Holiday Homes in Leelanau Peninsula Wineries

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Featured Holiday Homes in Leelanau Peninsula Wineries

Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Outdoor dining

Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!

10.0 out of 10, Exceptional, (248)
"Enjoyed our stay. Nice and quiet in the winter vs. summer I’m sure. But that’s exactly what we were looking for. Thanks, Aaron. Cheers! Rich & Victoria"
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
In -Town Suttons Bay Walk to Beach, Near Hikes & Wineries
Exterior

In -Town Suttons Bay Walk to Beach, Near Hikes & Wineries

10.0 out of 10, Exceptional, (135)
"We rented this house for the weekend because we were visiting for the Toast the Season Wine Event. This house was amazing and accommodated everything we needed for the weekend!"
In -Town Suttons Bay Walk to Beach, Near Hikes & Wineries
Spacious Lake Leelanau Home on Lake Michigan!
TV, fireplace, books

Spacious Lake Leelanau Home on Lake Michigan!

9.6 out of 10, Exceptional, (4)
"This home lives up to is VRBO billing. Great place. You will love it. Lots of room; amazing deck for sunset views; close to many interesting places. Clean. Well equipped kitchen. We were very happy with our week there."
Spacious Lake Leelanau Home on Lake Michigan!
Charming cottage with shared beachfront on Grand Traverse Bay near Northport.
On the beach

Charming cottage with shared beachfront on Grand Traverse Bay near Northport.

9.4 out of 10, Exceptional, (95)
"It was very nice. Close to the water. Beautiful grounds. Will return again."
Charming cottage with shared beachfront on Grand Traverse Bay near Northport.
Gorgeous North Lake Leelanau frontage.
Pool

Gorgeous North Lake Leelanau frontage.

9.8 out of 10, Exceptional, (44)
"Really enjoyed the large deck and firepit area. Ample seating in both places and eating breakfast and having coffee on the deck was fantastic! Wonderful views of the lake!"
Gorgeous North Lake Leelanau frontage.
House on sandy beach in Omena. Budget friendly. Pet ok. Sunrise views.
On the beach

House on sandy beach in Omena. Budget friendly. Pet ok. Sunrise views.

7.6 out of 10, Good, (86)
"The house was a perfect getaway. It's a super quiet and peaceful area. My favorite part was having my coffee on the beach every morning. The house itself is a little outdated but everything is fully functional. There's enough space for everyone to stay comfortably and not be on top of each other. We were able to be secluded in a bedroom if needed and all hangout together in the livong spaces when we wanted to. I especially loved the locking gate on the deck stairs so we could hangout on the deck...
House on sandy beach in Omena. Budget friendly. Pet ok. Sunrise views.
Aaron's Fun House
Aerial view

Aaron's Fun House

10.0 out of 10, Exceptional, (17)
"Excellent location, amazing host. "
Aaron's Fun House
White Pine Cottage- Private, Newly Built 2 miles from Leland w/ lake view!
Terrace/patio

White Pine Cottage- Private, Newly Built 2 miles from Leland w/ lake view!

10.0 out of 10, Exceptional, (12)
"Property is as photographed and described, but even BETTER! Owner pride and craftsmanship on display here, with an eye for decorating and personal seasonal touches make this such a cozy retreat. Heated floors in primary bedroom and bath such a treat as the temperature dropped, and the gas fireplace in the living room removed the chill immediately. Exceeded every expectation!"
White Pine Cottage- Private, Newly Built 2 miles from Leland w/ lake view!
Bay View - Private Dock on West Bay
Property grounds

Bay View - Private Dock on West Bay

9.8 out of 10, Exceptional, (19)
"We had a fantastic weekend retreat wine tasting in Leelanau peninsula shopping downtown and the state hospital shops. The resort was comfortable and very accommodating with kitchen and laundry supplies, wood for the fireplace and Beach chairs, and fun games outside. The only concern we have was the traffic in the morning starting at 6:00 AM from the front road. It wasn’t ideal location for wineries and downtown Traverse City."
Bay View - Private Dock on West Bay
Village home in Suttons Bay. Walk to everything. Air, Grill, WIFI
Fridge, microwave, oven, stovetop

Village home in Suttons Bay. Walk to everything. Air, Grill, WIFI

9.2 out of 10, Wonderful, (44)
"Space was great - centrally located, plenty of space for the kids and cozy yard. We enjoyed our stay and will be back again!"
Village home in Suttons Bay. Walk to everything. Air, Grill, WIFI
Lodge-style multi-level home at the Homestead in Glen Arbor. Deck with grill.
Smart TV, fireplace, DVD player

Lodge-style multi-level home at the Homestead in Glen Arbor. Deck with grill.

9.6 out of 10, Exceptional, (45)
"Very cool layout. Most everything was in great shape. Beautiful location. Lots of windows....felt like we were in the middle of the woods"
Lodge-style multi-level home at the Homestead in Glen Arbor. Deck with grill.
Cozy waterfront sunset cottage on Lake Leelanau. Air, Near Leland.
Beach

Cozy waterfront sunset cottage on Lake Leelanau. Air, Near Leland.

9.6 out of 10, Exceptional, (44)
"We booked this last minute and we were so glad we did. Easy day trips to Suttons Bay, Leland and Sleeping Bear Dunes. The lake by the house was world’s largest kiddie pool…clear water, great for kids, great for swimming and we loved the kayaks and beautiful sunsets. House was well stocked (minus a hairdryer) and we had a wonderful trip! There were 5 of us and it was a perfect size!"
Cozy waterfront sunset cottage on Lake Leelanau. Air, Near Leland.
Luxury Waterfront Log Home 15 min from Traverse City w/ Dock
TV, fireplace, DVD player, table football

Luxury Waterfront Log Home 15 min from Traverse City w/ Dock

10.0 out of 10, Exceptional, (9)
"What a wonderful place. The home is beautiful inside and out. Fantastic views of the bay. Everything we needed to enjoy the weekend, celebrating our son’s ole mission peninsula wedding. We’ll definitely be back!!"
Luxury Waterfront Log Home 15 min from Traverse City w/ Dock
A private ranch home on Lake Michigan with stunning sunrise views.
Beach

A private ranch home on Lake Michigan with stunning sunrise views.

8.4 out of 10, Very good, (22)
"This is a modest 3-bedroom ranch home with a scenic Grand Traverse Bay shoreline sitting among acres of splendid Pine, Maple and Birch Forest. A generous amount of very nice lawn chairs are situated in the yard for viewing sunrises and sitting around a small fire pit. A nice 10 step staircase descends to a private natural coastline that is spectacular. Inside the home is bright, tidy and attractive. Window views are picturesque. Beds and furniture are clean and comfortable but larger beds...
A private ranch home on Lake Michigan with stunning sunrise views.
Incredible Mid-Century Modern Waterfront Home on West Bay, on M22 - Sleeps 12
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, (102)
"We just spent Thanksgiving week here with our extended family. The home was so spacious and cozy, and incredibly clean. It had everything we needed. It dumped snow and was so pretty looking over the lake - I can imagine it's glorious in summer. We had a wonderful time! "
Incredible Mid-Century Modern Waterfront Home on West Bay, on M22 - Sleeps 12
The Cherry Hill House
Fridge, microwave, oven, stovetop

The Cherry Hill House

10.0 out of 10, Exceptional, (18)
"Overall a great winter stay at the Cherry Hill house. Perfect quiet location to get to wineries, Sleeping Bear, Suttons Bay, Leland. House was clean and has everything needed. Plenty of space for 2 families with a dog. We would recommend to anyone looking for a nice spot in Leelanau county. "
The price is AU$1,066
includes taxes & fees
13 Jan - 14 Jan
The Cherry Hill House
Tree House in The Homestead
Fridge, microwave, oven, stovetop

Tree House in The Homestead

10.0 out of 10, Exceptional, (11)
"We had a great stay! Thanks "
Tree House in The Homestead
Charming Horse Farm Country Cottage on Rolling Hills
1 bedroom, iron/ironing board, free WiFi, bed sheets

Charming Horse Farm Country Cottage on Rolling Hills

10.0 out of 10, Exceptional, (229)
"Great location, quaint setting & easy access to TC, Leland, Suttons Bay."
Charming Horse Farm Country Cottage on Rolling Hills
Bear Feet Retreat Sum
Dining

Bear Feet Retreat Sum

10.0 out of 10, Exceptional, (5)
"First of all our entire group had a wonderful time at this lovely property. The manager, Katy, was outstanding and was very responsive to our needs. We did have two suggestions that might improve the stay. Our group included some elderly adults with balance and walking issues. The backyard had some lovely but for seniors challenging natural stones steps that were hard to navigate. Handrails would be helpful. Also the back patio would have been improved with a screened area to control the...
Bear Feet Retreat Sum
Updated! Elizabeth House is a Charming Craftsman on Little Traverse Lake.
Sun-loungers, beach towels

Updated! Elizabeth House is a Charming Craftsman on Little Traverse Lake.

10.0 out of 10, Exceptional, (5)
"Stayed here with my wife and 2 boys (7 and 9) and two other families, kids ranged infant-10. Beautiful property, as advertised. Very happy with the hosts and our stay!"
Updated! Elizabeth House is a Charming Craftsman on Little Traverse Lake.
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.
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Other property types in Leelanau Peninsula Wineries

Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Outdoor dining

Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!

10.0 out of 10, Exceptional, (248)
"Enjoyed our stay. Nice and quiet in the winter vs. summer I’m sure. But that’s exactly what we were looking for. Thanks, Aaron. Cheers! Rich & Victoria"
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Center of Leelanau Cty. FALL Weekends Extended Winter Stay, Short Trm Summer '25
Aerial view

Center of Leelanau Cty. FALL Weekends Extended Winter Stay, Short Trm Summer '25

9.6 out of 10, Exceptional, (102)
"Jim is wonderful to work with. Very kind and great communication. House was perfect for our stay. Thank you again and we will be back for sure!"
Center of Leelanau Cty. FALL Weekends Extended Winter Stay, Short Trm Summer '25
After Dune Delight 5BR Home River Kayaks Beaches
Beach nearby

After Dune Delight 5BR Home River Kayaks Beaches

9.8 out of 10, Exceptional, (19)
"We gather our children together for my husband’s birthday each year and travel to a destination up north for a long weekend away. The house is as listed, nestled in a quaint spot in the woods just outside Glen Arbor city limits. Lots of extra touches were inside the home to make our stay more comfortable. There were extra toiletries, coffee, coffee filters, and tea in both kitchens. The house was clean with the exception of some pet hair, and it wasn’t that big of an issue. It did describe the...
After Dune Delight 5BR Home River Kayaks Beaches
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.