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

Charming Cottage on the Lake
The cottage was beautiful, and though there was a little bit of miscommunication, Tim and Kate went above and beyond to come up with a solution for us! We would definitely consider staying again when it's warmer out!

The Cottage of Harbor Country - Close to it all!
Wow, what a gem! This place was charming, spacious, neat, with a great backyard and conveniently situated within 15 minutes of anything you could need or want. This is not your bare minimum cut and paste Airbnb—the beds and pillows were incredibly comfortable and luxurious, the decor was unique, the space was toddler friendly, and the kitchen was very well stocked. A great stay for a group overall, we’ll be back!

The Lemonade Cottage, New Buffalo. Walk to beach!
We loved our stay! The cottage was so cute and very clean. It is in a residential area, but still feels very private. The neighborhood was quiet. The outside/backyard area is amazing. We could walk everywhere (restaurants, shops, beach, market, etc…). We did not get into our car once from when we parked it until we left. Nancy was so nice to work with. She called us on our way there to let us know the hot tub motor was not working. That was not a big deal us, but she was proactive in telling us and she had it fixed by the next day. We would 100% recommend staying here and might book it again ourselves.

Cottage near Hagar Beach Pet friendly with Hot tub
Great place to stay located right in the coast and close to fun towns. Lee is an amazing host!

Cozy, Quiet Cottage with so much Character! Clean!
As soon as we started packing we already miss it we loved it the hot was nice I love how at night time the sitting area light up up the inside was lovely I love how it’s small but it have a lot of space the was our first time getting an Airbnb and we loved it 10/10 would definitely come here again food spot little far out but we didn’t mind it the drive is nice and peaceful I love how we get to cows and horses on the way only 2 things I’ll say about the Airbnb I wouldn’t complain about or make it a big deal you will see ants ofc and the bed was uncomfortable but we really didn’t mind it we had to much fun to even worry about other than that we loved it❤️

Hot tub! Red Tin Cottage of Harbor Country!
We had a quick two night stay while visiting the area. The house was as listed and we had a great time. We loved the hot tub and the indoor space. Comfortable seating in the living area while we waited out the rain. There is a train that travels close by but otherwise had a great stay!

Blueberry Fields/ House and Retreat
Very peaceful to stay put here--bring what you need and stay in these beautiful surroundings among birds and gardens and an art-filled home. Or spend time on nearby beaches and trails, wander the nearby small-town shops and nice variety of restaurants and look forward to a hot tub soak and campfire. Donna's home is welcoming and inspiring!

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
Pet-friendly cottage rentals

Comfortable, charming vintage 2 bed/1 bth cottage
We loved our winter stay here with our dog. Fran thought of everything from extra blankets to dog waste bags! We wanted for nothing & loved the short walk to the main strip of town. Beds were comfortable, everything was exceptionally clean, the fenced yard was great for the dog, and communication with host was very responsive. We highly recommend this charming cottage for any time of the year. We will definitely stay here again!

Dog-Friendly Farmhouse | 1+Acre near Lake Michigan
Third time staying here - we love this place. Brendon and Bryndal do an amazing job communicating and their place is always clean and in great shape. We like the walking areas near the house for our pup and the disc golf in Michigan City. Always a pleasure to visit - thanks

Elephant Walk- Cottage 5
The neighborhood is adorable and the easy approach to the beach makes this great for little kids and older adults. I appreciated being able to bring my pup and the fenced-in yard allowed me to relax in the Adirondack chair while she safely explored. I tried Seedz Brewery in town, and 2 in New Buffalo, as well as dined at Cafe Gulistan (-(-(all great experiences) and just really enjoyed a peaceful R&R weekend. I look forward to returning someday!

Vintage Romance Finds Cozy Charm at Depot Cottage
Very cozy and cute place! I loved the short walk into town. It was the perfect place to spend the weekend. My family & fur-baby adored this place and I definitely plan to come back. I loved the backyard! It’s so big! It was fun to hang back there and exercise. I have so many good things to say.

New Buffalo retreat - Perfect year-round getaway!
Wonderful home and location! Our family loved spending time here during our stay in new Buffalo. The yard was perfect for our dog. Colton and Abbey were terrific hosts.

Twin Cottage B- Walk to Beach & Town!
Another fantastic stay at this place! And they upgraded the mattresses so we had such a comfortable sleep both nights! This is the best airbnb in new Buffalo! We love it!!!

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!

Water's Edge Escape
Review..... Host Annette was very accommodating and fast response. The home is a very quaint cottage with every amenity we needed. There are many water toys (peddle boat, kayak, paddle board) and life jackets. My grandchildren enjoyed fishing and swimming. But, the best part is the amazing view. Even saw a deer in the lake! This place is on the top of my list when I come back. Jill St Petersburg, FL
Private cottage rentals

Family Friendly Private Beach Home New Carlisle
Great place to stay, right on the beach, comfortable.

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!

Cozy 2 bedroom cottage steps from Lake Michigan
Super comfortable place to crash. Convenient to all the activities in New Buffalo. Local golf course is super casual. Good place to take the family.

Lakefront A-Frame - Beach, Kayaks & Pontoon Rental
We choose Trevah’s place for our family weekend getaway. It was fun. My granddaughter enjoyed the spacious home. She answered our questions in a timely manner and was helpful getting us connected with the Marina to rent a pontoon for the day. Our family had a blast. The one thing that we all had to get used to was the lack of window shades, specially for the sunrise. Don’t get us wrong. We loved all the windows. But it was something to get used to. Definitely would will consider coming back. Thank you Trevah for sharing your home with us. Otherwise lovely home.

Modern Michigan Cottage
The place was a lovely little house on a beautiful, peaceful property. Everything went great. When I asked for help to adjust the A/C temperature, I got a response within minutes.

Cottage Getaway near Dunes & Lake MI w/Fire Pit
We loved our stay! This house a bigger than it seems in the photos. Spacious living room perfect for spending time together after a day of walking the trails. Chris was a great host, always communicating and quick to respond to a message. Would definitely stay again.

Blue Haven Lake Cottage
Such a cute place in such a cute town! Tons of restaurants, breweries, beaches, and shops. House was in a peaceful part of town which we loved. Had all listed amenities and was very clean! Would highly recommend!!

Cheerful 2 bedroom cottage with vintage vibes!
Jan’s place is fantastic! The place is immaculate and cozy. We especially loved all of the little details she thought of. Walking distance to restaurants and shops and a few miles to the beach. Private back patio was very nice. Jan checked on us through the trip and was very easy to work with. I definitely recommend you check out this spot.
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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
- Lincoln Park
- Museum of Science and Industry
- Willis Tower
- Lincoln Park Zoo
- Washington Park Zoo
- Potato Creek State Park
- Chicago Cultural Center
- Adler Planetarium
- Chicago History Museum
- Silver Beach Carousel
- Promontory Point
- Deep River Waterpark
- Culver Academies Golf Course
- DuSable Museum of African American History
- Museum of Contemporary Art Chicago