
Cottage holiday rentals in Lakeside
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Top-rated cottage rentals in Lakeside
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Popular amenities for cottage rentals in Lakeside
Cottage rentals with a hot tub

The Cottage of Harbor Country - Close to it all!
My two kids and I loved staying here. It’s a special and cozy place to get away for a few days. We especially loved the hot tub! Herb was extremely responsive and an A+ host!

The Great Escape: Blocks From Your Private Beach
My friends and I stayed for the weekend for a birthday getaway and loved it! Trevor's place was just as described and felt so cozy. The location was perfect! We enjoyed early morning walks around the neighborhood and by the lake, as well as sitting out on the porch and by the fire pit. We were so close to town where there are so many lovely restaurants and shops. Trevor provided recommendations for a few places that we did end up checking out and they were amazing! The Terrace Room, Bentwood Tavern, and Shady Creek Winery were a huge hit with my friends and I. I couldn't recommend this area and this house more for a wonderful weekend getaway or for a longer stay as well. Trevor was super friendly and responsive to all of my questions, even late into the night. Overall, great stay!

Cottage near Hagar Beach Pet friendly with Hot tub
The house was as described and pictured. We had a wonderful weekend. Enjoyed the hot tub both nights. Towels for the hot tub were provided. The house had everything we needed. Close to several great beaches and hiking areas! Comfortable beds and furniture. Very clean.

Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.
The lake house was beautiful and very relaxing, it was everything we were looking for, definitely looking to book again in summer! Very responsive and helpful host, had an amazing private chef and the views are amazing!

Hot tub! Red Tin Cottage of Harbor Country!
My stay with kate was perfect. The space was clean and exactly as described. The kitchen was stocked with everything we needed for cooking. The hot tub and yard were great additions to our stay. The neighborhood was quiet, making for a very relaxing stay. I recommend this spot for all, perfect for a girls trip or a family getaway. Plus, the hosts were incredibly accommodating!!

J’s Beach House: Hot Tub & short walk to beach!
Jen was so sweet, messaged back right away and gave us a list of things to do while we were there on a mini vacation visiting family. Hot tub and deck so clean, amazing and private Thank you and Happy holidays.

Blueberry Fields/ House and Retreat
My fiancé and I visited Donna’s place over a summer weekend, and we had the most amazing time. Donna’s house is so beautiful and welcoming - we felt at home. Her place was clean and is filled with the most thoughtful decor. It has everything anyone needs for a peaceful, relaxing stay. She was responsive right from the day of booking to our final day and even stopped by to meet us in person. We look forward to staying at her house again soon!

Michiana Cottage
Lovely Spacious, comfy place with a perfect back yard, loved the Hot tub! Great location, very serene and woodsy while so close to two great cities. Great girls weekend Getaway!
Pet-friendly cottage rentals

Northwind Llama retreat 'Loft Cottage'
We had a lovely stay at NWL. It was just the holiday break we needed! Cozy living quarters, full kitchen, a pasture full of beautiful llamas and a couple very sweet doggos. Can't wait to come stay again! Highly recommend!

Elephant Walk- Cottage 5
I've been staying at here every summer for six years now. We love the location, the casual lowkey ambiance, the proximity to the beach and gorgeous sunsets and the comfort of the cottages. The hosts are so easy and flexible, we couldn't imagine a summer without a visit to Elephant Walk!

New Buffalo retreat - Perfect year-round getaway!
We really enjoyed our time here. We stayed as a family of four and our dog. The house is very welcoming, clean, and comfortable. Our kids loved all the board games, and the backyard was fun for the kids and the dog, too. The living room is spacious and makes you feel right at home. This was our third Airbnb in New Buffalo, and it’s definitely our favorite! Colton and Abbey have clearly put a lot of thought and effort into making sure the house has everything you need. They are responsive and friendly hosts. We would stay here again!

"The Pines" in Union Pier: Year-round getaway
I have been renting Airbnb for years and hands down John’s house was the best house I have ever stayed at. The beds were incredible ( please tell me where you got your pillows and bedding). There was lovely screened porch and great room. Every amenity was available. It was a very special weekend and we had a front row view of many deer in the area. Thank you for being such a great host. We will be back !

DKM Cottage - 15 minute walk to Lake Michigan
What a beautiful location! Loved all the trees, beautiful yard to play games, super big fire pit, deck and grill was spotless! The inside was nice and spacious for the size. Great kitchen and bathrooms. The basement was large! We had an incredible time. Would come back for a longer vacation!

Camp Wanderlust-Cozy lodge-20 minute walk to beach
We loved our stay! Quick walk to coffee shops or the lake. Great location just a short drive from New Buffalo, Three Oaks and the other surrounding towns. We took our kids and dogs to Warren Sand Dunes State Park (also only a 15 minute drive) which was the highlight of the trip. We’ll be back!

Twin Cottage A- Walk to Beach & Town!
Nick and Michael were incredibly responsive and friendly and offered to help us find dog friendly spots, gave us a list of places and suggestions. The place was super cozy, clean and pleasant. The yard is awesome, totally fenced in. Despite the rain, we still had a good time and dogs had a lot of fun in the yard!

Cottage with Character
The house was perfrct for us and our dog. The binder our host left was full of great recommendations and useful instructions. The location itself is in a convenient area. Walking distance to good restaurants and shops, and short drives to wineries and the lake. The yard is huge and our dog lived running around. We appreciated the fully fenced area for her. We'd love to be back in the summer months. The only thing I would've preferred is an earlier check in.
Private cottage rentals

Cozy. Clean. Close to the beach and wineries
Our little family had a wonderful time at Valerye's place. It was very cozy and peaceful. The cottage was stocked with a ton of amenities and necessities. The location was perfect to visit all the places we wanted to go. Hagar Park is just a quick drive down the road, it is beautiful even this time of year. Would love to come back during the summer.

Barron Lake front Cottage. Notre Dame Nearby!
Great host and great place to stay while visiting the area!

Cozy Lake House with Bonus Guest Cottage!
Sandy's house was very comfortable and cute. The house has many different places places to hang out (living room, porch, fire pit area, and patio area). Each area is very peaceful. Our group had such a great time hanging out there and it was about 2-3 blocks walk to the beach. Sandy had flowers from her garden in vases for us and made us feel like we were home. We would definitely stay at Sandy's again!

Bright Beach-Community/Winter Wonderland Cottage
Louise's house is magical. I've never felt more at home in an Airbnb. The minute you open the door, you are surrounded by the beautiful colors in her gorgeous fabrics and rugs. Louise has thought of everything-from lots of towels (high humidity area and longer drying time), an incredibly well stocked kitchen, comfy beds, and lots of different seating areas and options. The screened in porch is beyond relaxing. Early mornings on the porch, listening to the birds, was my favorite way to start the day. The neighborhood beaches (15 minute walk) were private, quiet, and beautiful. Sunset at Stop 39 is the best. The beach town of New Buffalo is only a 10 minute drive, with fun rooftop restaurants and a larger beach. A farm for blueberry picking is also close by. We hope to return to Louise's again!

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.

Gram's cottage: Convenient to ND, New Buff & AWS
Jacqueline was very helpful and descriptive about everything regarding our visit. Her home felt very peaceful and is a great choice if a lake is what you are looking for. Will likely stay here again.

The White Cottage Home
This cottage was just as described. Relaxed ‘beachy’ theme. Beds were comfortable. Perfect for a weekend getaway. Enoch was a great host!!

Lonnie's Private Eco Cottage with Lake & Trails
Charming, romantic, rustic, peaceful. Cannot overstate how lovely our stay was. The cottage is just as described and provided everything we needed to have the weekend away that we wanted. Highly recommend getting out in the early morning to go deer spotting! We walked the entirety of the trails and enjoyed every bit of it. Definitely staying here again!
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- Millennium Park
- Warren Dunes State Park
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- University of Notre Dame
- The Field Museum
- Lincoln Park Zoo
- Silver Beach Carousel
- Promontory Point
- Museum of Science and Industry
- 875 North Michigan Avenue
- Skydeck Chicago
- Lincoln Park
- Adler Planetarium
- Washington Park Zoo
- Chicago Cultural Center
- Chicago History Museum
- South Bend Country Club
- Point O' Woods Golf & Country Club
- Potato Creek State Park
- Woodlands Course at Whittaker
- Culver Academies Golf Course
- Deep River Waterpark