Pet-friendly holiday rentals in Berrien County

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

Charming Downtown Sawyer Home Close to the Dunes

Enjoy this charming home in the heart of downtown Sawyer. Venture out on foot, and you're a 2 min walk to Greenbush, Infusco, Section House and more. Hop in the car and be at Warren Dunes or Journeyman Distillery in under 10 mins. Centrally located to be close to everything Harbor Country has to offer. Inside you'll find all the comforts of home, including a full kitchen, plush queen beds, as well as a 55" Smart TV with many apps ready to go on the Apple TV. Kitchen & bathroom basics provided.

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

Luxury meets nature: forest cabin steps from the beach, 1 hour from Chicago. Book your escape to our designer log cabin on Lake Michigan just steps from the beach and nestled in a peaceful forest, it’s the perfect retreat. Built in 1932, our charming cabin sleeps 8 in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit, games, puzzles & books. Featured in Country Living and the NYT, it’s perfect for families, friends, or retreats. Book now and create lasting memories in Michiana.

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. :)

Designer's Own Cozy Cottage

Kick back and unwind in this stylish getaway, ideally located in Union Pier and just a five-minute drive to New Buffalo. Tucked on the lake side of Red Arrow Highway, the Casita offers the perfect balance - close to all the action, yet a quiet retreat to call your own. Guests love visiting nearby beaches, indulging in baked goods, ice cream, local restaurants and wineries. Bike trails, hiking, pickle ball, golf and kayaking all nearby. Endless opportunities for relaxation and adventure await!

Secluded Garden New Buffalo/Lakeside MI

Enjoy every season at Dunedin Cottage, only 10 minutes from New Buffalo and in the heart of Harbor Country & the SW Michigan wineries. 3 lovely beaches in 2-3 minutes drive and parking. Great for families or groups celebrating weddings, birthdays or just relaxing. We have a fabulous garden (fully fenced) complete with fire pit, outdoor furniture, outdoor shower, large gas grill and lovely screened in patio. The fully stocked kitchen is a chefs delight complete w/ a large dining room table.

Hot tub & sauna, pet friendly, 1/2m to Hagar Beach

Peaceful, newly renovated 1930’s cabin walkable (1/2 mile) to Hagar Beach in the heart of SWMI. This pet-friendly home has a cozy feel with an outdoor hot tub, sauna, & fully-furnished spaces perfect for a relaxing getaway, remote work, or staycation home base while you explore the lake, bike trails, breweries, & eateries. Enjoy a quiet, off-the-beaten path stay close to everything Lake Michigan offers featuring a stocked kitchen, cozy reading nook & desk, and outdoor dining & fire pit.

Idyllic A-frame in Michigan’s Harbor Wine Country

Follow a wooded path to a secluded mid-century modern cottage constructed of stone and wood reclaimed wood from a historic St Joe's rollercoaster. Retro pink ceramic tiles line an open-plan main floor surrounded by sliding doors. You will be surrounded by the great outdoors while sitting cozy inside by our electric fireplace. Located about 10 minutes south of downtown St. Joe, our Idyllic A-frame is a perfect location for the escape to SW Michigan that you've been dreaming about.

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

Modern Minimalist Tiny House | Firepit | Nature

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.

Northwind Llama retreat “Chicken coop”

An escape to the country! Tucked away on a peaceful working llama retreat—voted the #3 stay in the state of Michigan—this charming efficiency suite offers a cozy retreat surrounded by nature. The thoughtfully designed space features ample seating for relaxing after a day outdoors with a convenient kitchenette. Step outside to not one, but two private gardens. A truly unique and tranquil getaway that blends comfort with award-winning countryside charm.

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

Discover the charm of New Buffalo from our cozy haven, perfectly located near the beach, Marina, and Bentwood Tavern. Explore downtown's treasures by foot, indulge in nearby wineries, or venture to Four Winds and Blue Chip Casinos. Nestled in Harbor Country's heart, our retreat is ideal for weekend escapes, families, or groups. Pets? They're welcome, with a secure fenced backyard for their delight. Experience New Buffalo's allure from our refined abode.