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

Great Living Too
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!

Rhain Rentals 3 Bed in St. Joe
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!

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

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

Irish Retreat
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.

New Buffalo / Farmesque with a splash of modern
We love this house! We try to stay once a year!

Long-Term Spacious House for Rent
Ruthanne was beyond helpful and attentive.

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

Charming Cottage on the Lake
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.

The Pines Cottage on Birchwood
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!

Harbor Country Michigan Hide-Away
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.

Van Auken Lake cottage rental
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!"

The Koi Cottage - Union Pier- Dog Friendly!
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.

The Lakeshore
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!

Designer Cottage Relax Beach Pool & Spa—Windjammer
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!

Sand Castles Cottages #7 Tiny House 1 Mile Lake MI
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

Stylish Lakehouse, Sandy Beach Includes lux Boat!
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!

Make Lasting Memories at Beautiful Lake Chapin
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!

Lakeside Getaway
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.

A Beautiful RETREAT home on a LAKE
Great staying here again. Even got an Irish win this time. Lake so serene with my morning coffee.

Secluded Log Home - Private Lake!
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!

Channel House on Indian Lake
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.

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

Pet friendly, lakefront, 3 kayaks & docks included
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.
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- Millennium Park
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- University of Notre Dame
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Museum of Science and Industry
- Willis Tower
- Lincoln Park
- Chicago History Museum
- Potato Creek State Park
- Washington Park Zoo
- Promontory Point
- Chicago Cultural Center
- Silver Beach Carousel
- Deep River Waterpark
- Point O' Woods Golf & Country Club
- Skydeck Chicago
- DuSable Museum of African American History
- Maggie Daley Park
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