Vacation rentals in Lakeside

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Popular amenities for Lakeside vacation rentals

Stay near Lakeside's top sights

Blue Plate Cafe25 locals recommend
Flagship Fish Market5 locals recommend
Lakeside Antiques5 locals recommend

House rentals in Lakeside

Guest favorite
A spacious living area is presented with a comfortable gray sofa adorned with decorative pillows. Two accent chairs in a blue pattern complement a dark coffee table, while a computer desk is positioned nearby. Soft lighting is provided by recessed lights, and windows are dressed in sheer white curtains.
Home in Berrien Springs
4.95 out of 5 average rating, 124 reviews

Great Living Too

MichelleRating, 5 stars2 months ago
I cannot say enough about how clean the house was. Wonderful space for everyone. Kitchen table was large enough for my group to play games at and the basement space was large enough for everyone too! If we are back in the area we would stay here again!
Superhost
The exterior of a charming two-story home is showcased, featuring large windows that allow natural light to enter. A wrap-around deck with an umbrella offers outdoor seating, surrounded by well-maintained grass and shrubbery. The street is visible with a nearby view of the beach.
Home in Saint Joseph
5 out of 5 average rating, 3 reviews

Rhain Rentals 3 Bed in St. Joe

AshleyRating, 5 stars19 months ago
We very much enjoyed our stay at this rental! It the perfect size and location to all of the shops downtown and very accessible to the beach. The host was very responsive and so helpful with our stay. Highly recommend for a lovely weekend getaway!
Guest favorite
A private backyard features a stone fire pit surrounded by red cushioned seating. A dining table with chairs sits under a patio umbrella, and a gas grill is positioned nearby. Lush green grass and trees provide a natural backdrop.
Home in South Bend
4.89 out of 5 average rating, 114 reviews

Walk to ND/Eddy Street, ProCleaned/Comfy/Updated

AaronRating, 5 stars5 months ago
This is an awesome home - we came for a get together and a game with friends. The location is fantastic - incredibly walkable to the stadium, campus, and Eddy street. The house was perfect for our group - three TVs all going simultaneously was a great way to experience football weekend!
Guest favorite
The kitchen showcases a stainless steel stove and microwave, complemented by open shelving. A dining area with six metal chairs is positioned near the entrance to the living room, which features a sofa and a wall-mounted television.
Home in New Buffalo
4.81 out of 5 average rating, 398 reviews

Sq Toe's Last Resort:Pet-Friendly*Fenced* GameRoom

LaurenRating, 5 stars2 days ago
We had an amazing stay here- so amazing our dog didn’t want to leave on check out day! The location is GREAT. Everything is a 2 minute drive or 10 minute walk away and it’s quiet despite being in a neighborhood. We were very impressed with the restaurants in town too, we went to most of the places Ryan recommended. Brewers was our fav and Beer Church was a fun hang out spot! We also loved spending time playing ping pong in the garage shed. This place has everything you’d need, definitely want to come back in the summer.
Guest favorite
Two patterned armchairs with vibrant yellow and blue throw pillows are positioned near a window. A small round table with a decorative plant sits between the chairs. A plush area rug with a geometric design complements the seating arrangement, contributing to a cozy atmosphere.
Home in South Bend
4.86 out of 5 average rating, 166 reviews

Irish Retreat

MicheleRating, 5 stars4 months ago
We stayed at Linda’s while visiting family over the holidays and it was a comfortable, well stocked, clean, home away from home. It’s on a busy road but because of that close to everything. Linda was responsive and helpful. Kitchen had lots of condiments, coffee filters, cooking basics. Lots of extras like blankets, games, and box fans.
Top guest favorite
The exterior of the home features a vibrant orange facade with white trim and a covered front porch. Natural stone landscaping complements the entrance, and a garage is visible on the left. Surrounding trees suggest a serene outdoor setting.
Home in New Buffalo
4.92 out of 5 average rating, 315 reviews

New Buffalo / Farmesque with a splash of modern

KatieRating, 5 stars2 weeks ago
We love this house! We try to stay once a year!
Superhost
A functional kitchen is featured with wooden cabinetry and modern stainless-steel appliances. A stove, microwave, and sink are visible, alongside a window that allows natural light to enhance the warm tones of the cabinetry and floor.
Home in South Bend
5 out of 5 average rating, 4 reviews

Long-Term Spacious House for Rent

MaureenRating, 5 stars4 months ago
Ruthanne was beyond helpful and attentive.
Guest favorite
A spacious living area is highlighted by a large sectional sofa and a modern ceiling fan. Natural light enters through large windows, illuminating a decorative fireplace. A dartboard is mounted on the wall, and a small table is positioned nearby, enhancing the inviting space.
Home in South Bend
4.88 out of 5 average rating, 155 reviews

3BR w/sauna, tanning bed, hot tub 3.9 miles fromND

GlennRating, 5 stars1 week ago
For me it’s was an amazing experience. I absolutely loved the sauna. I am a cold natured person and the heat was relaxing. Do not get me started on the bidet! My first experience was well…let’s just say I’m probably going to put one in my home. Victoria was a super host! I travel the country building playgrounds and I’ve been staying at Airbnb homes for several years. Victoria made our stay here very memorable. 10+ on my scale of Hosting!

Cottage rentals in Lakeside

Superhost
A seating area is arranged on a wooden deck, featuring a sectional sofa and a coffee table. The sunset casts warm colors over the lake in the background, while silhouettes of trees frame the view. A boat is visible at the pier, enhancing the lakeside atmosphere.
Cottage in Decatur
4.89 out of 5 average rating, 122 reviews

Charming Cottage on the Lake

TyRating, 5 stars1 month ago
Our stay was very relaxing and tranquil. The scenery of the lake and the cleanliness of the house were amazing. Definitely would go back again.
Top guest favorite
A cozy cottage is nestled among lush green ferns and trees, with vibrant flowering shrubs nearby. The structure features a gabled roof and large windows, providing a glimpse of the welcoming interior. A picket fence frames the scene, adding charm to the natural surroundings.
Cottage in Michiana Shores
4.98 out of 5 average rating, 132 reviews

The Pines Cottage on Birchwood

JoshuaRating, 5 stars1 month ago
The Pines Cottage in Michiana Shores was the perfect escape for my sister and me—a busy Finance Director and Grants Manager—finally pressing pause on juggling responsibilities. Though it was a working vacation, this beautifully curated retreat by Meta Rose allowed us to relax, reconnect, and recharge. The blend of modern amenities with rustic charm made it feel like home, and the kitchen—my domain—was a dream for any home chef, snuggly designed yet perfect for cooking and baking. The serene surroundings and walkability gave us space for reflection and creativity, making our time here truly good for the soul. We can't rave enough about this little slice of joy and will absolutely be back! WARNING - you're going to fall in love all too easily with it!
Top guest favorite
An entrance area is visible, featuring a wooden cabinet displaying various dishes and decorative items. A sliding black door leads to additional spaces. Light-colored walls and hardwood flooring complement the warm wooden tones, while a bar stool is situated next to a kitchen counter.
Cottage in Union Pier
4.96 out of 5 average rating, 250 reviews

Harbor Country Michigan Hide-Away

JenRating, 5 stars1 week ago
We had a great time staying at Amy's place! It is the perfect size for a couple. It feels very cozy and like you are actually staying at someone's home vs. the sterile Airbnbs that are owned by corporate entities these days. The property is as described. It is very private, yet close to everything! I would recommend staying here if you're in the area.
Guest favorite
The exterior of the cottage showcases a spacious deck adorned with colorful Adirondack chairs. Large glass doors reflect the surrounding greenery, while landscaped flower beds provide a vibrant touch. A gas grill is visible near the deck, enhancing the outdoor gathering space.
Cottage in Bangor
4.95 out of 5 average rating, 198 reviews

Van Auken Lake cottage rental

CrystalRating, 5 stars6 months ago
The cottage was exactly what my husband and I needed for a little anniversay escape weekend. We intend to go back again with our teens who would love the lake-based amenities. As Goldilocks said, "It was just right!"
Superhost
A serene Koi pond surrounded by lush greenery is depicted, with vibrant fish swimming gracefully beneath the water's surface. Water lilies float on the pond, and a small waterfall gently cascades into the pool, creating a tranquil setting in the private yard.
Cottage in Union Pier
4.81 out of 5 average rating, 227 reviews

The Koi Cottage - Union Pier- Dog Friendly!

NicoleRating, 5 stars6 months ago
Cute, quaint and private cottage with a nice, large and completely fenced in backyard which is great if you bring the family dog. Good communication from host. No issues.
Guest favorite
A wooden dock extends over the calm lake, leading to a cottage surrounded by tall trees. Blue paddle boats are positioned on the shore, and the cottage features large windows that reflect the natural surroundings, with a peaceful yard visible in the background.
Cottage in Dowagiac
4.91 out of 5 average rating, 104 reviews

The Lakeshore

KristineRating, 5 stars7 months ago
Everything was perfect. Spent a relaxing weekend with my husband here. Went to the wounded minnow and the most amazing bacon ranch pizza. Spent the day on the paddleboats enjoying the sun. Ended our last night back at the minnow for a steak dinner and watched the sun set on the deck. Cute cottage, beautiful view. Sarah was so nice and always responsive. She even offered to allow us to check in early and check out later, great host with the most. Highly recommend checking her spot out!
Top guest favorite
Cottage in Union Pier
4.96 out of 5 average rating, 202 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

AparupaRating, 5 stars3 days ago
Rented the house for a girls weekend and it was perfect - comfortable to rest and relax in, spacious, quiet and private while still walkable to the beach and markets! Loved the decor and kitchen! We felt right at home!
Superhost
A sandy beach is seen leading to calm waters, with Hagar Park signage positioned at the top of wooden stairs. The shore is tranquil, marked by gentle waves and a stretch of the light grey shoreline, while overcast skies create a serene atmosphere.
Cottage in Lake Michigan Beach
4.79 out of 5 average rating, 163 reviews

Sand Castles Cottages #7 Tiny House 1 Mile Lake MI

MirandaRating, 5 stars6 months ago
John-Ross and Cara's AirBnB was so cute. They provided very clear instructions on how to get into the AirBnB and I had no issues the entire two nights that I stayed there. It was conveniently located to St. Joseph and South Haven. I would absolutely recommend this AirBnB to anyone who wants to stay in a unique cottage that is close to the lake!

Lakeside fishing vacation rentals

Guest favorite
A fire pit surrounded by two chairs is positioned on a grassy area near the lake. A wooden dock extends into the calm water, with colorful trees lining the shore visible in the background under a clear blue sky. The scene reflects a serene lakeside atmosphere.
Cottage in Dowagiac
4.9 out of 5 average rating, 49 reviews

Stylish Lakehouse, Sandy Beach Includes lux Boat!

StacyRating, 5 stars6 months ago
Kelly was easy to work with, had great communication, was very accommodating, and the cottages were so cozy & quaint! The biggest plus was getting the opportunity to use that amazing pontoon boat and getting out on the lake. We would definitely stay at this lake again! What a fun area. Having such a fun time we started looking at Kelly’s other properties for future getaways!
Superhost
A large, well-lit bedroom features double French doors leading to a deck overlooking the green landscape. Natural light streams in through the upper window, enhancing the spacious feel. Light-colored carpet is visible, along with a glimpse of a bed adorned with a floral pattern.
Guesthouse in Berrien Springs
4.92 out of 5 average rating, 246 reviews

Make Lasting Memories at Beautiful Lake Chapin

JordanRating, 5 stars1 month ago
Second time staying at this Airbnb in Berrien Springs, and it was a great escape from the city! Clean interior and king size bed were fantastic. It rained, so we didn't get to kayak, but it's great that we had the option. Would return again for a third time some day!
Superhost
A serene lakeside view captures a grassy shoreline leading to calm waters. A flagpole stands prominently, while boats are visible at a dock under a cloudy sky, suggesting a pleasant evening. Soft colors of sunset reflect on the water's surface.
Cottage in Decatur
4.94 out of 5 average rating, 93 reviews

Lakeside Getaway

SimonRating, 5 stars9 months ago
We loved staying at Michael's place. The setting is beautiful and private, and the cottage had exactly what we needed. Michael was a great host - responsive and willing to help.
Superhost
A spacious dining area is furnished with a long wooden table surrounded by several wooden chairs. Natural light floods in through large windows, providing views of the lake. Decorative elements such as hanging lights and ornaments add charm to the room.
Home in South Bend
4.79 out of 5 average rating, 42 reviews

A Beautiful RETREAT home on a LAKE

MarjorieRating, 5 stars7 months ago
Great staying here again. Even got an Irish win this time. Lake so serene with my morning coffee.
Top guest favorite
A secluded log home is depicted, surrounded by lush green woods. A spacious deck extends across the front, with seating and a hammock visible. A fire pit area features circular stones and bright red chairs, inviting relaxation outdoors.
Cabin in Hartford
4.97 out of 5 average rating, 316 reviews

Secluded Log Home - Private Lake!

MichaelRating, 5 stars2 months ago
We had an excellent time as a family at David's cabin. Everything was as advertised, and more. David was very proactive in communicating with us and responsive to any questions we had. The cabin was really, really beautiful, with peaceful surroundings and all the comforts of a well appointed home. David was clear about the pet policy and our dog was clearly welcome in the home. David left really nice touches for the humans as well, with cookies and muffins on our arrival. The house was well stocked with everything we needed, and we are particularly impressed with how well everything is labeled...light switches, cupboard doors, electronics, etc. Very, very well done. We enjoyed our long weekend, winter escape!
Top guest favorite
A spacious living area features a large sectional sofa in grey upholstery, accented by blue cushions. A round chair complements the seating arrangement. An area rug with a subtle pattern covers the floor, while a wall-mounted photo adds a decorative touch.
Cottage in Eau Claire
5 out of 5 average rating, 9 reviews

Channel House on Indian Lake

MariaRating, 5 stars8 months ago
Seven of us (3 adults and 4 teens- ages 12-18) enjoyed our stay over Labor Day weekend! Melissa stocked the house with games (indoor and outdoor!), linens, everything you’d need in a kitchen, and even firewood for the fire pit! We were delighted to find 4 kayaks with every size life vest we could possibly need in the garage. And the kids LOVED having a bunkhouse to themselves. We spent the weekend fishing, playing games, cooking, and enjoying a private channel off the lake. It was ideal! Melissa responded incredibly quickly and was kind and thoughtful from start to finish.
Top guest favorite
The lake house is positioned along the water's edge, featuring a spacious deck with outdoor seating and a fire pit. A private dock extends into the lake, with kayaks and floats available nearby. Lush greenery surrounds the property, enhancing the tranquil outdoor setting.
Cottage in Benton Harbor
4.97 out of 5 average rating, 77 reviews

Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.

AshleyRating, 5 stars1 week ago
Literally everything about this place was perfect. We thoroughly enjoyed our stay and wished we had more time to enjoy the property longer. The backyard is the lake, absolutely gorgeous views 😍 From the decor to the amenities, no detail was forgotten. Very impressed with the quality of materials, finishes, and furnishings in this home. The kitchen is a dream, bedrooms are beautifully done, delightful bedding, awesome game room/bar space, and outdoor setup has everything you could possibly need. The hot tub and fire pit were crowd favorites. Extra special thank you to our wonderful hosts for the top tier welcome basket and for being so helpful and responsive. Your place helped create a truly magical weekend.
Guest favorite
Chalet in La Porte
4.93 out of 5 average rating, 417 reviews

Pet friendly, lakefront, 3 kayaks & docks included

AshleyRating, 5 stars1 week ago
It was a cute and cozy lake house! We came to celebrate my fiancés 30th birthday and made it into a family weekend trip (two 6 year olds and a 6 month old) being our baby’s first trip. Sierra was a great host, checked in, and made sure we had everything we needed. The lake house is stocked with necessities and so cute! She has a guest book to fill out and add stickers and Polaroid pictures. Views are amazing. Our only wish was wishing it would have been warm enough to enjoy the lake. No complaints though! We’d love to come back in the summer to enjoy the outdoors on the water. 10/10

Your guide to Lakeside

Introduction

Chicago residents have been escaping to the southeast coast of Lake Michigan for a century, and hidden among the tree-lined beaches of Lakeside are thousands of rustic cottages and inns. This is a retreat designed for relaxation: You can hike in the woods, swim, bike, go wine tasting, or just do nothing — many people are here specifically to soak up the sun and spend long afternoons reading amid the trees. Many shops, bars, and antique stores along Red Arrow Highway cater to urban tastes, and the mood is serene and friendly. (Lakeside is not an isolated getaway, however, and if you need to buy supplies, Michigan City, just over the Indiana border, is only 20 minutes away.)


The best time to stay in a vacation rental in Lakeside

If you prefer gentle climates, May through September are definitely the best months to visit the southern Lake Michigan coast. The lake tempers the heat during the summer, but temperatures in the 80s Fahrenheit are still common. As July segues into August the humidity goes up — you’ll want to make frequent trips to the lake to cool down. (Essential protections: sunglasses, sunblock, and bug spray.)

Autumn, which begins in mid-September, is a magnificent time to stay in one of the area’s cottage rentals, with crisp air and brilliantly colored foliage. Winters stretch from early December to the beginning of March. During those months, temperatures below the 40s Fahrenheit are the norm, and the lakeshore effect brings freezing winds and snows to much of southern Michigan and northern Indiana.


Top things to do in Lakeside

Warren Dunes State Park

Warren Dunes is kind of the Riviera of the southern coast, with miles of fine-sand beach that fills up with castle-builders and sun-seeking teenagers. If you hear excited screaming, look up to see kids who have climbed to the top of a 250-foot sand dune flying or rolling down.

Red Arrow Highway

This north-south road connects the towns of the southeastern Michigan coast, and the stretch from New Buffalo to Bridgeman is lined with galleries, craft stores, and antique shops selling both knickknacks and high-end furniture. You can also find welcoming cafes, roadhouses, and a beloved Turkish restaurant.

Three Oaks

The town of Three Oaks, just a few miles inland from Lakeside, is the center of the region’s biking culture. You can rent bikes from little cruisers to heavy-duty mountain bikes, and there’s a bike museum. Three Oaks has created 20 bike routes that range from short and flat to September’s Apple Cider Century bike tour of wine and orchard country.

Destinations to explore

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