Cottage holiday rentals in St. Joseph

4.93 out of 5 average rating, 198 reviews

A cozy living room is featured with a soft beige sofa and an armchair in navy blue. A light rug with earthy tones is placed under a white coffee table, which holds magazines. A fireplace is surrounded by decorative mirrors, enhancing the welcoming environment.

Cottage in Stevensville

Cheerful Stevensville cottage, GREAT LOCATION!

Right in the prettiest area of Stevensville, Glenlord Cottage is an ideal location for your Southwest Michigan stay. Down the road you will find Glenlord Beach Park, a beautiful Lake Michigan overlook. Around the corner, an award-winning bakery. In Stevensville with its variety of restaurants, beaches, and shops, Glenlord Cottage is also within easy reach of many SW Michigan attractions and is well placed for visits to wineries, golf courses, and downtown St. Joseph with its shops and festivals.

4.99 out of 5 average rating, 104 reviews

A spacious living area features large French doors that open to a deck. A neutral-toned sofa is adorned with decorative pillows, while a wooden coffee table sits in front. An inviting armchair and framed artwork complement the warm, natural lighting filtering in.

Cottage in Sawyer

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!

4.8 out of 5 average rating, 191 reviews

An open kitchen and dining area is visible, featuring a dark wooden table with three matching stools. The kitchen is equipped with white appliances and blue cabinetry, illuminated by natural light from a nearby window. The flooring is a mix of dark wood and light tiles.

Cottage in Benton Harbor

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!

4.83 out of 5 average rating, 192 reviews

A private hot tub is visible, featuring a clear water surface and multiple jets. The tub is surrounded by a wooden deck, providing a relaxing outdoor space for guests to unwind.

Cottage in Three Oaks

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

4.91 out of 5 average rating, 148 reviews

A living area features a dark sofa adorned with yellow and blue accent pillows. Two light-colored armchairs flank a white coffee table centered on a striped area rug. Large windows provide natural light, with views of the backyard and sliding doors leading to a deck.

Cottage in Stevensville

Escape to The Sunshine Cottage of Harbor Country!

Cozy up at The Sunshine Cottage of Harbor Country. Surrounded by award-winning beaches, state parks, wineries, and breweries this location boasts endless activities within a short walk, bike, and drive. With a large backyard and extended porch deck, the cottage offers outdoor fun and entertaining all summer long, or retreat for a cozy winter getaway. The cottage is in close proximity to Lake Michigan and Grand Mere State park - sand dunes, hiking trails, and nature adventures all seasons.

A cabin-style home is nestled among tall pine trees, featuring a large facade with distinctive tall windows that allow natural light to flood the interior. Colorful chairs are positioned on the screened porch, surrounded by well-maintained greenery and flower beds.

4.98 out of 5 average rating, 243 reviews

"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.

Cottage in Michiana Shores

A charming cottage is nestled among tall pine trees, partially obscured by greenery. The natural surroundings create a tranquil setting, while the rustic stone chimney adds character to the cozy structure.

4.98 out of 5 average rating, 115 reviews

1930’s Cozy Cottage in the Woods.Walk to the beach

Come fall in love with Michiana Shores, we promise you'll love the peace and quiet. Our charming cottage sits back tucked away, nestled among pine trees and twinkle lights. Roast marshmallows while sitting around the fire with 6 modern adirondack chairs, take a stroll to the beach, ride bikes, BBQ, watch the sunset along lakeshore drive. Play tennis or pickle at the local park. 10 minute walk to the beach. Far away enough to relax yet close enough to new Buffalo, Union Pier or Long Beach

4.9 out of 5 average rating, 229 reviews

A well-maintained single-story home is seen alongside a spacious driveway leading to a two-car garage. The home features a charming front porch and neatly landscaped yard, with green grass surrounding the property and trees lining the background.

Cottage in Benton Harbor

Cottage near Hagar Beach Pet friendly with Hot tub

•Brand New Nordic Hot Tub• •September 2023 • Gather with family or meet with friends, there's plenty of room to stay the weekend. The inside of the home has refinished hardwood flooring throughout from the 1930's. The entire home is newly renovated giving it a classic Lake Michigan vibe. Only a few hundred feet from Lake Michigan's shoreline and one mile to pet friendly Hagar Park, there's a playground for the kids and plenty of beach to lay around on and enjoy with family and pet's.

4.97 out of 5 average rating, 166 reviews

A hot tub is visible in the foreground, with steam rising gently from the water. In the background, a rustic barn with a blue roof is framed by trees, and snow covers the surrounding area. Outdoor seating is arranged nearby, enhancing the tranquil winter setting.

Cottage in Sawyer

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!

The exterior of a modern home is displayed at dusk, featuring a well-maintained facade with soft lighting. An American flag is prominently displayed by the entrance. Surrounding grass is trimmed, and a peaceful wooded area is visible in the background.

4.8 out of 5 average rating, 160 reviews

Just 1 Mile to Lake Michigan

leisurely mile from 🐩 friendly Lake Michigan beach, HOT TUB 🥵 AVAILABLE! our stylish home offers a perfect blend of comfort and charm. 3 bedrooms, 1 bath, charcoal grill, picnic table and Wi-Fi. Unwind in the hot tub on crisp evenings under starlit skies. Explore local wineries, parks, lakes, and quaint shops, or dine at nearby restaurants. Relax on the stunning beaches and enjoy the tranquility of our quiet country setting. 15 minutes from St. Joseph and 18 from South Haven.

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

4.96 out of 5 average rating, 227 reviews

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!

An inviting cottage exterior features a wooden fence and a screened porch. Surrounding greenery showcases tall grasses and autumn foliage, creating an appealing atmosphere. A chimney and part of the roof can be seen, indicating the cozy interior space.

4.95 out of 5 average rating, 332 reviews

J’s Beach House: Hot Tub & short walk to beach!

J's Beach House is < a 5 minute walk to the beach! My cottage is equipped with a private hot tub and fireplace. Enjoy the walkable town or jump in your car for a quick drive to any Harbor Country activity! Potential for rental with adjacent cottage "Riley's Retreat". *Please inquire about our other Airbnb cottage near downtown Union Pier. This cottage is a 2-bedroom plus kids loft, screen porch, hot tub, fire pit, plus walking distance to Townline Beach!

Popular amenities for St. Joseph cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.88 out of 5 average rating, 132 reviews

The exterior of the cottage is shown, featuring a yellow siding with large windows that provide ample natural light. A small wooden deck is visible in front, furnished with a grill and seating. Well-maintained green shrubs and grass surround the property.

Cottage in Decatur

Charming Cottage on the Lake

A charming red cottage is nestled among vibrant autumn foliage. A screened-in porch with blooming flowers adds character, while a set of steps leads to a welcoming hot tub area. The exterior is complemented by neatly landscaped greenery and a gravel path.

4.85 out of 5 average rating, 470 reviews

The Oriole

A bright living area is showcased, featuring a sectional sofa in a calming blue hue. A large coffee table is centered on a patterned rug. A colorful dining set and a vintage-style orange fireplace are visible, while natural light illuminates the room through large windows.

4.92 out of 5 average rating, 371 reviews

Mid Century Meets Rustic Charm

4.97 out of 5 average rating, 132 reviews

An aerial view of the cottage is presented, surrounded by vibrant autumn foliage. A well-maintained path leads to the home, which is framed by trees showcasing hues of orange, red, and yellow. The outdoor seating area is visible, offering a cozy outdoor space.

Cottage in Fennville

Secluded dog-friendly cabin - hot tub & game room!

4.97 out of 5 average rating, 116 reviews

A modern white home is pictured, featuring a welcoming front porch supported by wooden posts. Multicolored stones create a path leading to the doorway, surrounded by neatly landscaped greenery on a newly mulched yard. Natural light reflects off large windows, inviting a peaceful ambiance.

Cottage in New Buffalo

Casa Playa - Union Pier Home w/ Pool & Private Spa

4.95 out of 5 average rating, 169 reviews

A charming yellow cottage is framed by a white picket fence and greenery. An American flag decorates the front, while a welcoming pathway leads to the entrance. Large windows with shutters provide light to the interior, complemented by a modest porch and seating.

Cottage in New Buffalo

The Lemonade Cottage, New Buffalo. Walk to beach!

A spacious deck with metal furniture is surrounded by tall trees and lush greenery. A nearby screen porch offers a view of the natural setting, creating an inviting atmosphere for relaxation outdoors.

4.97 out of 5 average rating, 269 reviews

Harbor Country Michigan Hide-Away

4.93 out of 5 average rating, 437 reviews

The tranquil surface of Flint Lake reflects a colorful sunset, with soft hues of pink and orange blending into the serene blue sky. The surrounding tree line is silhouetted against the fading light, creating a peaceful and calming atmosphere.

Cottage in Valparaiso

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Pet-friendly cottage rentals

4.96 out of 5 average rating, 82 reviews

The exterior of the cottage is presented, showcasing a spacious screened-in porch framed by greenery. The flat roofline and large windows invite natural light, while a neatly landscaped area with a stone border enhances the tranquil setting. Lush grass complements the peaceful environment.

Cottage in Sawyer

Rosie’s Cottage close to Warren Dunes (w pool)

4.97 out of 5 average rating, 228 reviews

A contemporary living area features a brick accent wall with a fireplace, providing a cozy focal point. Blue accent chairs are positioned nearby, while a spacious gray sofa invites relaxation. A wooden coffee table sits centrally, and large windows offer views of the surrounding nature.

Cottage in Douglas

Mid-Century Modern Luxury Near Douglas Beach

5 out of 5 average rating, 28 reviews

A view from the deck captures the expansive lake with a wooden dock extending into the water. Multiple boats are visible, anchored in the calm lake. The sky is partly cloudy, allowing natural light to illuminate the scene, while green grass borders the deck area.

Cottage in Watervliet

Modern Lakehouse | Dock | Firepit | Kayaks | BBQ

A wooden deck features a seating area with four wicker chairs and a central glass-top table. Bright blue cushions add a pop of color, while a nearby bench complements the setting. The surrounding greenery provides a serene backdrop, enhancing the outdoor space.

4.77 out of 5 average rating, 105 reviews

3 min to Beach on Lake Michigan Wine Trail

A view from the cottage patio shows Adirondack chairs set on a wooden deck, surrounded by greenery and colorful flowers. In the background, Lake Kalamazoo is visible, along with a gazebo and a grassy area leading towards the water.

4.98 out of 5 average rating, 260 reviews

Dumela-Cozy Cottage w/ Views In Historic District

The image displays a light blue cottage framed by lush green trees, featuring a front porch with outdoor seating. A flag is displayed prominently. Additional views include a serene lake and an interior with bunk beds, showcasing a cozy and functional sleeping area.

4.83 out of 5 average rating, 35 reviews

Paw Paw Lake|Cottage|Lake Access|Herons Nest #6

The exterior of the cottage is shown, featuring a mix of siding in varying shades of gray. Two potted plants in black containers frame the entrance, while a porch with a railing adds a welcoming touch. Lush greenery surrounds the property, enhancing the inviting appearance.

4.81 out of 5 average rating, 242 reviews

The Koi Cottage - Union Pier- Dog Friendly!

A circular stone patio surrounds a fire pit, with several black wooden Adirondack chairs arranged for seating. A spacious deck extends behind the fire pit, leading to a cottage surrounded by trees, creating a natural and tranquil outdoor setting.

4.81 out of 5 average rating, 232 reviews

Dog Days of Summer Cottage

Private cottage rentals

The exterior of the cottage is surrounded by trees, with a designated seating area featuring two blue Adirondack chairs and a wooden table. A firepit sits in the gravel yard, offering a natural gathering space among green foliage.

4.97 out of 5 average rating, 150 reviews

Beach Bird Cottage- 5min walk to the lake! 3BR/1BA

5 out of 5 average rating, 47 reviews

A decorative pillow with the word 'RELAX' prominently displayed is centered against dark blue pillows. The soft bed linens provide a serene backdrop, contributing to a calming atmosphere suited for restful retreats.

Cottage in South Haven

South Haven/Saugatuck-Walkto Private Lake MI Beach

4.94 out of 5 average rating, 256 reviews

A scenic view of sand dunes leading to Lake Michigan is displayed, with tall grass swaying gently in the foreground. Text highlights features of The Blue Shore Cottage, emphasizing total sleep capacity, baby amenities, beach access, and kitchen provisions.

Cottage in South Haven

Lake Access|Spacious Cottage&Guest House|Sleeps 12

4.87 out of 5 average rating, 54 reviews

A charming blue exterior of a home is framed by lush greenery and a well-maintained pathway. The inviting front porch features bright red chairs under a pergola, with large glass doors providing a glimpse into the interior.

Cottage in Lakeside

Private Hot Tub and Association Beach!

4.95 out of 5 average rating, 42 reviews

A cozy living area features two gray sofas adorned with decorative cushions. A coffee table sits in the center, complemented by a shelf displaying various decorative items. Natural light enters through two windows, flanked by soft gray curtains.

Cottage in Benton Harbor

Nauti Cottage-Minutes from St Joe-Dog Friendly

An outdoor gathering area is surrounded by tall trees, with a firepit at the center. Bright string lights hang above, creating a cozy ambiance. Colorful Adirondack chairs are positioned around the fire, and a stack of firewood is neatly arranged nearby.

5 out of 5 average rating, 21 reviews

Wooded retreat with HOT TUB & Game Room

4.93 out of 5 average rating, 59 reviews

A sunlit sunroom features a blend of natural wood and wicker furnishings. Two wicker chairs with green cushions and a small table are arranged comfortably, alongside a round rug. Large windows allow natural light to fill the space, enhancing the cozy atmosphere.

Cottage in Bridgman

Cheerful 2 bedroom cottage with vintage vibes!