
Cottage holiday rentals in Lakeside
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Lakeside
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Lakeside
Cottage rentals with a hot tub

Cozy Cottage Steps to Beach, Pool, Hot Tub & More
This was such a beautiful and relaxing weekend getaway for my friend and I and our pups. The cottage was so cozy, more spacious than expected, and very well maintained. Frank was great at communicating the house rules and everything was laid out clearly. It was clearly off-season for Lakeside because the area was very quiet which was a big bonus for us. We enjoyed some long walks with the dogs and took them to the beach in the evenings to see the sun go down. We also enjoyed soaking in the hot tub and working on the puzzle at the cottage. Would love to come again soon! Thank you Frank!

Casa Playa New House in Union Pier w/ Private Spa
This is a great place, exactly as advertised. We loved the hot tub and all the fun stuff to do nearby.

Heated pool & private hot tub!
We had a great stay! Great location, near New Buffalo and Union Pier attractions. The house was very clean and comfortable. Plenty of space for our group. The back patio was perfect, a lot of seating and the hot tub. We’ll look to stay here again next time we’re headed to New Buffalo

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.

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!
Great place to stay and the local area was absolutely gorgeous! We definitely appreciated how the host provided a binder full of local restaurants, instruction manuals, and places to visit! Not to mention, heated bathroom flooring was life changing! Thank you again ♥️

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!

Perfect Get Away - Private Hot Tub - Lots of Room
We loved staying in this adorable lake house in New Buffalo! It's a perfect location and is within walking distance of many restaurants, coffee shops, and the beach! This house was ideal for a large group and housed 10 adults and 3 children comfortably. I would definitely recommend staying here if you're planning on coming to New Buffalo!
Pet-friendly cottage rentals

Northwind Llama retreat “Loft Cottage”
On our way home I said to my wife that this place is what you always _hope_ an Airbnb is gonna be like but almost never is. Robert was friendly without being overbearing and even recommended and excellent local restaurant. The farm setting was lovely, and the llamas and dogs were great company. The location is perfect, there's lots to see just minutes away. We will definitely be back and we're recommending the place to our friends and family as well!

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!

Family friendly new house in woods /great for kids
Yes and yes!! We loved our stay at Anna’s place. From the treehouse to the glass windows to the ease of use - this was a great spot for our family of 5 Fall getaway. My 7 year old just kept saying Can it get any better?! We loved it..:.Thank you!

Camp Wanderlust-Cozy lodge-20 minute walk to beach
Only stayed at this house for 2 nights but wish it could have been longer. We loved the house. it is very quaint, comfortable and in a great location! Plenty of room with 3 bedrooms and the beds were very comfortable which is a key attribute that is very important to me. We would definitely stay here again!

Twin Cottage A- Walk to Beach & Town!
We were extremely happy with the AirBnB. Nick and Michael were very proactive with reaching out and had a binder at the place with recommendations and check out instructions. If we come back to New Buffalo with 4 people we would look at booking this place again. It was a great experience.

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!

Summer Dates April 15 - Beach Cottage 3 beds
This was a darling home with a lot of nostalgic elements and vintage touches. It was perfect for our Mom-and-grown-kids-reunion. The kitchen is small, and not conducive to large meals, but was fine for quick-preparation meals and had pretty much everything we needed (including a quality cookie sheet.) We did wish there was air conditioning, but we managed with the really nice ceiling fans and floor fan.

Elephant Walk- Cottage 4
Erica and Fred are amazing hosts! We frequent this area and always seem to come back to Elephant Walk for the charm and memories. Our kids love the space and proximity to the beach and Red Arrow Road House. Erica and Fred are so kind and helpful. It’s easy to feel at home when you stay here. The cottage has everything you need. I highly recommend this place! Thanks guys!

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.

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.
Destinations to explore
- Downtown Chicago Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- Grand Rapids Holiday rentals
- South Bend Holiday rentals
- Holland Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- South Haven Holiday rentals
- Fort Wayne Holiday rentals
- Evanston Holiday rentals
- Chicago Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Lincoln Park
- Museum of Science and Industry
- Willis Tower
- Chicago History Museum
- Potato Creek State Park
- Chicago Cultural Center
- Promontory Point
- Washington Park Zoo
- Silver Beach Carousel
- Point O' Woods Golf & Country Club
- Skydeck Chicago
- Museum of Contemporary Art Chicago
- Maggie Daley Park
- DuSable Museum of African American History