Pet-friendly vacation rentals in Three Oaks

A bright and airy living space reveals a cozy area featuring a light-colored ottoman and a sleek fireplace. A large indoor plant adds a touch of greenery, while a doorway leads to a well-lit bedroom area beyond. Modern furnishings are visible within the serene environment.

4.87 out of 5 average rating, 120 reviews

Walk downtown in Three Oaks Modern Victorian Home

Beautiful, large & comfortable vintage Victorian home with modern touches. Home features grand rooms, comfortable premium furnishings & vintage details throughout. Outside, you'll find a spacious fully fenced-in backyard, with plenty of room to play or relax in the sunshine, or by the firepit! Just steps (0.2 mi) to Journeyman Distillery and all that downtown Three Oaks has to offer. Central to all in Harbor Country like beaches, wineries, breweries and farm stands. Come relax in style with us!

4.98 out of 5 average rating, 299 reviews

A covered porch area features a wooden sofa adorned with decorative pillows, offering a comfortable seating space. A dark outdoor table stands beside it, creating a cozy spot for relaxation. Natural light pours in through the surrounding large windows, enhancing the tranquil ambiance.

Home in Michigan City

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

A comfortable living space features a vintage green cabinet and a wooden dining table surrounded by black chairs. Natural light floods the room through large windows, enhancing the cozy atmosphere created by soft furnishings and decorative plants.

4.97 out of 5 average rating, 211 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, 175 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

Cottage in Three Oaks

4.83 out of 5 average rating, 182 reviews

Pickleball & Volleyball Nets |Hot Tub| Sauna|Beach

Wanna Play?? You name the game & we most likely have it! Outdoor fun includes YEAR-ROUND hot tub, Pickleball & Volleyball nets, Soccer goals, Putting Green, corn hole and even cruiser bikes. Indoor fun incl. complete poker table/set & a ton of board games! If you prefer to take it easy you can relax by our indoor fireplace or the outdoor fire pit, recharge in the YEAR-ROUND indoor sauna or stroll to nearby Harbert Beach. Whatever your choice, THIS is the place to experience Harbor Country

The living room features a modern design with a mounted television above a sleek fireplace. Two comfortable armchairs flank a wooden coffee table, while natural light filters through the large windows, complemented by light-colored shades. A neutral rug adds warmth to the space.

4.98 out of 5 average rating, 162 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!

4.91 out of 5 average rating, 160 reviews

The exterior of the cottage is showcased, featuring a welcoming dark grey facade. The front yard contains well-maintained greenery and small trees. Two large picture windows allow natural light into the interior, while a small patio leads to the entrance.

Cottage in Union Pier

Camp Wanderlust-Cozy lodge-20 minute walk to beach

A place to wander with the ones whose company you enjoy. Enjoy a cozy getaway, in our quiet cottage. 10 minute walk from shops and brewery and restaurants of Union Pier. 10 minute walk to Winery Tasting. 20 minute walk to Townline Beach. Union Pier is the perfect beach town in the heart of harbor country, enjoy exploring this magical region or maybe just kick back and build a fire and enjoy the space. 1914 a colony of Chicago bohemians, vacationed at the "Camp's Cottages" at Union Pier.

Superhost

The exterior of a modern tiny house is seen surrounded by trees. Soft lighting strings hang above a fire pit with four Adirondack chairs arranged around it. Smoke rises from a fire, creating a cozy outdoor space.

Tiny home in Sawyer

4.91 out of 5 average rating, 129 reviews

Modern Minimalist Tiny House

Welcome to our modern minimalist tiny house located a half mile from Warren Dunes State Park beach and 1.5 miles from all that Sawyer Michigan area has to offer. Tiny is the second dwelling on this property and is technically a mobile tiny house. While we do have electricity and water, much like an RV the drains run to holding tanks. This means VERY LIMITED WATER USE for showers and toilet flushing. It features a fully stocked kitchen, bathroom, and a queen bed in the small loft.

The image displays a stylish living room featuring light-colored walls and a geometric area rug. A modern light fixture hangs above a rectangular coffee table, complemented by two leather chairs. The exterior view showcases a two-story home with a welcoming front porch and a blended color scheme.

4.99 out of 5 average rating, 117 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

A charming yellow cottage is surrounded by greenery and vibrant flowers. The home features blue shutters and a welcoming front porch with white railings. A paved pathway leads to the entrance, framed by well-maintained grass and landscaping.

4.99 out of 5 average rating, 150 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, 167 reviews

The image captures a charming dark blue barn house framed by trees adorned with vibrant autumn leaves. A carpet of fallen leaves covers the ground, creating a colorful, natural setting. A patch of green grass contrasts gently with the autumn hues surrounding the structure.

Barn in Stevensville

The Blue Barn - A cozy country getaway!

Welcome to “Blue Barn” vacation home, a country retreat located between beautiful St. Joseph beaches and several Baroda wineries. A welcoming, open floor plan makes it easy for your group to spend time together. Enjoy the crisp white bedding, fully stocked coffee and wine bar, and private fire pit to unwind with friends and family. Grand Mere State Park, Weko Beach, and several local breweries are all just a short drive from this ideally located property.