Holiday houses 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

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

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.

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

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.

Guesthouse in New Buffalo

4.98 out of 5 average rating, 838 reviews

"Tiny House" Guest House - No Cleaning Fee

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

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!

4.98 out of 5 average rating, 109 reviews

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!

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!

4.99 out of 5 average rating, 127 reviews

Poplar Place - Hot Tub - 3BR - Steps from Downtown

Explore the wonders of Michigan's Harbor Country while staying in our relaxing private home, Poplar Place. 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

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 holiday rentals

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Pool

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Other great holiday rentals in Three Oaks

Superhost

Cabin in Three Oaks

4.84 out of 5 average rating, 92 reviews

Cabin with POOL & sandy BEACH in family resort!

JamesRating, 5 stars6 days ago

Wonderful place! Outstanding deck which almost doubled as a second home outside! Endless amenities inside and around the resort to entertain a couple or large family for a weekend getaway! Nicely decorated and plenty of beds—especially in the loft for the younger kids! Near the red arrow highway so easy to navigate around nearby towns as well. Awesome hosts that were very responsive and kind. Highly recommend!

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

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

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.

4.98 out of 5 average rating, 65 reviews

Elegant Guesthouse w/ Hot Tub, Walk to Downtown

JenniRating, 5 stars3 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!

Superhost

4.92 out of 5 average rating, 25 reviews

Downtown charm: walk to shops & 10 min to beach

LoriRating, 5 stars6 months ago

Vincent's place was exactly as described and had everything we needed. The home was clean, comfortable, and well-equipped with extras like games. The beds were great, with plenty of spare blankets and towels. Vincent was an excellent host, providing clear communication about the Wi-Fi, keypad, and local tips. Three Oaks is a charming town with a lovely downtown full of shops and restaurants. We enjoyed meals at Patellie’s (pizza and sandwiches), Featherbone (dinner variety), and Oaks Eatery (brunch). Though the freezing weather (20s and snowing) had us driving, everything is within walking distance in better weather. The beautifully restored home was cozy, and while the fire pit looked inviting, it was too cold to use. As a fun bonus, we discovered Three Oaks is the filming location for "Prancer". Watching the movie and spotting familiar places added to the experience. Meeting our kids here for Thanksgiving was wonderful, and we’d love to return!

4.96 out of 5 average rating, 85 reviews

Happy Acres: Modern Luxury Country Farmhouse

LeahRating, 5 stars3 weeks ago

Beautiful place to relax! We unfortunately were super busy during our stay and couldn’t enjoy anything the owners recommended in their binder, but we would love to come back and take advantage of what is around us. House was perfect, clean, stocked with everything. Bathroom/shower is a wet room, could be slippery for elderly population, but owners explained how to use that in binder. We will use this home for future visits to ND!