also have a few Queen size raised air beds to set up in a large tent or on the porch. brFor more than 4 guests, the price is $50/ night for each extra guest. 8 guests are a full house!brbrWe love dogs, and have had guests brings their dogs for the last 9 years. brBut the house always gets torn up, screens ripped, etc. brIf you want to stay, and have a dog, and you can assure me that your dog won't bark all the time and be quiet, and does not shed, let's talk about it. brbrSome of the time I stay in my vintage RV at the other end of the property. I value my guests' privacy, so you will not see or hear me, unless you need me! My iPhone is the front desk!

2

Bed

2

Bath

10

Sleeps

$437.32

/ Nightly

Private Vacation Home

Walk to Journeyman Renovated Spacious Victorian House, Beautiful Vintage Details

Three Oaks, Michigan, United States

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.

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$473.42

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Private Vacation Home

The Sycamore Cottage - 2 BR & 1.5 Bath - Hot Tub - Steps to Downtown

Three Oaks, Michigan, United States

The Sycamore Cottage is a 2 bedroom 1.5 bathroom one story single family home. The single floor design hosts two queen size bedrooms, an open layout kitchen, dining, and living room along with 1.5 bathrooms complete with laundry for your use. Private Hot Tub included!brbrExplore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Sycamore Cottage. A few minutes walk to charming shops, restaurants, and event venues including Journeyman Distillery, The Acorn Theater, and The Social Club in Three Oaks. Three Oaks is just a ten minute drive from the beautiful beaches of Lake Michigan and thirty-five minutes to Notre Dame. Enjoy the small town lifestyle and find your own moment to getaway.

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$666.74

/ Nightly

Private Vacation Home

The Hickory House - Walk to Downtown Three Oaks - Week Stay Discount

Three Oaks, Michigan, United States

Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, The Hickory House. Less than 5 minute walk to charming shops, restaurants, and event venues including Journeyman Distillery, The Acorn Theater, and The Social Club in Three Oaks. Three Oaks is just a ten minute drive from the beautiful beaches of Lake Michigan and thirty-five minutes to Notre Dame. Enjoy the small town lifestyle and find your own moment to getaway.

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$2308.03

/ Nightly

Private Vacation Home

Luxury Retreat for 26, Pool, Hot Tub, amazing!

Three Oaks, Michigan, United States

Welcome to Dogwood, a luxurious farmhouse with a heated pool and hot tub near Lake Michigan. The main house offers 5 bedrooms, a chef’s kitchen, and spacious living areas, the guest house adds 2 more bedrooms ! Enjoy the fire pit, outdoor dining, and wooded setting perfect for family reunions, retreats and more! Spend sunny afternoons by the pool, grill dinner on the deck, or head to the beach. With space for everyone, Dogwood is the perfect place for your next large group getaway!

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$445.5

/ Nightly

Private Vacation Home

Renovated Victorian Home with Private Garden & Fire Pit!

Three Oaks, Michigan, United States

About this spacebrTucked away on a vast 8442 sq. ft. lot, this revamped 3-bed Colonial style house is your perfect hideaway, situated walking distance to Three Oaks town center! Within minutes you can dine at slew of restaurants, stroll through picturesque parks, and attend the historical Vickers Theatre! Upon returning, head to the fenced backyard for a BBQ cookout or marshmallow roasting by the firepit, or retreat indoors to the 1800 sq. ft. interior, featuring HDTVs in each bedroom and speedy 500 Mbps Wi-Fi!brbrGet ready to enjoy the quaint and peaceful vibes of our multi-story abode, where the timeless charm of our 100-year-old home meets modern polish in every lovingly restored detail. brbrIdeal for family gatherings or large groups, our home invites you into its two charming living rooms, each brimming with a stylish vintage allure. Sink into the plush sectional couch, pull out the sofa bed if needed, and enjoy a film on the 58” smart HDTV, creating a perfect setting for memorable, cozy movie nights.brbrOnce you’ve tucked away your luggage, it’s time to let loose and celebrate. Elevate your experience and step out onto your private backyard, an excellent spot to crack open a bottle of bubbly and make a toast to a well-deserved escape from the daily grind. brbrFeel the excitement build up as you uncover a variety of premier amenities and thrilling pursuits at the property and the surrounding area making our home an ideal launchpad for families seeking a laid-back getaway:brbrAT THE PROPERTY:brbr✓ Start your day off with a steaming cup of joe made from our complementary Keurig coffee maker.brbr✓ Crank up the beats and groove to your favorite tunes through our Bluetooth speaker.brbr✓ Fire up the BBQ grill, cook up some sizzling steaks and enjoy your meal amidst outdoor seating for a delightful alfresco dining experience.br br✓ Let your pets explore the freedom of a fenced backyard, dotted with a grassy lawn and a beautiful floral garden, while you lounge in comfort on a cushioned chair in the veranda. brbr✓ After a hearty family dinner, transform the dining table into a battleground of fun with our diverse selection of board games for some friendly post-meal competition.brbrOUTSIDE THE PROPERTYbrbr✓ Looking for a change of scenery Take a leisurely 10-minute walk to Three Oaks Spokes Bicycle Club, rent a bike, and set off to explore the picturesque trails at places like Chikaming Township Park & Preserve.brbr✓ For some prime-time entertainment, take a short walk to downtown and visit the Acorn – a vibrant arts venue set in a historical featherbone factory, offering a diverse array of performances including music across genres like rock, folk, indie, and jazz, as well as drama, comedy, and open mic nights.brbr✓ Craving a nature escape In just 10 minutes, you can explore over 2,500 acres of breathtaking landscapes. Make your way to the sandy shores of New Buffalo Beach, the picturesque trails of Spicer Lake Nature Preserve, the lush greenery of Warren Woods State Park, and the majestic dunes of Warren Dunes State Park!brbrKitchen and Local RestaurantsbrbrAs your appetite begins to stir, make your way towards our open plan kitchen, characterized by its overhead white cabinets and top-notch appliances. Whether you're an experienced cook or a beginner in the kitchen, you'll discover all the essentials to prepare breakfast, lunch, or dinner using our:brbr• Full size refrigeratorbr• Microwave, oven and stovebr• Cutting board and gourmet knife setbr• Pots and pansbr• Oil, salt and pepperbr• Toasterbr• Blender br• Dish soap and hand soapbr• Plates, bowls, mugs, glasses, and silverwarebr• Dishwasher with dishwashing tablets for quick and easy clean upbrbrDon’t feel like cooking No problem! Treat your tastebuds to a slew of international and local cuisines – all within a 10-15-minute walk or drive from our doorstep, including:brbr• Brunch and Vegan (Oaks Eatery)br• Bakery and breakfast café (Froehlich's Kitchen & Pantry)br• Pizza (Patellie's)br• Hand crafted cocktails (Staymaker Restaurant at Journeyman Distillery)br• Italian (Brewster's New Buffalo)br• Chinese & Japanese (Song Asian Cuisine)br• Classic American with Rooftop Bar (The Stray Dog Bar & Grill)br• Mexican (RIOS MEXICAN GRILL #1)brbrBedroom and BathroomsbrbrWhen it’s time to hit the hay, swing open the door to one of our 3 bedrooms and get ready to be charmed. Picture this: a spacious room bathed in soft, inviting light, soft carpeting underneath, and oh-so-cozy bedding that practically beckons you to jump right in.brbr It's more than just a room - it's your own slice of comfort heaven. A total of 6 guests can fall asleep comfortably here, and feature:brbrBedroom 1:brbr• King size mattressbr• Chest of drawersbr• Ceiling fanbr• 32” smart HDTVbrbrBedroom 2:brbr• 2 full size mattressesbr• Chest of drawersbr• 1 nightstand with a lampbr• Ceiling fanbr• 32” smart HDTVbrbrBedroom 3:brbr• King size mattressbr• 1 nightstandbr• Chest of drawersbr• 32” smart HDTVbrbrOur immaculate bathrooms continue the theme, beautifully outfitted gleaming with sink vanities, a bathtub and shower, and all the essentials you need to ensure you emerge refreshed and ready to take on the day:brbr• Hair dryerbr• Shampoo & conditionerbr• Fresh bath towelsbr• Starter pack of toilet paperbr• Hand soap

3

Bed

2

Bath

8

Sleeps

$423.27

/ Nightly

Private Vacation Home

Three Oaks Creek House -- Perfect -- NEW HOT TUB! 3BR +king bed in screenhouse

Three Oaks, Michigan, United States

Contemporary house on Spring Creek—a spawning waterway. brbr3 BR, 2ba, basement rec room, brand new hot tub on attached deck and spectacular architectural screenhouse (4th bedroom) at water's edge. brbrOpen floor plan, stone fireplace, gourmet kitchen and 4000 CDs for spontaneous entertaining. brbrMaster Bedroom: br-Tempur-Pedic king mattress and modern steel bed frame; br-Gladiator cabinets, drawers and butcherblock surface, 8' mirrored closet with Elfa shelving to store all your clothes and other supplies;br-Large glass desk with retro office chair, computer monitor, printer, office supplies. br-Sliding door to back deck.brbrSecond bedroom has queen bed, standing desk, lots of surfaces for unpacking your clothes and other items. brbrThird bedroom has small desk, built-in shelving and en suite, pink bathroom. brbrMain bathroom has huge Jacuzzi tub, custom tile and one-of-a kind artisan counters and is located next to first two bedrooms.brbrSkylighted kitchen is 100% ready for cooking everything and other entertaining: New fridge, oven, washer, dryer, custom blinds. Kitchen and pantry are filled with upscale cookware, bakeware and a variety of serving ware. You do not have to bring anything to this kitchen -- it is all there. brbrPendant lights over breakfast counter made of solid cherry from local artisan. Corian counters and designer cabinets with under cabinet LED lighting. Pantry has beautifully restored vintage metal cabinets and serving cart with even more pots, pans, bowls, glassware -- and room to put away the food you buy.brbrDining/Music Room has table with two leaves to seat 4-10 people, beautiful grand piano, component stereo plus DJ mixing panel, 4000 CDs on custom built shelving, retro couch, over sized leather chair, 1940's lamps on 1950's side tables, and two beautifully upholstered swivel club chairs.brbrLiving room has European leather sectional, Stickley chair and ottoman, marble tables, stone fireplace, large TV, oversized day bed, green vintage Formica table and chairs, vaulted ceiling, 5 gigantic picture windows, 8 sliding windows and three windows at the top that open with remote, bringing in fresh air from all four directions, plus the sounds and smells of the woods and creek. LR also has a sliding door onto the back deck. Four bird feeders right at the windows showcase dozens of species of colorful birds. brbrSlate pool table, jukebox with 100 carefully selected 45 RPM records, retro couch, cocktail table and single bed in basement game room. Third toilet, newer washer/dryer and custom stainless steel sink in adjacent laundry room.brbrCurated art collection from around the world throughout the house. brbrCupboards with 125 board games for family fun, and books galore.brbrWi-fi throughout, Roku connected DTV. brbrWell water, rich in minerals. Very healthy for bathing. Safe to drink, but filtered water also available. House is professionally cleaned but located in the woods. Don't expect hotel clean everything.brbrOutdoor space: Three and a half Acres, Architectural screen house on attached deck. Outdoor grill and seating areas. Yards and gardens. Woods and field. Concrete tennis court and basketball hoop. Big view -- see where the glacier stopped. Long wooded driveway.brbrCharming, vibrant, downtown Three Oaks (1.5 miles), the arts and cultural center of Harbor Country, features restaurants, galleries, an amazing live performance space, a charmingly restored movie theater, parks with live summer entertainment and shops offering antiques and vintage treasures, clothing, bike rentals, wine and spirits and more. brLake Michigan beaches (7 miles). 30 minutes from UND. 75 minutes from Chicago.brIn-area options include winery tours, botanical gardens, miles and miles of hiking and biking trails, river kayaking, golf courses, summer farmers' markets and so much more!

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$678.4

/ Nightly

Private Vacation Home

Four Seasons Retreat

Three Oaks, Michigan, United States

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

3

Bed

2

Bath

6

Sleeps

$1290.83

/ Nightly

Private Vacation Home

Three Oaks Stunner With Private Pool & Hot Tub!

Three Oaks, Michigan, United States

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

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$1025.0

/ Nightly

Private Vacation Home

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

Three Oaks, Michigan, United States

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

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$1027.45

/ Nightly

Private Vacation Home

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

Three Oaks, Michigan, United States

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

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$297.99

/ Nightly

Private Vacation Home

Backyard Oasis w Downtown Walkability, Fire Pit

Three Oaks, Michigan, United States

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

2

Bed

1

Bath

6

Sleeps

$398.33

/ Nightly

Private Vacation Home

Newly updated wooded retreat near Three Oaks and Union Pier

Three Oaks, Michigan, United States

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

4

Bed

2

Bath

10

Sleeps

$1572.47

/ Nightly

Private Vacation Home

Gorgeous Estate With Pool, Hot Tub, and MORE!

Three Oaks, Michigan, United States

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

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Bath

Sleeps

$1051.17

/ Nightly

Private Vacation Home

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

Three Oaks, Michigan, United States

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*

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Bath

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$649.25

/ Nightly

Private Vacation Home

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

Three Oaks, Michigan, United States

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

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Bath

Sleeps

$393.71

/ Nightly

Private Vacation Home

Cottage In The Heart Of Harbor Country - Steps From Town

Three Oaks, Michigan, United States

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

3

Bed

2

Bath

10

Sleeps

$1477.43

/ Nightly

Private Vacation Home

35-Acre Retreat | Pool, Pickleball & Private Woods

Three Oaks, Michigan, United States

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

6

Bed

6

Bath

17

Sleeps

$1300.0

/ Nightly

Private Vacation Home

The Modern Oak Lux Getaway Steps from Journeyman

Three Oaks, Michigan, United States

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

4

Bed

4

Bath

10

Sleeps

$1104.07

/ Nightly

Private Vacation Home

Cozy Haven Near Lake Michigan Beaches on 2 Acres

Three Oaks, Michigan, United States

Summary:brbrSet on 2 acres in Three Oaks, Cozy Haven offers a more refined Southwest Michigan stay near Cherry Beach, Gordon Beach, and Pier Road Public Beach. The setting feels private, the interiors are beautifully updated, and the layout suits weekends with friends, family beach trips, and longer stays alike. Time here can shift easily from the shoreline to dinner at the house, with a pergola for evening hours outside and a dedicated workspace that adds flexibility for longer visits.brbrbrbrThe Space:brbrInside, the house has a fresh, polished look. Sliding glass doors open the main living area to the deck with outdoor dining seating, and the fireplace gives the living room a serene ambiance after dark. The kitchen sits at the center of the house with white cabinetry, stainless appliances, open shelving, and a large island with seating. Just beyond it, the dining area faces the property through wide windows, keeping the setting in view throughout the day.brbrbrbrThe bedroom layout suits a full group well. The primary suite includes a California king bed, a large ensuite bath, and direct access outside. Another bedroom has a king bed, while a third offers a queen. The bunk room includes two twin bunk beds. In the fifth bedroom, a daybed and dedicated workspace make it easier to extend the stay without losing time to email or a call.brbrbrbrMaster Bedroom: California King BedbrbrBedroom 2: King BedbrbrBedroom 3: Queen BedbrbrBedroom 4: 2 Single Bunk BedsbrbrBedroom 5: Day Bed (single) with dedicated workspacebrbrbrbrThe bathrooms continue the updated finish found throughout the house. The primary bath includes a soaking tub and double vanity, while the additional baths are finished with walk-in showers and a clean, polished look. A separate laundry room with washer and dryer is also available for guest use.brbrbrbrOutside, the front pergola creates an inviting place to settle in after the beach, the back deck is an awesome spot for casual dining, and the large yard adds to the sense of privacy across the property. With 2 acres to enjoy, the setting feels calm and removed, even with some of the area’s best public beaches just minutes away.brbrbrbrLocated in the heart of Harbor Country, Cozy Haven places you close to everything Southwest Michigan has to offer. Spend your days relaxing on nearby Lake Michigan beaches like Cherry Beach, Gordon Beach, and Pier Road Public Beach, exploring the shops, galleries, and restaurants of Three Oaks, and visiting local wineries, breweries, and distilleries. Enjoy farmers markets, antique shopping, biking scenic backroads, hiking nature trails, golfing, and seasonal events plus easy access to Union Pier, New Buffalo, and Sawyer for even more to explore.brbrbrbrOther Things to Note:brbrTo ensure a safe and compliant stay, all guests are required to complete identity verification prior to check-in. A valid government-issued photo ID will be collected and verified, and the name on the ID must match the credit card used for payment. When applicable, a background screening may also be required as part of the booking process.brbrbrbrAll guests are required to review and sign Juniper Holiday + Home's Guest Occupancy Agreement prior to check-in. While we understand that events can affect your trip, it is our policy to stick to the agreed-upon cancellation policy in the listing. We recommend purchasing vacation travel insurance if you suspect you may need to cancel your reservation.brbrbrbrThe minimum age to rent this home is 25.brbrbrbrWe welcome up to 2 dogs at this home at no additional charge. Please include the number of pets you plan to bring or let our team know after booking. brbrbrbrParking is available in the driveway for up to four vehicles. The barn and garage are not accessible to guests.brbrbrbrOut of respect for our staff and their families, we do not permit check-ins or check-outs on Thanksgiving Day and Christmas Day. Thank you for your understanding.brbrbrbrPermit No: STR-25-0377

5

Bed

3

Bath

10

Sleeps

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