Leelanau Peninsula Wineries Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Leelanau Peninsula Wineries

Sugarloaf Chalet 3BDR Loft 2510
3.0 star property
9.0 out of 10, Wonderful, (2)
"The pictures of this property do not do it justice! This cute, super clean mid century modern chalet has everything you could ever need. The beds were super comfortable, the main spaces for gathering were inviting and cozy. The views out each window are a visibly stunning green space. There is easy access to all the wineries in the area. I would definitely stay there again."
United States
Pamela
The price is AU$747
includes taxes & fees
28 Oct - 29 Oct
Sugarloaf Chalet 3BDR Loft 2510
Lime Lake Therapy-Hot Tub/Fire Pit/Ping-Pong/AC
9.8 out of 10, Exceptional, (21)
"Great location, great property."
United States
J P.
Lime Lake Therapy-Hot Tub/Fire Pit/Ping-Pong/AC
Come cozy up next to the fireplace at our contemporary condo centrally located
10.0 out of 10, Exceptional, (45)
"Wonderful place with great hosts! Would definitely stay here again "
United States
Kristopher P.
The price is AU$589
includes taxes & fees
28 Oct - 29 Oct
Come cozy up next to the fireplace at our contemporary condo centrally located
Leelanau condo on golf course close to beaches, wineries, sand dunes, and more
10.0 out of 10, Exceptional, (125)
"Wonderful condo with great accommodation's. Location was perfect for golf, lakes, and wonderful restaurants."
United States
Marie M.
Leelanau condo on golf course close to beaches, wineries, sand dunes, and more
Leelanau Farmhouse Ste 2
9.4 out of 10, Exceptional, (19)
"We had a wonderful time…three wineries and restaurants within walking distance…very clean annd well equipped (great coffee)…loved the front porch…would definitely come back again!"
United States
Mark
The price is AU$397
includes taxes & fees
28 Oct - 29 Oct
Leelanau Farmhouse Ste 2
Studio in Lake Leelanau with outside entrance, king bed, & WiFi
8.8 out of 10, Excellent, (9)
"Loved it"
United States
marcy B.
The price is AU$420
includes taxes & fees
10 Nov - 11 Nov
Studio in Lake Leelanau with outside entrance, king bed, & WiFi
A Leland Favorite!Walk to Beach& Town Sleeps 10 OPEN 1st Toast the Season Wines!
9.8 out of 10, Exceptional, (169)
"Easy walk/bike ride to beach and town. Plenty of rooms, grilled multiple nights. Would stay again next time!"
United States
Molly L.
The price is AU$1,066
includes taxes & fees
28 Oct - 29 Oct
A Leland Favorite!Walk to Beach& Town Sleeps 10 OPEN 1st Toast the Season Wines!
🏡 Sugarloaf Chalet – Pet Friendly Escape | Hot Tub • Fireplace • Loft • Bar Area ➠ 2510
8.4 out of 10, Very good, (6)
"The property location was great! Really close to many Leelanau wineries and Suttons Bay. The amenities were nice, especially in the kitchen."
United States
Heather G.
The price is AU$1,237
includes taxes & fees
28 Oct - 29 Oct
🏡 Sugarloaf Chalet – Pet Friendly Escape | Hot Tub • Fireplace • Loft • Bar Area ➠ 2510
The Leland Blue on M-22
10.0 out of 10, Exceptional, (13)
"This is such a cute, clean place to stay and oh so comfortable! Everything was stocked well and the outdoor area is nice along with the front porch. We enjoyed everything about it!"
United States
Angie H.
The price is AU$530
includes taxes & fees
3 Nov - 4 Nov
The Leland Blue on M-22
Chic and Cozy Condo
9.6 out of 10, Exceptional, (230)
"Excellent accommodations excellent. Beach access is difficult through private areas. "
United States
James K.
The price is AU$522
includes taxes & fees
2 Nov - 3 Nov
Chic and Cozy Condo
The Cherry Hill House
10.0 out of 10, Exceptional, (19)
"The property was clean and comfortable"
United States
James G.
The price is AU$1,006
includes taxes & fees
28 Oct - 29 Oct
The Cherry Hill House
Leelanau Day Tripper - Modern Barndominium Retreat | Sauna • Bikes • Beaches • W
10.0 out of 10, Exceptional, (1)
"We had a wonderful weekend at this beautiful place. Robin replied the message extremely fast, and they even provide a cage for our dogs and it save us a lot of time to settle our pets. The rooms are wonderful and really comfy. I love how they designed their kitchen, it looks wonderful. We started a pit fire in the night and the wood was provided right next to the pit. Its really convenient! I would definitely come visit again!"
United States
Chenwei W.
The price is AU$1,181
includes taxes & fees
5 Nov - 6 Nov
Leelanau Day Tripper - Modern Barndominium Retreat | Sauna • Bikes • Beaches • W
Stunning views! 2 king bdrms w private bathrooms. Walk to Lake Michigan beach!
9.4 out of 10, Exceptional, (37)
"Super friendly host at a great location. A great place to stay if you love to wake up to views of lake Michigan."
United States
Kyle F.
Stunning views! 2 king bdrms w private bathrooms. Walk to Lake Michigan beach!
Feet from Lake & Downtown, Pond View, Hot Tub, Pet Friendly, Firepit,6BR/4Floors
10.0 out of 10, Exceptional, (11)
"We absolutely loved the house and the town of Northport for our long weekend stay! It was the perfect location to enjoy the fall colors and everything the town has to offer. The location makes it easy to walk to anything in town and the house itself was well appointed and overall a great experience. Would definitely recommend to anyone looking to visit Northport! "
United States
Ethan H.
The price is AU$963
includes taxes & fees
29 Oct - 30 Oct
Feet from Lake & Downtown, Pond View, Hot Tub, Pet Friendly, Firepit,6BR/4Floors
Leelanau Farmhouse - Ste 2
9.8 out of 10, Exceptional, (16)
"We enjoyed or stay cute little place just like pictures. Our host Natalie was amazing very easy to talk to an assisted us with anything we needed, as soon as we needed. Would definitely stay at her place again."
United States
Kelly N.
The price is AU$417
includes taxes & fees
28 Oct - 29 Oct
Leelanau Farmhouse - Ste 2
The Dexter by Kasa
2.0 star property
9.8 out of 10, Exceptional, (30)
"It was really nice and well decorated!"
United States
Heidi
The price is AU$252
includes taxes & fees
28 Oct - 29 Oct
The Dexter by Kasa
Pinestead Reef Resort
4.0 star property
8.6 out of 10, Excellent, (567)
"We had a great stay. It was relaxing and comfy"
United States
Leoma L
The price is AU$152
includes taxes & fees
28 Oct - 29 Oct
Pinestead Reef Resort
The Shores Lake View Condo Unit 5681
2.5 star property
9.6 out of 10, Exceptional, (7)
"Spend my Birthday there and I will definitely go back there, so clean and peaceful."
United States
Diamond
The Shores Lake View Condo Unit 5681
The Flat by Wanderlust Abodes
3.5 star property
9.6 out of 10, Exceptional, (5)
"We enjoyed the stay at The Flat very much. Will gladly come again."
United States
Waclaw
The price is AU$263
includes taxes & fees
25 Nov - 26 Nov
The Flat by Wanderlust Abodes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Leelanau Peninsula Wineries Hotel Reviews

Find out more about Leelanau Peninsula Wineries

Everything you need to know about Leelanau Peninsula Wineries holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Leelanau Peninsula Wineries holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leelanau Peninsula Wineries holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Leelanau Peninsula Wineries holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leelanau Peninsula Wineries. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leelanau Peninsula Wineries holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leelanau Peninsula Wineries holiday rentals we have selected for you start as low as AU$522 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Leelanau Peninsula Wineries rentals

At Expedia, we put the best Leelanau Peninsula Wineries holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Leelanau Peninsula Wineries rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leelanau Peninsula Wineries holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leelanau Peninsula Wineries. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.