
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
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.

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 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.

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

3BR w/sauna, tanning bed, hot tub 3.9 miles fromND
loved staying here. Victoria was friendly and responsive. wish we had more time in the unit to enjoy the extras.
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.

Harbor Country Michigan Hide-Away
We really enjoyed our stay. Amy communicated well, house was clean and had everything we needed.

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!"

Cozy, Quiet Cottage with so much Character! Clean!
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.

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
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

The Lake Escape -Cozy Lakefront Cottage Valparaiso
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

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

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

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.

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.

Private Vandalia Beach Front Cottage
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!

Pet friendly, cozy, lakefront home on Pine Lake
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.
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- Millennium Park
- Navy Pier
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- University of Notre Dame
- Museum of Science and Industry
- Lincoln Park Zoo
- Chicago History Museum
- The Field Museum
- 875 North Michigan Avenue
- Potato Creek State Park
- Willis Tower
- Lincoln Park
- Chicago Cultural Center
- Promontory Point
- Silver Beach Carousel
- Washington Park Zoo
- Point O' Woods Golf & Country Club
- Skydeck Chicago
- Deep River Waterpark
- South Bend Country Club
- Adler Planetarium
- Museum of Contemporary Art Chicago
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