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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
16 Feb - 17 Feb
Tomorrow
17 Feb - 18 Feb
Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar

Holiday Rentals in Leelanau Peninsula Wineries

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

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 €322
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
Property grounds

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
Fridge, microwave, oven, stovetop

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
West Bay Waterfront, Hot Tub, Swimming, Expansive Deck at All Decked Out!
Terrace/patio

West Bay Waterfront, Hot Tub, Swimming, Expansive Deck at All Decked Out!

10.0 out of 10, Exceptional, (11)
"really enjoyed this cozy house for Winter getaway. Nice upstairs with great view of the Traverse Bay, roomy downstairs as well, although we really all collected upstairs for the view. Hot tub viewing the lake was wonderful!"
West Bay Waterfront, Hot Tub, Swimming, Expansive Deck at All Decked Out!
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, (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!
6-bedroom estate in welcoming Traverse City with fitness room, WiFi, AC
Outdoor spa tub

6-bedroom estate in welcoming Traverse City with fitness room, WiFi, AC

6-bedroom estate in welcoming Traverse City with fitness room, WiFi, AC
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
Suttons Bay farmhouse-style home. 5 bedrooms. Air conditioning. Pet okay
Property grounds

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
June 2025 open, stunning sunset waterfront on N Lake Leelanau.
Property grounds

June 2025 open, stunning sunset waterfront on N Lake Leelanau.

10.0 out of 10, Exceptional, (21)
"My wife and I stayed here M-F the second week in October. We came for the fall foliage, scenic drives, wineries, cideries and relaxation in a cozy house on a lake. All boxes checked…we had a perfect week! This house had plenty of room, was well equipped and the entire rental process was flawless! "
June 2025 open, stunning sunset waterfront on N Lake Leelanau.
2 bedroom + loft near Lake Leelanau. Fire pit, W/D, WIFI
Exterior

2 bedroom + loft near Lake Leelanau. Fire pit, W/D, WIFI

9.2 out of 10, Wonderful, (9)
"The house was better than the pictures. It had everything we needed! We were a group of 5 girls on a wine tour aged 22-62. We would definitely stay here again! The only thing I would change is not leaving my white Stanley cup on the counter at checkout. There are lots of games and books for someone hanging around the house. "
2 bedroom + loft near Lake Leelanau. Fire pit, W/D, WIFI
Tasteful Glen Arbor condo with beautiful Lake Michigan views, deck & fireplaces
Beach

Tasteful Glen Arbor condo with beautiful Lake Michigan views, deck & fireplaces

9.4 out of 10, Exceptional, (23)
"The location of the condo is in the Homestead complex. The Homestead amenities lie,the pool can not be used. The condo is beautifully located towards the lake, the sunsets can be watched from the porch and are spectacular. "
Tasteful Glen Arbor condo with beautiful Lake Michigan views, deck & fireplaces
Brand New Finnish Holiday House
Sun-loungers

Brand New Finnish Holiday House

Brand New Finnish Holiday House
Lake Michigan beachfront, 2-bedroom, 2 full bath condo with cable TV and Wi-Fi.
TV

Lake Michigan beachfront, 2-bedroom, 2 full bath condo with cable TV and Wi-Fi.

10.0 out of 10, Exceptional, (68)
"We very much enjoyed our short stay. Kitchen was well equipped and common area was cozy with a fantastic view. Appreciated the deck with table and chairs too! "
Lake Michigan beachfront, 2-bedroom, 2 full bath condo with cable TV and Wi-Fi.
Classic Cottage in the Heart of Leland
Sun-loungers, beach towels

Classic Cottage in the Heart of Leland

10.0 out of 10, Exceptional, (12)
"Wonderful place and owners , can’t think of a better place to stay"
Classic Cottage in the Heart of Leland
Stunning log home near Leland with spectacular views. Hot tub. A/C.
Fridge, microwave, oven, stovetop

Stunning log home near Leland with spectacular views. Hot tub. A/C.

9.2 out of 10, Wonderful, (80)
"This log cabin was well equipped, super comfy & has spectacular views. It’s close to Leland, Suttons Bay, a beautiful beach & hiking trails. Games & puzzles for downtime too! We loved it!"
Stunning log home near Leland with spectacular views. Hot tub. A/C.
Adorable studio cottage in Suttons Bay. Air conditioning. Pet friendly.
Beach

Adorable studio cottage in Suttons Bay. Air conditioning. Pet friendly.

9.4 out of 10, Exceptional, (204)
"Very cute cottage in a great location in Suttons Bay. Short walk to docks, beach and town. We hit this at just the right time for a fall color long weekend. Definitely would recommend."
Adorable studio cottage in Suttons Bay. Air conditioning. Pet friendly.
Waterfront on Lake Leelanau with Dock “5 STARS”! Huge lawn, kayaks, ping pong

Waterfront on Lake Leelanau with Dock “5 STARS”! Huge lawn, kayaks, ping pong

10.0 out of 10, Exceptional, (128)
"Your house worked great for all of us, great setup, they only complaint was all the ice in the driveway and walk way, very slippery. "
The price is €756
includes taxes & fees
1 Mar - 2 Mar
Waterfront on Lake Leelanau with Dock “5 STARS”! Huge lawn, kayaks, ping pong
Cozy cottage with private pond. Close to the casino and the Bay.
Property grounds

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.
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
Direct Lake Leelanau Sunset view, Fire pit, grill, dock, mooring, dog ok
Exterior

Direct Lake Leelanau Sunset view, Fire pit, grill, dock, mooring, dog ok

9.2 out of 10, Wonderful, (9)
"Very private location Great View !!!!"
Direct Lake Leelanau Sunset view, Fire pit, grill, dock, mooring, dog ok
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.
Don't see what you're looking for?
See all available properties in Leelanau Peninsula Wineries
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Leelanau Sands Casino & Lodge
Exterior

Leelanau Sands Casino & Lodge

2.5 star property
8.2 out of 10, Very good, (477)
"While the hotel doesnt really have any amenities, it is clean, safe and the staff was very friendly. The one amenity the do have is a shuttle to the casino. It would be a quick walk but its great to have this option in the winter.we will definitely be back!"
Leelanau Sands Casino & Lodge
The Weaver House on the pristine Crystal River in Glen Arbor
Property grounds

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

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 €322
includes taxes & fees
1 Mar - 2 Mar
Easy Entry to Chic and Cozy Condo Tucked in Wooded Dunes on Homestead Property
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.