Places to stay in Three Oaks

4.97 out of 5 average rating, 177 reviews

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

4.93 out of 5 average rating, 151 reviews

An inviting kitchen and dining area is highlighted by a long wooden table surrounded by a mix of chairs. Natural light fills the space through large windows, illuminating the white walls and beamed ceiling. A cozy living area is visible in the background, featuring a fireplace.

Cottage in Three Oaks

The Happy Cozy-Pets Welcome, Fire Pit, Privacy

If relaxing in nature in a calm and cozy home is what you're seeking, you'll find it here! It's been designed to make you feel at peace and comfortable inside while providing several outdoor spaces for you to enjoy the sights, sounds, and smells of nature. The open floor plan and large dining table create a grand gathering space for everybody to be together and create the memories that matter most. Feel free to safely start a campfire outside or in the fireplace indoors. It's all here for you!

Superhost

The open dining area showcases a large table with a decorative runner, surrounded by wooden chairs. A blue accent wall provides a bold backdrop, while a wall clock and lamp add functional decor. Natural light fills the space, highlighting the inviting layout.

4.89 out of 5 average rating, 105 reviews

The Lucky Charm House -Walk to it all! Cute, cute

Cute as can be, super comfy, 3 blocks to downtown 3 Oaks. Walk to Acorn Theatre, Journeyman & shopping in an eclectic quintessential small town 90 mins from Chgo. Hike local trails, beach it up at Warren Dunes State Pk, bike ride country roads -Explore Harbor Country. Wonderful dining, brew pubs and wineries to explore. Open living space w/large DR. Primary BR +bth w/shower. 2nd BR w/full bed +single bunk. Large back porch +fenced yard. 2 large TV’s, Wifi/cable. Daybed front porch.

A natural landscape features rolling sand dunes bordered by a lake. Sparse trees and grasses provide greenery against the sandy terrain. Individuals are seen walking along the dune, with the calm water visible in the background, enhancing the serene atmosphere of the scene.

4.98 out of 5 average rating, 141 reviews

1 Block to Journeyman - Dog Friendly/Patio/Firepit

Our newly built (2022) home is located just 1 block to Journeyman Distillery and the quaint downtown of 3 Oaks. Our home has been thoughtfully designed to create a serene and memorable stay for our guests. Eclectic shops, restaurants, and galleries are a short walk away. Drive to local beaches in less than 15 minutes. Spend your day exploring Harbor Country - wineries, breweries, hiking, biking, golf, beaches, blueberry picking, antiquing, and so much more. 3 Oaks is at the center of it all!

Tiny home in New Carlisle

A charming cabin exterior is highlighted with warm wood tones and soft string lights. A small porch features a bench and decorative potted plants, while the surrounding green grass creates an inviting outdoor space. The sky reflects a soft twilight hue.

4.99 out of 5 average rating, 155 reviews

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country

Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

A spacious outdoor area is surrounded by lush greenery, featuring a wooden deck with seating. A fire pit area is visible, along with a gravel path leading through the landscaped space. Trees provide shade, enhancing the serene environment.

4.99 out of 5 average rating, 104 reviews

2 blocks to Journeyman, 12 mins to Beach, King Bed

Highlights: ✔ Designer rehab in 2022 ✔ Sleeps 8 ✔ Outdoor firepit ✔ Relaxing back porch ✔ 5 min walk to Journeyman ✔ Easy 5-10 min walk to Three Oaks dining + shopping ✔ 8 min to wine tastings ✔ 10 min to New Buffalo, Union Pier, Sawyer ✔ 12 min to beach ✔ Gas BBQ grill ✔ Smart TVs & board games ✔ King bed in main bedroom ✔ Fabulous front foyer for wedding photos ✔ EV charger ✔ Luxury custom-designed home ✔ 3 vehicle parking ✔ Computer workstation ✔ High speed wifi ✔ Fully stocked

4.96 out of 5 average rating, 136 reviews

The Heartwood House<3 : DT Three Oaks w/Game Room

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. Only 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 near wineries, breweries and beaches. Come see the village that everyone is talking about!

4.88 out of 5 average rating, 104 reviews

Two white Adirondack chairs are positioned adjacent to a circular fire pit. The ground is covered with colorful fallen leaves, and trees with yellow foliage provide a natural backdrop. The scene reflects a serene outdoor space ideal for relaxation.

Apartment in Sawyer

Morton's Retreat Cozy 1 Bedroom Apartment

Cozy comfort close to Michigan's most popular state park, breweries, wineries, antique malls and farm-to-table restaurants. Morton's Retreat has plenty of room to relax. Charcoal grill and fire pit (shared with Morton’s other retreat) for use in a spacious yard. Private entrance with keyless entry makes check-in a breeze. One other Airbnb located next door in same building. Two complimentary local beers, seltzer water and a snack are provided to help kick off your stay.

4.98 out of 5 average rating, 109 reviews

A framed wall art piece is displayed, featuring the phrase 'this must be the place' in a mix of grey and navy letters. The art is set on a white background and mounted on a light-colored wall.

Apartment in Three Oaks

2 BD Apt Downtown, 1 Block to Journeyman & Acorn

The Sycamore Street Apartment is a thoughtfully designed space in the heart of Three Oaks, MI. This apartment is on a quiet, tree lined street just one block from Journeyman Distillery, the Acorn Theater, and the quaint shops & restaurants lining downtown Three Oaks. Enjoy small town charm while being minutes from the beaches along Lake Michigan, Warren Dunes State Park, wineries, antiquing and all that Harbor Country has to offer. We look forward to welcoming you!

A screened-in porch features a couch with striped cushions and a green lounge chair, providing comfortable seating options. Light wooden flooring enhances the inviting space, while large windows allow for ample natural light and views of the backyard.

4.99 out of 5 average rating, 145 reviews

Dog Friendly Downtown Three Oaks Cottage! Fenced!

Just a short walk to charming downtown Three Oaks, home of the famous Journeyman’s Distillery and all the shops and eateries Three Oaks has to offer. It is also a quick drive to the beautiful beaches at Warren Dunes State Park and New Buffalo. This cheerful home has queen beds and a fully stocked kitchen. Plus a huge fenced-in back yard, so bring the kids or the dogs and know they are safe while you relax in the three-season room or on the outdoor deck!

A coffee table is featured in a well-lit living room, displaying a stack of travel and design books. A glass hourglass is positioned atop the books, with the blurred background revealing a cozy seating area and dark blue walls.

4.98 out of 5 average rating, 280 reviews

Sycamore Cottage - Hot Tub - Steps to Downtown 2BR

Explore 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.

4.97 out of 5 average rating, 265 reviews

A white picket fence surrounds a lush garden, featuring a vibrant display of pink flowers. The fence complements the greenery of the landscape, with sunlight illuminating the blooms. The serene setting is ideal for enjoying the outdoors.

Cottage in Three Oaks

Lily’s Cottage, steps from Journeyman and Acorn!

Lily’s Cottage - Three Oaks, Michigan. Just steps to Journeyman Distillery and all other village sites including: Acorn Theater, Featherbone Factory Mercantile, Vickers Theater, Staymaker, Galleries, Shops, Antiques, Dewey Cannon Park, Bike Rentals, Nelson's Saloon, Drier's Meats, Froelich's and more! We are a no contact self check in rental. We are local and available by phone, text or airbnb email if needed during your stay.

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Popular amenities for Three Oaks places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Three Oaks

Twinkling string lights hang above a large deck area where wooden benches provide seating. A fire pit surrounded by Adirondack chairs is nestled in a landscaped yard. The backdrop showcases a charming farmhouse and grassy areas, inviting evening gatherings and relaxation.

5 out of 5 average rating, 29 reviews

Dreamy Wedding Stay, Perfect Family Getaway!

TranRating, 5 stars2 weeks ago

We had an incredible stay in Three Oaks, MI! Michelle was so friendly and responsive, and it was clear from the start how much she loves her town. She provided tons of thoughtful recommendations for local gems (Patellie’s! Granor Farms!) that made our trip even more special. The location was absolutely perfect for our reunion with friends—it offered plenty of space for everyone, including the little ones, to relax and enjoy. The s’mores kit and welcome gifts were such a sweet and thoughtful touch that made us feel right at home. We had an amazing time and would absolutely stay here again. Highly recommend!! :) :)

5 out of 5 average rating, 29 reviews

A kitchen countertop displays a green ceramic bowl filled with colorful dishcloths. Nearby, two vintage salt and pepper shakers are placed alongside a glass jar containing assorted items. A small photo in a frame adds a personal touch.

Apartment in Three Oaks

Three Oaks Guest Nest

ErikaRating, 5 stars1 week ago

My family & I had such a lovely stay at Bridget’s! It was very comfortable and Bridget & her family were super thoughtful with the small touches they provided- from the waters & snack to the sweet greeting cards. Thank you for making our stay a little extra special.

5 out of 5 average rating, 21 reviews

A charming brick building illuminated at night, featuring large windows displaying warm indoor lighting. The vibrant sign of 'Acorn Theatre' stands out, complemented by a parked vehicle in the foreground. Lush green trees frame the scene, enhancing the inviting atmosphere of the area.

Cottage in Three Oaks

Charming 3BD cottage-1 block to Journeyman & town

MaryBethRating, 5 stars7 months ago

Desiree is the perfect host. The Oaks is a beautiful home with everything that we needed. I highly recommend this home. We were in Three Oaks for a wedding at the Journeyman and The Oaks is a great location for that wedding. We were able to walk to the venue. Three Oaks is such a cute town.

A charming structure is surrounded by lush greenery, with large panes of glass allowing natural light to illuminate the interior. The exterior features a blend of white and dark accents. A spacious lawn offers a feeling of openness and serenity.

5 out of 5 average rating, 22 reviews

Woodside

AmberRating, 5 stars5 days ago

The girls and I planned a weekend getaway in this house. Our favorite part was the screened in porch in the middle of the yard. Us girls literally spent each night outside catching up. Such a wonderful weekend away at such a peaceful place. We would definitely come back.

An updated home is positioned at the center of the image, featuring a welcoming entrance with a decorative porch and large front steps. Surrounding gardens include well-maintained shrubs and trees. The sky showcases soft pink and purple hues as daylight transitions into evening.

5 out of 5 average rating, 97 reviews

Hot tub! In the heart of Three Oaks!

AngieRating, 5 stars1 week ago

Highly recommend! Extremely clean, fully equipped with all your essentials plus more!!! Host super helpful and quick to respond! Will stay here again!

A spacious outdoor deck features comfortable seating in woven chairs and a coffee table. A gas grill is positioned nearby, and a dining table with chairs is set under a shade umbrella. Lush trees surround the area, creating a serene atmosphere.

4.98 out of 5 average rating, 65 reviews

Elegant Guesthouse w/ Hot Tub, Walk to Downtown

JenniRating, 5 stars2 months ago

We 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!

5 out of 5 average rating, 52 reviews

Fascinating & Fun Family Haven w hot tub!

AshleyRating, 5 stars1 week ago

We really enjoyed our stay at Megan’s place. The house was perfect, especially for families with young ones. She made sure to have all accommodations in place that would be helpful for our family with two toddlers. The backyard was amazing and provided a variety of entertainment options. The binder left in the kitchen was a great resource and easy to follow. The location was within walking distance to the Three Oaks downtown area which was perfect for grabbing lunch, shopping or a coffee. Would highly recommend staying at Megan’s place!

Superhost

The kitchen features modern appliances, including a full-size refrigerator, oven, and microwave. Ample white cabinetry offers plenty of storage. Natural light enters through the window, illuminating the space with a view of outdoor greenery.