Pet-friendly holiday rentals in Three Oaks

Landmark Home 1 Blk from Lk MI w/Game Rm + EV Chgr

Sumptuous 4 BR/2.5 BA vacation home, just 1 block from Lake Michigan. Fully refurbished with reclaimed flooring, antique beams, custom doors, and fixtures. High-end kitchen, dining, and living areas with French windows. Living room features a stone fireplace, stylish couches, and a wide-screen TV. Three ground-floor bedrooms and baths with a second-floor bunk bed loft. Detached garage is a posh game room with high-end tables and a big TV. Covered patio, 4-seat dining, and bluestone courtyard. This property has been selected for inclusion in The 100 Collection, a global designation awarded to only the top professionally managed vacation rentals based on consistent quality and service. Classy, awe-inspiring, and sumptuous, this 1928 4 BR/2.5 BA vacation home, located just a block from Lake Michigan in “Harbor Country,” was once a local retail gathering place. Recently refurbished into a stunning residential home, it includes gorgeous reclaimed flooring from antique beams, custom doors, light fixtures, and hardware, as well as top-of-the-line plumbing fixtures. The kitchen-dining room-living room area—a massive, superbly well-lit space—features entire walls of French windows, original glass-block, and a wide array of seating options for meals: 4 chic stools at the white marble island, 4 leather seats around a circular marble coffee table, and a 10-seat reclaimed wood dining table. The beautifully lit living room has a classic stone fireplace at its center, stylish (yet ultra-comfortable) couches and chairs, and a wide-screen TV. In addition to the three bedrooms and bathrooms on the ground floor, there’s a second-floor sleeping loft, perfect for kids with cute bunk beds and a real (mini) teepee. All bedrooms feature top-quality bedding and linens, ensuring a sound sleep and sweet dreams for you and your guests. Black Door Bungalow can sleep up to 10. MAIN FLOOR Primary Bedroom: 1 King bed Bedroom 2: 1 Queen bed Bedroom 3: 1 Queen bed UPSTAIRS FLOOR Bedroom 4: Full-over-full bunk bed that sleeps 4 Another “extra” is the detached garage, which has been turned into a posh game room, with high-end shuffleboard and foosball tables, a big-screen TV, and a sound system. The exterior—featuring a spacious covered patio with cozy rattan couch, chairs, and a 4-seat dining table, leading to a bluestone courtyard—has been extensively landscaped with lush plantings, trees, and professional lighting. The home also includes a high-end kitchen, EV charger, and laundry appliances. In addition to being an easy walk from a majestic, crystal-sand Lake Michigan beach—and a super-short drive to popular beaches like Pier Street Beach and Cherry Beach—you and your guests can also enjoy the many activities afforded by being near Warren Woods State Park, which offers all sorts of woodland hiking and biking trails. The region’s largest recreational harbor provides countless water-related excursions and rentals, from fishing trips to boat, kayak, jet-ski, and paddleboard rentals, as well as day and evening cruises. There’s also the Acorn Theater, a local treasure for live performances by nationally recognized music artists, and a number of nearby breweries, wineries, brew pubs, and even an award-winning distillery for you to check out. Of course, you and your guests can also enjoy sampling to your heart's content the many popular restaurants, cafes, art galleries, boutiques, and antique shops just a hop, skip, and a jump away in Union Pier and downtown New Buffalo.

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!

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.

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. :)

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!

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!

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.

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus additional parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

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.

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

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

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!