
Vacation rentals in Lakeside
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Top-rated vacation rentals in Lakeside
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House rentals in Lakeside

Pet friendly stylish retreat with sauna, hot tub
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!

Steps to Beach & Starbucks! Private Yard, Firepit!
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!

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

The Hideout near Warren dunes Red Arrow Cabins
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!!

Beautifully eclectic Sawyer cottage
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.

Cozy Vintage Cottage Near the Lake
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.

The Walnut House, Michigan Woods Retreat
Cool place with great design.

Family Getaway with Year Round Hot Tub!
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

Location-Location Park and walk DT everywhere.
Joe is great and the place worked out great. Would definitely stay again. Perfect location.

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

The Pines Cottage on Birchwood
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. 💕

Neon Dunes Vista Beachfront Cottage
Great location and a very comfortable stay. The host was kind and easy to communicate with. Would definitely stay here again!

Pet friendly, lakefront home w/kayaks & pontoon!
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!

The Lake Escape -Cozy Lakefront Cottage Valparaiso
I would recommend this place to anyone!!! Truly an above and beyond host and space was clean and inviting! Cannot wait to come back

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

Prime Summer Days Still Open @ Birchwood Cottage!
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

Lakefront 4BR w/private beach & panoramic views
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!

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

Lake House Retreat with a Pool
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.

Lake House in Cassopolis
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.

Kelsey Lake Lake house 22 miles to Notre Dame
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.

Lakefront Home | Private Beach | Hot Tub
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!!!

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

Relax on your own private beach
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.
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- Millennium Park
- Navy Pier
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Willis Tower
- Potato Creek State Park
- Washington Park Zoo
- Chicago Cultural Center
- Promontory Point
- Chicago History Museum
- Adler Planetarium
- Silver Beach Carousel
- Deep River Waterpark
- DuSable Museum of African American History
- Museum of Contemporary Art Chicago
- Woodlands Course at Whittaker