Vacation rentals in Lakeside

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Popular amenities for Lakeside vacation rentals

House rentals in Lakeside

Top guest favorite
An outdoor relaxation area features a hot tub and a smokeless firepit, surrounded by comfortable seating. String lights hang above, illuminating the space. A small set of steps leads into the hot tub, with a towel draped casually over the railing. The grassy area provides a serene backdrop.
Home in Three Oaks
4.99 out of 5 average rating, 103 reviews

Pet friendly stylish retreat with sauna, hot tub

JerryRating, 5 stars1 week ago
My wife and I have stayed at many vacation home rentals over the years, this one was one of the very best! First, I booked they house late afternoon on the day we wanted to arrive. Sarah responded immediately, accepted our booking and got me the access code to the property. It was all done within a few minutes! The house was beautifully decorated (my wife loved it and she is a designer!), well appointed and located very conveniently to all of the places we wanted to spend our time. We loved the hot tub, used the sauna almost every morning and our Golden Doodle loved the big fenced in back yard. Sarah and Brady are unbelievably responsive to needs too! One evening we wanted to enjoy the fire pit, but they were out of fire starters. I contacted Sarah at 7:36p, she responded at 7:37p and by 7:51 Brandy had already dropped a box of fire starters on the front porch! What?!?!?! Amazing. I HIGHLY recommend this place, we will be back!
Guest favorite
A fenced outdoor area features a gravel surface with a fire pit and two wooden benches. A green putting green is visible on one side. A covered deck provides shade and houses a grill. Nearby, trees and shrubs enhance the natural setting.
Home in New Buffalo
4.95 out of 5 average rating, 173 reviews

Steps to Beach & Starbucks! Private Yard, Firepit!

NicoleRating, 5 stars1 week ago
This is our second stay in this home. Quaint, clean, and in the heart of New Buffalo. We loved that our dog could join us! Plenty of towels, linens, cleaning supplies, and amenities that made our stay comfortable. I highly recommend!
Guest favorite
A newly renovated kitchen features modern cabinetry in muted tones, with light-colored countertops and a gas range. Stainless steel appliances include a refrigerator and a coffee maker. Natural light enters through a window above the kitchen sink, creating a bright and functional space.
Home in Three Oaks
4.96 out of 5 average rating, 136 reviews

The Heartwood House<3 : DT Three Oaks w/Game Room

LauraRating, 5 stars4 weeks ago
We had a great time in Three Oaks! This little house was everything we needed for a nice weekend away. It was an easy walk to downtown, had a lovely back yard, and all the bedrooms were quite comfortable. The kitchen was amazing and it all worked so well for our group. Thank you for having us, we will love these memories!
Superhost
The exterior of a log cabin is showcased, featuring a green metal roof and a spacious front porch with wooden seating. A gravel pathway leads up to the cabin, surrounded by lush greenery and trees. A small area for parking is visible in front.
Home in Sawyer
4.87 out of 5 average rating, 146 reviews

The Hideout near Warren dunes Red Arrow Cabins

ShanonRating, 5 stars4 weeks ago
We had a last minute stay for one night in this cozy little log cabin and had a great experience. The space was spotless and had everything we needed for a comfortable stay. Perfect for a quiet, short getaway. The host was responsive and check-in was smooth. Would definitely recommend for solo travelers or couples looking for a peaceful stay!! Our puppies loved it too!!
Guest favorite
An open great room features a large dining table at the center, surrounded by colorful chairs. A striking stone wall with a fireplace adds character, while large windows provide ample natural light. Cozy seating areas can be seen in the background, contributing to the inviting layout.
Home in Sawyer
4.94 out of 5 average rating, 159 reviews

Beautifully eclectic Sawyer cottage

OliviaRating, 5 stars1 month ago
This is the second year I rented this place for my birthday weekend away with friends. The house has so many accommodations for sleeping and different sitting areas. However, the main event is the kitchen. My friends and I love to cook and that's why we came back a second year in a row. The kitchen is unbelievably well-stocked with anything you might need to cook. There are multiple sinks so someone can be cooking while someone else cleans. The layout is perfect for people to hang out with whoever is cooking. There are two ovens. It is a dream. The house feels comfortable and lived-in, and it feels like there has been a lot of thought and intention focused on the user-experience. Cannot say enough nice stuff about this house, cannot recommend enough. Will be coming back for my 29 birthday.
Guest favorite
The vintage cottage is framed by lush greenery, featuring a welcoming front porch with a bright yellow door. A landscaped pathway leads to the entrance, with decorative stonework and potted plants accentuating the outdoor space.
Home in New Buffalo
4.84 out of 5 average rating, 219 reviews

Cozy Vintage Cottage Near the Lake

HollyRating, 5 stars1 week ago
Christiana’s place was exactly as described and perfect for a weekend getaway! It’s an adorable house, tranquil backyard, and walkable to everything- the beach, restaurants, bars, and the grocery store. You can literally park and not drive again until you leave. Christiana was very attentive and made sure we had everything we needed. We definitely would love to come back! If you’re a couple or foursome, this place is the perfect size with plenty of space.
Guest favorite
The living area showcases a modern design with a black sectional sofa and comfortable armchairs. A wooden coffee table is positioned at the center, and wooden beams complement the ceiling. A staircase leads to an upper level, while a large circular mirror enhances the space.
Home in Three Oaks
4.96 out of 5 average rating, 188 reviews

The Walnut House, Michigan Woods Retreat

ClintRating, 5 stars1 week ago
Cool place with great design.
Top guest favorite
A cozy firepit area is surrounded by five Adirondack chairs arranged on a gravel-strewn surface. Neatly stacked firewood is visible in the background, shaded by lush greenery and trees, creating a peaceful outdoor retreat.
Home in Harbert
4.97 out of 5 average rating, 196 reviews

Family Getaway with Year Round Hot Tub!

SandraRating, 5 stars2 weeks ago
Igor's Prairie Home was the perfect backdrop for my husband and adult children to take a break and reconnect as a family. The home is beautiful and so comfortable. We enjoyed the great hot tub and sitting around the fire pit. Oh and I don't want to forget to mention the tree house! How clever 🌞. Location is perfect for anything you'd like to do in the area because the house is located with easy access to Red Arrow highway. Either way you go there is plenty to see and do. Everyone wants to stay at Igor 's again and my son in law has already recommended to his parents. So I know we'll be back. 😎⛱️

Lakeside fishing vacation rentals

Guest favorite
Townhouse in New Buffalo
4.93 out of 5 average rating, 214 reviews

Location-Location Park and walk DT everywhere.

CaseyRating, 5 stars1 week ago
Joe is great and the place worked out great. Would definitely stay again. Perfect location.
Top guest favorite
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.
Cottage in Union Pier
4.97 out of 5 average rating, 138 reviews

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

TonyaRating, 5 stars2 weeks ago
We LOVED this place! Quiet, safe and friendly neighborhood which made it wonderful to relax and take several walks. Even a Nice short leisurely walk to the beach. We used the campfire pit a lot, since it was a cooler weekend than normal. The place was super clean, cute, cozy and comfy! Close to everything we wanted to do restaurants, ice cream, bike rides, etc. Peter was a wonderful host and even had a bottle of wine for us in the refrigerator to help celebrate our anniversary! We will be back!!
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
4.99 out of 5 average rating, 135 reviews

The Pines Cottage on Birchwood

KathRating, 5 stars3 weeks ago
We love this place. We’ve now been three times and are already planning our next time. The cottage has everything you need and is cozy and relaxing. Perfect for a lovely few days away from the hub bub of everyday. Meta Rose is proactive and responsive. We’ll be coming back again and again. 💕
Top guest favorite
The cottage exterior showcases a single-story structure with a light grey facade and a newly roofed design. Large windows allow natural light to enter, framed by a lush green landscape. A welcoming entryway leads to the home, complemented by garden pots and a gentle pathway.
Cottage in Miller
4.95 out of 5 average rating, 177 reviews

Neon Dunes Vista Beachfront Cottage

ReginaRating, 5 stars2 weeks ago
Great location and a very comfortable stay. The host was kind and easy to communicate with. Would definitely stay here again!
Guest favorite
A pontoon boat is docked in calm waters, surrounded by wooden docks. The clear water exhibits a gentle gradient, showcasing sandy bottom beneath. The horizon is visible under a clear blue sky, emphasizing a serene waterfront setting.
Chalet in La Porte
4.93 out of 5 average rating, 422 reviews

Pet friendly, lakefront home w/kayaks & pontoon!

HonorataRating, 5 stars2 weeks ago
We had the most amazing stay over Memorial Day weekend! The home was perfectly located right by the water, offering beautiful views and peaceful vibes throughout our trip. It was the ideal spot to relax and recharge. We brought our dog, Bruno, and he absolutely loved it too—lots of space to explore and enjoy the outdoors. The place was clean, comfortable, and had everything we needed for a stress-free getaway. We couldn’t have asked for a better experience. Highly recommend to anyone looking for a serene waterfront escape, especially if you’re bringing your pup along!
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, 416 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

SeleneRating, 5 stars2 weeks ago
I would recommend this place to anyone!!! Truly an above and beyond host and space was clean and inviting! Cannot wait to come back
Guest favorite
The dining area features a large wooden table surrounded by comfortable seating, illuminated by a modern pendant light. Nearby, the hot tub area is visible through large glass doors, nestled among lush greenery, providing a tranquil outdoor experience.
Home in Michigan City
4.98 out of 5 average rating, 111 reviews

Beach! Hot Tub! New Buffalo! Firepit! King Bed!

DavidRating, 5 stars2 weeks ago
Great private space on a quiet street. Lots of breweries and restaurants a quick drive away. Amenities were just as described and the space is in great condition.
Guest favorite
An outdoor fire pit area is surrounded by six teal chairs, arranged in a circular formation on a stone patio. The backdrop features a cozy brown cottage partially shaded by tall trees, with a gas grill visible nearby.
Cottage in Michiana Shores
4.97 out of 5 average rating, 172 reviews

Prime Summer Days Still Open @ Birchwood Cottage!

EricRating, 5 stars2 weeks ago
This is a wonderful find in Michiana Shores: close enough to the "action" of New Buffalo but secluded and peaceful. The walk/bike ride to the beach is very pleasant, but you may wish to stay in the backyard of the cottage to enjoy the beautiful surroundings/firepit. Grilling and eating outside on the large table was a blast. The outdoor shower is amazing, especially on a chilly morning! Don't miss a perfect Lake Michigan sunset at Stop 37-39 beach. Meals at Bentwood Tavern and Stop 50 Pizza (which you can WALK TO) were delicious as always. You will not be disappointed staying at this Cottage! A+ hosts and property!

Lakefront house rentals in Lakeside

Superhost
A round, dark outdoor table is surrounded by two cushioned swivel chairs with blue and white patterns. The scenic view of Lake Michigan, with gentle waves and a sandy beach, is visible in the background, framed by lush greenery on either side.
Home in Union Pier
4.87 out of 5 average rating, 30 reviews

Lakefront 4BR w/private beach & panoramic views

JillRating, 5 stars1 day ago
Our eldest was 85! Our youngest was 17 months old! Lots of ages in between! Everyone always found something to do! This is a spacious house and very practically furnished! You never feel crowded! I can’t think of a thing we needed in the kitchen! It was equipped with everything! The beach was pristine, with the waves of Lake Michigan, which you could see from the Sun/Game room! The walk down to the beach was so easy, and when you came back up to the house, you felt you had just had your workout for the day! Every time we had a question for the host or co-hosts, we had an immediate answer! If you want an easy, relaxing vacation, give ShangraLa a try!
Superhost
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
4.95 out of 5 average rating, 131 reviews

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

MichelleRating, 5 stars3 weeks ago
I rented Leah's home for my son's. They love to fish and Leah's home was the perfect place. They enjoyed the pontoon boat and sitting around the bonfire. The house was clean and kitchen equipped with everything needed for their weekend of grilling. Leah was a perfect host. Thank you, Michelle
Superhost
A private pool area is framed by a white fence, featuring a clear blue pool surrounded by lounge chairs. Lush greenery and a large tree provide shade, while the serene view of Lake Chapin and distant trees is visible in the background.
Home in Berrien Springs
4.9 out of 5 average rating, 125 reviews

Lake House Retreat with a Pool

KatelynRating, 5 stars2 weeks ago
This house was so beautiful and was a perfect place to spend a girl’s weekend! Would recommend over and over again and would definitely stay here again! Mike was also very quick at responding (even on the weekend) and when something wasn’t right he was very quick it fix it.
Superhost
A contemporary dining area features a large table surrounded by white chairs. A floral centerpiece adds color, while large windows offer views of the lake and outdoor deck. The kitchen area, visible in the background, includes wooden cabinetry and modern appliances.
Home in Cassopolis
4.93 out of 5 average rating, 60 reviews

Lake House in Cassopolis

MoniqueRating, 5 starstoday
Love this quaint house on the lake. We’ve stayed two summers now and call it the lake house. Love the views of the lake and the big back porch.
Superhost
A spacious two-story home is depicted, featuring a wooden deck with seating and a staircase leading to it. The exterior showcases a mix of siding and stone. The backyard, with trimmed grass, includes outdoor chairs positioned for relaxation.
Home in Cassopolis
4.95 out of 5 average rating, 110 reviews

Kelsey Lake Lake house 22 miles to Notre Dame

SheilaRating, 5 starstoday
We had a wonderful stay at this beautiful lake house for my nephews wedding at Marion Magnolia farms. Amy’s home is spotless and all finishes very high end. Every detail was well thought out. She even had a steamer - perfect for wedding attire! The bedding was also high end with cotton sheets on all beds (which is not typical of airbnbs. ). There was plenty of space for our family of 7 to be comfortable. The views were amazing and the boat and kayaks so much fun. Amy was great to work with throughout the process. We would definitely love to return to this special home.
Superhost
The exterior of a modern house is highlighted, featuring a striking architectural design with a triangular roof. Large floor-to-ceiling windows reflect natural light, while a sandy area is complemented by turquoise outdoor seating and a small dining set, creating an inviting outdoor space.
Home in Stevensville
5 out of 5 average rating, 28 reviews

Lakefront Home | Private Beach | Hot Tub

MichaelRating, 5 stars8 months ago
We recently spent a lovely weekend at Lake Solis. The house could not be more well stocked, cleaner or any more cozy and well designed. Every last detail is thoughfully designed to ensure a pleasant and comfortable stay. Out of all the houses in the development, this house has the best location, with a private beachfront and unobstructed views of the peaceful little lake. The host has been super friendly and accomodating. She requires no special rules upon checkout, instead wanting to make sure her guests simply enjoy their stay without having to worry about chores. And the best part - pets are welcome! Our yellow lab Bruno had an absolute blast, spending time in nature with all of us! Thank you!!!
Superhost
The eight-person hot tub features bubbling water with a view of Lake Michigan in the background. The surrounding area includes wooden loungers facing the water, providing a relaxing atmosphere to enjoy the tranquil scenery.
Home in Benton Harbor
5 out of 5 average rating, 27 reviews

Updated-Private Beach-Lake Views-Hot Tub-Fire Pit

LauraRating, 5 stars2 weeks ago
Beautiful views right on the coast of Lake Michigan. The place feels very cared for and has lots of great nooks to retreat to and just relax. We absolutely loved our stay and wouldn’t hesitate to return. Fair warning there are a lot of steps (my kids counted 169 to be exact) to get down to the beach but that didn’t deter us from going and the beach felt very private - we were literally the only ones there. It did limit our ability to send the kids without us for the younger ones which was fine but something to note if you were hoping to just watch them from the porch. We ate out pretty much the whole trip - highly recommend the Copper Pot and the cute market next door to it (pick out a charcuterie board from the cheese lady!). Overall a lovely trip! Thanks for having us!
Superhost
Two yellow adirondack chairs are positioned on a well-maintained green lawn, overlooking the expansive view of Lake Michigan. Bare trees line the area, and the clear blue sky reflects on the water's surface.
Home in Lakeside
4.93 out of 5 average rating, 30 reviews

Relax on your own private beach

RachelRating, 5 stars2 weeks ago
We stayed here for a friends trip of Memorial Day weekend and it was lovely! The walk to the beach was a short distance down the stairs, and the walk up the stairs definitely gives you a good workout. The hosts were very responsive to all messages that were sent during our stay. We hope to visit again!

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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