Cottage vacation rentals in Lakeside

The Pines Cottage on Birchwood

The Pines Cottage on Birchwood is a cozy 2 bedroom 1 bathroom cottage with separate TV room perfect for a relaxing visit in Michiana Shores, IN. Walk to the private beaches at Stop 38 and Stop 41. Rear deck and front porch for quiet mornings with coffee or evening beverage. Situated .7 mile (10 min walk) from the lake & beach at Stop 38 and Stop 41, 6 minute drive to New Buffalo and Michigan City-it's perfect for a getaway to Harbor Country. Visit local breweries, wineries, and so much more.

Bright & Warm by Warren Dunes Maple St Beach House

Beautiful renovated house on wooded lot, half mile to the Warren Dunes! Home completely designed for the ultimate vacation rental getaway! SS kitchen, memory foam mattresses, marble bathrooms w/walk-in shower on main floor & full bath w/tub up, hardwood floors, gas fireplace in sitting area and great room that connects the living/dining and kitchen. Roast s’mores, grill steaks & sip local brews in the private backyard w/ fire pit. Central to everything in Harbor Country. Come enjoy winter w/us!

The Cottage of Harbor Country - Close to it all!

Welcome to your very own Cottage in Harbor Country! The perfect weekend getaway from Chicago, our cottage is close to Warren Dunes and just a 15-20 minute walk to Lake Michigan. Renovated and beautifully appointed, it blends vintage charm with modern updates! Enjoy morning coffee on the new deck or screened-in porch, take a dip in the new hot tub, or cozy up next to the wood-burning fireplace. Enjoy the perfect place to relax, hike, go antiquing, wine-tasting, and make memories with loved ones!

Beach Bliss | Pet Friendly W/Hot Tub Near Lake MI

Escape to our charming 2BR cottage just a few miles from the pristine shores of Lake Michigan. Our cozy retreat is the perfect place to unwind and enjoy all the beauty and activities of the Michigan coastline. With two comfortable bedrooms and an extra sleeping mat, our cottage can accommodate up to 5 guests, making it perfect for families and weekend getaways with friends! We also welcome your furry friends with a per-stay fee of $65 (max-2), so feel free to bring them along for the adventure!

The Birdhouse – quiet luxury, walk everywhere

The Birdhouse is on a quiet wooded ravine steps from restaurants, shopping and a lovely 0.7 mile walk to the beach. This home hosts 4 guests only, including infants. Enjoy a screened-in porch with views to the woods, an outdoor eating area with grill, lovely terrace with firepit and laundry room. Bedrooms are cozy and comfortable. The bathroom features a luxurious rain shower with hand shower for junior guests. To allow our cleaning crew time to prepare, we're unable to offer early check-ins.

It’s Sauna & Fireplace Season | Hot Tub| Sleeps 9

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

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.

Steps to the Beach! Screened in Porch & Firepit!

Experience the ultimate Harbor Country getaway! Just a 90-second stroll to a public beach access and under 5 minutes to another, this location is unbeatable. Spend your day soaking up the sun, kayaking, paddle-boarding, antiquing, golfing, or climbing majestic dunes. Discover endless local breweries, wineries, and top-rated restaurants. Unwind in the evening on the spacious screened-in porch or by the cozy firepit. Your perfect retreat awaits - adventure and relaxation all in one!

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

Hot tub! Red Tin Cottage of Harbor Country!

Welcome to The Red Tin Cottage of Harbor Country! Nestled in a quiet, rural setting Red Tin is a character-filled, country-chic escape in beautiful Southwest Michigan. Within minutes of award winning beaches, golf courses, wineries, breweries, and restaurants you can be close to it all and retreat back to peace. Take a dip in the hot tub on a starry night, relax in the claw foot tub after a day of play, or enjoy stories around the firepit with family and friends. Come gather!

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!