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Compare 226 Vacation Homes in Leelanau Peninsula Wineries with updated reviews, rates, and availability.

Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
at the beach looking south across the deck.

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

10.0 out of 10, Exceptional, (251)
"The snow was piled up and we were nice and cozy inside our getaway. The hot tub was wonderful as we gazed up at the stars and watched the falling snow drape the trees in the forest behind the home. The view out the front was of the partially frozen Lake Michigan. The perfect getaway!!"
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
Exterior

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
In -Town Suttons Bay Walk to Beach, Near Hikes & Wineries
Ideal location in the Village of Suttons Bay. Easy walk to town and the beach.

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

10.0 out of 10, Exceptional, (136)
"My husband and I travelled to Sutton’s Bay with two other couples and our dogs, to go on a snow shoe wine tasting adventure. Our accommodations were perfect for all of us and our host was quick to respond to our questions. Her home was clean and comfortable and we had everything we needed. I would definitely come bank again! "
The price is SAR 844
SAR 2,037 total
includes taxes & fees
17 Feb - 18 Feb
In -Town Suttons Bay Walk to Beach, Near Hikes & Wineries
Cozy cottage with private pond. Close to the casino and the Bay.
Welcome to On Belanger Pond

Cozy cottage with private pond. Close to the casino and the Bay.

9.4 out of 10, Exceptional, (156)
"This was a lovely little stay. The cottage is charming and cozy. The pond out side is beautiful and serene. It is directly on a busy road as some reviews mention, but being this far out there's not much traffic at night."
Cozy cottage with private pond. Close to the casino and the Bay.
Cozy waterfront sunset cottage on Lake Leelanau. Air, Near Leland.
Enjoy amazing sunsets !

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

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
Bay View - Private Dock on West Bay

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
Dog-friendly charmer near the beach & marina - firepit, breezeway, W/D, & AC

Dog-friendly charmer near the beach & marina - firepit, breezeway, W/D, & AC

9.4 out of 10, Exceptional, (6)
"Overall good experience "
Dog-friendly charmer near the beach & marina - firepit, breezeway, W/D, & AC
White Pine Cottage- Private, Newly Built 2 miles from Leland w/ lake view!
Private kitchen

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!
Beautiful, spacious home in the village. Walk to everything. Air conditioning
Welcome to Northport Retreat !

Beautiful, spacious home in the village. Walk to everything. Air conditioning

9.8 out of 10, Exceptional, (82)
"Had a minor HVAC issue - but they were all over getting it remedied quickly. Other than that, lovely place & great time in Northport."
Beautiful, spacious home in the village. Walk to everything. Air conditioning
The Weaver House on the pristine Crystal River in Glen Arbor
Exterior

The Weaver House on the pristine Crystal River in Glen Arbor

10.0 out of 10, Exceptional, (63)
"Great house for a larger group, and you can't beat the views from the back deck. The crystal clear river is perfect for wading or boating right off the deck, and there is opportunity for plenty of wildlife sightings across the river too. The living areas are nice and open, and the dining room table is big enough for everyone! The one slight downside that's not apparent in the listing is that the layout of the rooms is a little odd. The bunk room is adjacent to the main living area, and indoor...
The Weaver House on the pristine Crystal River in Glen Arbor
After Dune Delight 5BR Home River Kayaks Beaches
Crystal-clear lakeside serenity 🌊🏡

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
Historic home near Leland. Huge porch, fire pit. Pet ok.

Historic home near Leland. Huge porch, fire pit. Pet ok.

9.0 out of 10, Wonderful, (6)
"The only complaints were the inability to lock doors (porch and kitchen entries to house) and the inability to use the pool table due to heavy mildew . wet smell"
Historic home near Leland. Huge porch, fire pit. Pet ok.
Bayside Serenity with Hot Tub! Dog Friendly!

Bayside Serenity with Hot Tub! Dog Friendly!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We stayed for a weekend in December and loved this place. We watched a meteor shower from the upstairs sitting area and loved the hot tub."
Bayside Serenity with Hot Tub! Dog Friendly!
A private ranch home on Lake Michigan with stunning sunrise views.

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
Charming Patio by the Creek, overlooking West Bay

Incredible Mid-Century Modern Waterfront Home on West Bay, on M22 - Sleeps 12

10.0 out of 10, Exceptional, (104)
"We had an awesome time at this location. Everything was very clean with plenty of necessities provided (towels, toilet paper, etc.). The kitchen was stocked with all the tools we needed to cook. Hosts left detailed instructions for checkout which we appreciated. Tons of spaces to gather and hang out, with great views of the water. Very close to wineries and restaurants, and home had ample parking. Would recommend for large groups. We had a great, fun weekend and loved the pool table!"
Incredible Mid-Century Modern Waterfront Home on West Bay, on M22 - Sleeps 12
NEW! Lake Leelanau Therapy-HotTub/Kayaks/FirePit
Aerial view

NEW! Lake Leelanau Therapy-HotTub/Kayaks/FirePit

10.0 out of 10, Exceptional, (12)
"The house is clean, huge, wonderful area around house, the nature sound makes you feel better with nice hot tub. The house has everything that need for living and its shows up care for guests! Thank you!"
The price is SAR 476
SAR 1,641 total
includes taxes & fees
17 Feb - 18 Feb
NEW! Lake Leelanau Therapy-HotTub/Kayaks/FirePit
Updated! Elizabeth House is a Charming Craftsman on Little Traverse Lake.
Exterior

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.
Close to downtown Leland, Fishtown, Vans Beach. Hot tub.

Close to downtown Leland, Fishtown, Vans Beach. Hot tub.

9.6 out of 10, Exceptional, (9)
"Great stay. Hot tub was an added bonus. Thank you! "
Close to downtown Leland, Fishtown, Vans Beach. Hot tub.
Suttons Bay farmhouse-style home. 5 bedrooms. Air conditioning. Pet okay

Suttons Bay farmhouse-style home. 5 bedrooms. Air conditioning. Pet okay

9.2 out of 10, Wonderful, (56)
"Cozy place, no kitchen towels present when we were there and no sheet "
Suttons Bay farmhouse-style home. 5 bedrooms. Air conditioning. Pet okay
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

Easy Entry to Chic and Cozy Condo Tucked in Wooded Dunes on Homestead Property
Living area

Easy Entry to Chic and Cozy Condo Tucked in Wooded Dunes on Homestead Property

9.6 out of 10, Exceptional, (216)
"Nicely decorated and super cozy - we loved the fireplace and the bed is so comfy. Never heard any noise from outside or from neighbors, very relaxing! "
The price is SAR 619
SAR 1,234 total
includes taxes & fees
1 Mar - 2 Mar
Easy Entry to Chic and Cozy Condo Tucked in Wooded Dunes on Homestead Property
The Weaver House on the pristine Crystal River in Glen Arbor
Exterior

The Weaver House on the pristine Crystal River in Glen Arbor

10.0 out of 10, Exceptional, (63)
"Great house for a larger group, and you can't beat the views from the back deck. The crystal clear river is perfect for wading or boating right off the deck, and there is opportunity for plenty of wildlife sightings across the river too. The living areas are nice and open, and the dining room table is big enough for everyone! The one slight downside that's not apparent in the listing is that the layout of the rooms is a little odd. The bunk room is adjacent to the main living area, and indoor...
The Weaver House on the pristine Crystal River in Glen Arbor
Glen Arbor condo in the woods w/ screened porch, A/C, washer/dryer
Living area - Living area

Glen Arbor condo in the woods w/ screened porch, A/C, washer/dryer

9.2 out of 10, Wonderful, (81)
"My only concern is the safety of the steps I had to navigate to and from the condo. There were railings for some of the steps, but not all, and those were scary. I'm 76 and not nearly as steady or confident as I used to be. I took my walking sticks and that's how I navigated the rail-less steps. These are only 2 or 3 steps long, but with no railing to steady me, they are a horrifying fall risk. I brought the sticks so that I could hike up and down dunes on my way to the lakeshore. I used them to...
Glen Arbor condo in the woods w/ screened porch, A/C, washer/dryer
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.