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 Market24 locals recommend
Lakeside Antiques16 locals recommend
Hearthwoods Custom Furnishings5 locals recommend
AP Shop5 locals recommend
Frecklefarm3 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, 123 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, 394 reviews

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

MeganRating, 5 stars2 weeks ago
Very nice house, very clean, and amenities and snacks were provided. Quick walk or very quick drive to downtown New Buffalo. We loved the game room!! One note for dog owners: there’s no direct access from the house to the yard, you have to bring the dog onto the front stoop to access the gate to the backyard. So just something to be aware of if you have a dog that likes to bolt.
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 stars3 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.
Guest favorite
Home in New Buffalo
4.92 out of 5 average rating, 314 reviews

New Buffalo / Farmesque with a splash of modern

BrianRating, 5 stars3 weeks ago
We absolutely loved staying at Tim's place in New Buffalo. The house is super cute, can sleep everyone comfortably, and is in such a great location. We look forward to making this an annual trip.
Superhost
A historic house features a stone and siding exterior with a covered front porch. The entrance is framed by columns, and a pathway leads to the front door. Windows with a decorative upper design provide natural light to the interior.
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, 153 reviews

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

WilliamRating, 5 stars2 weeks ago
loved staying here. Victoria was friendly and responsive. wish we had more time in the unit to enjoy the extras.

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
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, 248 reviews

Harbor Country Michigan Hide-Away

LawrenceRating, 5 stars1 month ago
We really enjoyed our stay. Amy communicated well, house was clean and had everything we needed.
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 stars5 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!"
Guest favorite
The cottage exterior, framed by trees, features a charming pergola with string lights. Several Adirondack chairs are positioned near the lush green lawn, inviting relaxation. A cozy hammock hangs nearby, enhancing the outdoor experience, along with a visible firepit area perfect for gathering.
Cottage in Goshen
4.95 out of 5 average rating, 512 reviews

Cozy, Quiet Cottage with so much Character! Clean!

HollieRating, 5 stars4 days ago
I loved every second of my stay at this sacred little space. The bonfire pit, the hammock, the pergola were all so welcoming on this beautiful spring weekend. I spent time every day in the hot tub, which was amazingly clean and peaceful. Although the outdoors is shared, it's plenty spacious and I felt like I had 100% privacy all weekend long. The house itself is PERFECT. It's small but spacious. The bathroom is top notch. The tiny kitchenette was all I needed. I brought my mini airfryer and was completely happy. All of the special touches made the decor so interesting and unique. Got to spend some time in Goshen and in Elkhart to shop and eat. I left feeling absolutely recharged. This is going to be on my tiny house rotation for sure. Highly recommend. If I could give ten stars, I would.
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, 200 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

SarahRating, 5 stars2 weeks ago
Birthday brownies upon arrival! Great quiet location but very convenient for local shops and restaurants. Can walk to the beach! Can’t wait for the opportunity to visit again
Guest favorite
Large windows provide a scenic view of Flint Lake and a deck area featuring an umbrella and lounge chairs. Soft sunlight filters through the trees, illuminating a cozy seating area adorned with floral cushions.
Cottage in Valparaiso
4.93 out of 5 average rating, 411 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

KimberlyRating, 5 stars3 days ago
My daughters and I celebrated Easter at Kim’s cottage It’s clean, beautifully furnished and she is extremely responsive (I mentioned I forgot OJ on the phone and she was in the area and she left two OJs at the door) The cottage is cozy and fun We grilled, dyed eggs, watched movies, played a board game and loved the hot tub It’s clean clean !!! Just book it It’s a jewel box
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 lakefront view reveals a charming house with a porch and multiple seating areas on the lawn. A private dock extends into the water, accommodating a pontoon. Green trees provide shade, while an American flag gently waves in the breeze.
Home in Valparaiso
4.94 out of 5 average rating, 127 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

JamesRating, 5 stars6 days ago
Leah was a phenomenal host, very responsive and fast with her replies to my questions. The place was super comfortable and welcoming. It was peaceful and quiet just as advertised. Had a wonderful stay!
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!
Guest favorite
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 stars3 weeks 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
The exterior of a charming cottage is visible, featuring a sloped roof and a large porch with clear glass windows. Colorful chairs are arranged outside on the porch, overlooking a well-kept grassy yard. Surrounding homes are partially visible in the background.
Cottage in Decatur
4.94 out of 5 average rating, 93 reviews

Lakeside Getaway

SimonRating, 5 stars8 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.
Top guest favorite
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 sunlit sunroom features large windows that allow natural light to fill the space. Comfortable seating is arranged, including a spacious couch and armchairs. A small table occupies the center, while a television is mounted on the wall. A welcome mat greets visitors at the entrance.
Cottage in Eau Claire
5 out of 5 average rating, 9 reviews

Channel House on Indian Lake

MariaRating, 5 stars7 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.
Guest favorite
A cozy living area features a leather sofa and a patterned chair, offering comfortable seating. Large windows allow natural light to fill the space, showcasing views of Paradise Lake. A small side table holds a laptop and decorative items, enhancing the inviting atmosphere.
Cottage in Vandalia
4.9 out of 5 average rating, 21 reviews

Private Vandalia Beach Front Cottage

AmyRating, 5 stars7 months ago
This was such a nice weekend with our family. The cottage was stocked with everything you need! The lake is super quiet and pretty private! The place was clean and remodeled in the inside. Our first time booking an AIRBNB so we were nervous but we are so glad we did!
Guest favorite
Chalet in La Porte
4.93 out of 5 average rating, 413 reviews

Pet friendly, cozy, lakefront home on Pine Lake

JustynaRating, 5 stars4 days ago
We absolutely loved staying at your place! Fishing right off of the deck/dock was just amazing! My boyfriend did not want to leave!! Sierra was gracious and allowed us to check out few hours later. Place is super cute and has everything you need. Can't wait to return AND we definately planning on returning - we loved it soo much! One of the best spots for relaxing weekend getaway! Thank you!

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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