Search Holiday Rentals in Leelanau Peninsula Wineries

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Leelanau Peninsula Wineries

Property grounds
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
10.0 out of 10, Exceptional, (226)
"The view from the house was amazing and it’s very private and quiet. The amenities were everything you may need. Definitely top tier."
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Property grounds
The Heart of the Village
10.0 out of 10, Exceptional, (70)
"Perfect spot for those that don’t enjoy large crowds! Quiet and cute little neighborhood and still plenty to do on a cold windy rainy weekend. Lots of wine tasting! Only thing we would have enjoyed more was a TV to watch the U of M game! The pub closes at 9 in the fall! Other than that it was perfect. Clean and Karen was very attentive! We would love to come back some day!"
The Heart of the Village
Property grounds
Walk to everything from this 1 Bedroom Beach House
10.0 out of 10, Exceptional, (18)
"Nice time of year to be up there, the town was very sleepy. Enjoyed the scenery and hiking."
Walk to everything from this 1 Bedroom Beach House
Save an average of 15% on thousands of hotels when you're signed in
Sun-loungers
OPEN for Wine with A Twist! 5-STAR Waterfront Home with Dock On Lake Leelanau
10.0 out of 10, Exceptional, (112)
"This house was great for our family, lots of space to spread out, great location to get to other spots in leelanau and also traverse city. Would definitely recommend!"
OPEN for Wine with A Twist! 5-STAR Waterfront Home with Dock On Lake Leelanau
Beach
Tasteful Glen Arbor condo with beautiful Lake Michigan views, deck & fireplaces
10.0 out of 10, Exceptional, (15)
"The place was spacious with nice views out the living rooms."
Tasteful Glen Arbor condo with beautiful Lake Michigan views, deck & fireplaces
Outdoor spa tub
Stunning Home w/ Hot Tub & Lake Views!
10.0 out of 10, Exceptional, (11)
"Our children joined us for a Christmas celebration. The property was very accommodating with bedrooms for everyone. The beds were comfy with a fabulous view of the water."
Stunning Home w/ Hot Tub & Lake Views!
Exterior
Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay
10.0 out of 10, Exceptional, (98)
"Clean, cozy spot to get away. Hosts are responsive and helpful. I would definitely take their suggestion #14 on their welcome letter to the hiking trail and all the food suggestions are on par (with many walkable from cottage). This may turn into a yearly destination for us."
Quiet, Private, Waterfront - Luxury on 125 Ft. of Suttons Bay
Beach nearby
Secluded Suttons Bay Abode w/ Fire Pit, Near Lakes
10.0 out of 10, Exceptional, (2)
"We were up for a quick weekend in and around Suttons Bay. This location was comfortable and served our needs perfectly. Thanks."
Secluded Suttons Bay Abode w/ Fire Pit, Near Lakes
Exterior
Wayfarer Tree House S
10.0 out of 10, Exceptional, (3)
"Great communication about property and surrounding area. Well equipped kitchen but microwave on top of refrigerator, very high. Great fire ring outside and close walk to lake. Nice shower upstairs but also need shower downstairs as tub inaccessible for most seniors. Windows everywhere so felt we were living in the woods."
The price is £641
per night
2 May - 3 May
Wayfarer Tree House S
Beach nearby, sun-loungers, beach towels
Leelanau condo on golf course close to beaches, wineries, sand dunes, and more
10.0 out of 10, Exceptional, (81)
"There was a slight odor of pine (I think) which I found offensive because I am super sensitive to scents. It was especially annoying when trying to fall asleep. Other than that, the condo is neat & well supplied for the small condo."
Leelanau condo on golf course close to beaches, wineries, sand dunes, and more
Property grounds
Million Dollar Views: Bayshore Beach House w/ Opt. RV Pads, Beach Firepit & More
10.0 out of 10, Exceptional, (1)
"This rental property was everything we wanted and more. The views of the morning sunrise were amazing. This house had every little thing you would need. Everything was very clean and the towels were like clouds of softness. The kitchen is nicely stocked along with every other room. The bottle of champagne was a nice touch. There was plenty of wood for an outside fire but it was a little too cold for us this time of year so we skipped doing that this time. We definitely look forward to coming...
The price is £462
per night
2 May - 3 May
Million Dollar Views: Bayshore Beach House w/ Opt. RV Pads, Beach Firepit & More
On the beach, sun-loungers, beach towels
Incredible Mid-Century Modern Waterfront Home on West Bay, on M22 - Sleeps 12
10.0 out of 10, Exceptional, (88)
"This is was our second July family vacation on the beautiful shores of Lake Michigan. The lovely home accommodated our family with room to spare. We thank the owners for sharing this amazing property with us."
Incredible Mid-Century Modern Waterfront Home on West Bay, on M22 - Sleeps 12
Exterior
Super cute loft on the lake!
10.0 out of 10, Exceptional, (3)
"All I can say I cried going home"
Super cute loft on the lake!
On the beach
Beautiful beachfront condo with deck, beach views, fireplace, washer/dryer
10.0 out of 10, Exceptional, (13)
"This condo was very spacious with comfortable updated furniture. The kitchen was well supplied and functional. We appreciated the two second floor bedrooms since we had a toddler who needed naps and early bedtime. We used the fireplace and it made the living area even cozier. Beds were very comfortable! The view is as pictured - it's super. The host was very easy to reach and had excellent communication. One of our favorite floorplans in the Homestead."
Beautiful beachfront condo with deck, beach views, fireplace, washer/dryer
Outdoor dining
White Pine Cottage- Private, Newly Built 2 miles from Leland w/ lake view!
10.0 out of 10, Exceptional, (2)
"Lovely place for two, with dogs. We enjoyed this as a great base for looking around the north. Clean, charming small place to stay eith great facilities. We aim to stay there again!"
White Pine Cottage- Private, Newly Built 2 miles from Leland w/ lake view!
Property grounds
Quiet and Comfy 3 bed/2bath - Chalet w/ Hot tub
9.8 out of 10, Exceptional, (16)
"Great stay! Property was quaint, home was clean and welcoming. We absolutely loved the hot tub and used it daily. Centrally located for the peninsula."
Quiet and Comfy 3 bed/2bath - Chalet w/ Hot tub
Property grounds
Riverfront condo with beach access to lake, fireplace, furnished deck & cable
9.8 out of 10, Exceptional, (16)
"nice view"
Riverfront condo with beach access to lake, fireplace, furnished deck & cable
Property grounds
After Dune Delight 5BR Home River Kayaks Beaches
9.8 out of 10, Exceptional, (16)
"This property was home to our group of 8 golfers this past weekend. All of the guys really enjoyed the setting. Fishing from the dock. Paddling the kayaks on the Crystal River. Sitting around the campfire. Watching the big TV in the family room. Eating meals in the screened-in porch while overlooking the river. This is an expansive house with plenty of room for everyone to enjoy. Book it now. You will love it. Communication with the property manager (Dylan) was excellent. Very speedy...
After Dune Delight 5BR Home River Kayaks Beaches
On the beach, sun-loungers
Open for Wine with A Twist! In-Town Leland! Walk to Beach
9.8 out of 10, Exceptional, (140)
"We had a pleasant stay and place is cozy. We had wonderful time."
Open for Wine with A Twist! In-Town Leland! Walk to Beach
Fridge, microwave, stovetop, dishwasher
Waterfront Suttons Bay Cottage w/ Fire Pit!
9.8 out of 10, Exceptional, (8)
"We had a great stay. Check in/out was easy and the house was clean and tidy. Even though it was 15 degrees outside, there is a breakfast nook in the kitchen with a full view of the bay, and we spent a lot of time there enjoying the view. One thing to note is that the bed was quite stiff, which we didn't like."
Waterfront Suttons Bay Cottage w/ Fire Pit!
Don't see what you're looking for?
See all available properties in Leelanau Peninsula Wineries
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.

Leelanau Peninsula Wineries Holiday Rental Travel Info

Holiday rentals
55
Popular accommodation
Leelanau Peninsula Wineries private holiday homes
International airport
Traverse City, MI (TVC-Cherry Capital)

Other types of properties in Leelanau Peninsula Wineries you may be interested in

Property grounds
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
10.0 out of 10, Exceptional, (226)
"The view from the house was amazing and it’s very private and quiet. The amenities were everything you may need. Definitely top tier."
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Property grounds
After Dune Delight 5BR Home River Kayaks Beaches
9.8 out of 10, Exceptional, (16)
"This property was home to our group of 8 golfers this past weekend. All of the guys really enjoyed the setting. Fishing from the dock. Paddling the kayaks on the Crystal River. Sitting around the campfire. Watching the big TV in the family room. Eating meals in the screened-in porch while overlooking the river. This is an expansive house with plenty of room for everyone to enjoy. Book it now. You will love it. Communication with the property manager (Dylan) was excellent. Very speedy...
After Dune Delight 5BR Home River Kayaks Beaches
Exterior
Leelanau Sands Casino & Lodge
2.5 star property
8.4 out of 10, Very good, (312)
"Looking forward to our next stay!!"
The price is £83
per night
2 May - 3 May
Leelanau Sands Casino & Lodge
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.

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, apart-hotels, 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 favorite 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 depends 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 £462 per night. Entering your travel dates in the search wizard you might find 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. 

Recent reviews of Leelanau Peninsula Wineries properties
Expedia verified reviews