Pet-friendly holiday rentals in Michigan City

-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.

Blue Chill | WalktoBeach | HotTub-all yr | Dogs OK

Launch your fabulous beach getaway from daily stresses and bring your group – and pet – on a road trip to fun and games just a mile from Washington Park Bch. The 8-person hot tub will feel delightful after a day on the beach or nearby shopping, and attractions. Grill and dine in the private backyard; then gather 'round the firepit under mood lighting. Garage game room has it all, with cornhole, Foosball, a 55" ROKU TV, and seating, with board/card games available. Enjoy 1-level living, 2 baths.

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.

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.

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub

Luxury farm retreat on 7 wooded acres with hot tub, yoga shed, fire pit, fully fenced yard & pond! This home is a five minute drive to the beach, blueberry picking, Burn 'Em Brewing, Shady Creek Winery, next to Tryon Farm or 10 minute drive to downtown, the casino, and the outlet mall, but our guess is that you won't want to leave the property! This designer home has super comfy beds, 800 thread count sheets, a gourmet coffee bar, screened in porch, and even a tiny library in the laundry room

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!

Perfect 1 Bed Penthouse Steps To Beach w/Parking!

Looking to spend some time away from the chaos of life and stay in a beautifully updated home steps from the beach on Lake Michigan? Welcome to Sheridan Beach in Michigan City! This perfect 1 bed/1 bath penthouse unit is situated within a block of the beach/water. The serenity of the neighborhood and seclusion from the outside world are its most attractive features. Located a little over an hour from Chicago, it's a quick drive to enjoy some R&R. Get ready to make some amazing memories.

TRYON FARM MID-MODERN SPA IN THE WOODS

Come, enjoy our Tryon Farm modern spa. A Sustainable luxurious open concept tree-house in the woods. Minutes from the beach with an outdoor sauna, Hottub, shower, and Mr. Steam. Perfect for two or a family/group adventure. A true destination with Yoga studio, Mirror by LuLu lemon and wellness elements. The house is a perfect balance of art and nature and luxury and spiritual. Treat yourself to a farm to table, hand made, locally sourced chef services for an extra special experience.

Wanderlust Loft at Lake Michigan

WANDERLUST LOFT is located in the Michigan City Arts District, within walking distance to beautiful Lake Michigan and Washington Park. On the way is the Washington Park Marina, the Lubeznik Center for the Arts. You’ll love the location, the colorful interiors, and the open living space of the WANDERLUST LOFT. It's a great place to explore your inner wanderer and to discover the good life. Perfect for couples, solo adventurers, business travelers, and furry friends (pets).

cozy new buffalo cabin, hot tub, 14m walk to beach

Kick back and relax in this calm, and cozy stylish space , Brand new home . Full of windows to gaze into the forest , very private. This is the guest home behind main home . Heated polished concrete floors and a screen porch highlight the experience along with the hot tub and ultra private setting of home . 3 large bedrooms, large great room and kitchen , dinning upscale gathering area . Small train tracks next door , it runs 3-5 times a day ( usually short train ).

Midcentury marvel steps from beach! Pups

Year-round beach fun an hour from Chicago!Welcome to Barefoot Bungalow, a mid-century marvel with modern amenities. Your group will love the game room with pool table, ping pong. Private dog-friendly fenced backyard with grill, patio & firepit. Short stroll to Stop 7 to beach (Beachwalk boardwalk, wagon provided). Quiet relaxation far from the madding crowds. So many excellent restaurants, shopping, brew pubs, wineries, hiking, biking. Off-street parking, Wave bus

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!