Leelanau Peninsula Wineries Vacation Rentals

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Sep 24 - Sep 25
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Vacation Rentals in Leelanau Peninsula Wineries

Our top choices for Leelanau Peninsula Wineries vacation rentals

The Birches - Condotel in Lake Leelanau
Staircase

The Birches - Condotel in Lake Leelanau

3.5 star property
9.6 out of 10, Exceptional, (9)
"My family and I thoroughly enjoyed our stay at this beautiful, modern home. The space was clean, stylish, and had everything we needed for a comfortable and memorable visit. Although we initially had trouble accessing the unit due to unclear instructions, once we got in, everything was fantastic. We truly appreciated the peaceful atmosphere and thoughtful touches throughout. We’re definitely planning to come back! "
The Birches - Condotel in Lake Leelanau
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Exterior

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

10.0 out of 10, Exceptional, (274)
"Second time staying here and it was great again. Will definitely stay again "
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!
Highly rated 3 Bed,3 Bath, 0 cleaning fee dog friendly additional daily fee.
Outdoor dining

Highly rated 3 Bed,3 Bath, 0 cleaning fee dog friendly additional daily fee.

10.0 out of 10, Exceptional, (67)
"Matthew was an amazing host. The home is well cared for inside and out, well equipped and very clean. He had so many personal touches waiting for us. Our only regret was our stay was way too short. Thank you Matthew!"
Highly rated 3 Bed,3 Bath, 0 cleaning fee dog friendly additional daily fee.
After Dune Delight 5BR Home River Kayaks Beaches
Outdoor spa tub

After Dune Delight 5BR Home River Kayaks Beaches

9.8 out of 10, Exceptional, (26)
"Wonderful house. Perfect location"
After Dune Delight 5BR Home River Kayaks Beaches
Chic and Cozy Condo
Marina

Chic and Cozy Condo

9.6 out of 10, Exceptional, (229)
"The Condo was super clean and was as described! Within walking distance to the on site restaurants. the king-sized bed was huge and very comfortable. The condo has everything you would need for very relaxing stay in any season."
The price is ￥38,231
￥64,801 total
includes taxes & fees
Oct 19 - Oct 20
Chic and Cozy Condo
A Leland Favorite!Walk to Beach& Town Sleeps 10 OPEN for Toast the Season Wines!
On the beach, sun loungers

A Leland Favorite!Walk to Beach& Town Sleeps 10 OPEN for Toast the Season Wines!

9.8 out of 10, Exceptional, (167)
"Beautiful place, clean, walking distance to Leland."
The price is ￥36,928
￥101,330 total
includes taxes & fees
Oct 11 - Oct 12
A Leland Favorite!Walk to Beach& Town Sleeps 10 OPEN for Toast the Season Wines!
Leelanau Farmhouse Ste 1
Exterior

Leelanau Farmhouse Ste 1

9.4 out of 10, Exceptional, (16)
"close to wineries, nice shopping, and restaurants."
The price is ￥26,440
￥50,478 total
includes taxes & fees
Sep 25 - Sep 26
Leelanau Farmhouse Ste 1
Modern home in Glen Arbor. Steam shower. Walk to lake. Air conditioning.
Beach

Modern home in Glen Arbor. Steam shower. Walk to lake. Air conditioning.

10.0 out of 10, Exceptional, (49)
"Great property and location to beach for the kids"
Modern home in Glen Arbor. Steam shower. Walk to lake. Air conditioning.
Prime FALL COLOR-WINTER 2025~Spring-Summer 2026, don’t miss out, Book Today! 😄
Exterior

Prime FALL COLOR-WINTER 2025~Spring-Summer 2026, don’t miss out, Book Today! 😄

10.0 out of 10, Exceptional, (215)
"One of the best places to stay in Northern Michigan/ Sleeping Bear Dunes area. Tricia was a great host and made our stay comfortable and any issues we had she was super responsive. Great kitchen with lots of gadgets to cook great meals with. Beds were comfortable and the wood fired stove made for cozy mornings in. Location is great. Will definitely be coming back!"
Prime FALL COLOR-WINTER 2025~Spring-Summer 2026, don’t miss out, Book Today! 😄
Historic Fishtown Shanty-Renovated and Remodeled
Outdoor dining

Historic Fishtown Shanty-Renovated and Remodeled

10.0 out of 10, Exceptional, (41)
"It’s a very comfortable place on the water and walking distance to Lake Michigan. The sun sets are beautiful!! I highly recommend this place. "
Historic Fishtown Shanty-Renovated and Remodeled
New! Cute 2-bedroom cottage in quaint Northport
Outdoor dining

New! Cute 2-bedroom cottage in quaint Northport

2.0 star property
10.0 out of 10, Exceptional, (21)
"Cozy little cabin just outside Northport. Very clean, comfortable and close to dining, shopping and wineries!"
New! Cute 2-bedroom cottage in quaint Northport
The Little Green Cottage in the Woods
Beach towels

The Little Green Cottage in the Woods

10.0 out of 10, Exceptional, (41)
"Wonderful location and a beautiful home! Will definitely go back! "
The Little Green Cottage in the Woods
Riverfront condo with beach access to lake, fireplace, furnished deck & cable
Property grounds

Riverfront condo with beach access to lake, fireplace, furnished deck & cable

9.0 out of 10, Wonderful, (39)
"We really enjoyed our stay on the property. The location is wonderful!"
Riverfront condo with beach access to lake, fireplace, furnished deck & cable
Suttons Bay-Fire Pit, walk to town/beach, brewery, dining
Children's area

Suttons Bay-Fire Pit, walk to town/beach, brewery, dining

9.8 out of 10, Exceptional, (96)
"Couldn’t be in a better location. Walking distance to everything. "
Suttons Bay-Fire Pit, walk to town/beach, brewery, dining
Condo with lake views
Dining

Condo with lake views

7.6 out of 10, Good, (27)
"Condo was in a great location with fantastic views of Lake Michigan. Would rent this unit again......"
Condo with lake views
Bayfront condo with lake & bay views, deck, 2 fireplaces, private washer/dryer
Fridge, microwave, oven, stovetop

Bayfront condo with lake & bay views, deck, 2 fireplaces, private washer/dryer

9.2 out of 10, Wonderful, (26)
"The condo has lovely furniture and wonderful views! I had everything I needed for my stay in terms of bathroom and kitchen amenities. Easy check in and out."
Bayfront condo with lake & bay views, deck, 2 fireplaces, private washer/dryer
Leelanau Farmhouse - Ste 2
Property grounds

Leelanau Farmhouse - Ste 2

9.8 out of 10, Exceptional, (15)
"Comfy bed, nice remodeled bath and walkable to town"
The price is ￥23,486
￥46,904 total
includes taxes & fees
Sep 25 - Sep 26
Leelanau Farmhouse - Ste 2
Waters Edge Lakefront Cottage between Glen Arbor & Leland
On the beach

Waters Edge Lakefront Cottage between Glen Arbor & Leland

10.0 out of 10, Exceptional, (11)
"Everything was great, thanks for allowing us to stay in your beautiful cabin! Jon & Susan"
Waters Edge Lakefront Cottage between Glen Arbor & Leland
Gorgeous North Lake Leelanau frontage.
Property grounds

Gorgeous North Lake Leelanau frontage.

9.8 out of 10, Exceptional, (55)
"Wonderful stay and beautiful home!"
Gorgeous North Lake Leelanau frontage.
Upper-level condo with forest views, fireplace, soaking tub & high-speed WiFi
Property grounds

Upper-level condo with forest views, fireplace, soaking tub & high-speed WiFi

8.6 out of 10, Excellent, (32)
"As an elementary teacher ready to rest and relax- this was the perfect place!"
Upper-level condo with forest views, fireplace, soaking tub & high-speed WiFi
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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Top Leelanau Peninsula Wineries Hotel Reviews

Whaleback Inn

Whaleback Inn

10/10 Excellent
"Fanadtic place lovely owners. Clean ...beautiful gardens "
Cumbee 1-night trip
Posted 2 days ago
Whaleback Inn

Find out more about Leelanau Peninsula Wineries

Find out more about Leelanau Peninsula Wineries

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