Leelanau Peninsula Wineries Holiday Rentals

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Holiday Rentals in Leelanau Peninsula Wineries

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

9.2 out of 10, Wonderful, (22)
"We very much enjoyed this place to relax for a few nights on Lake Michigan! "
Bayfront condo with lake & bay views, deck, 2 fireplaces, private washer/dryer

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

10.0 out of 10, Exceptional, (258)
"This house is just right. We’ll-stocked kitchen, great location"
Love North Shore Cherry Cove Beachfront On West Grand Traverse Bay In Leelanau!

After Dune Delight 5BR Home River Kayaks Beaches

9.8 out of 10, Exceptional, (21)
"We were very happy with the rental unit - After Dune Delight . We had 3 1/2 families with two set of children (4). We were pleased that both the upper and lower units had fully equipped kitchens with fully stocked cabinets and all the appliances that we needed. The two levels gave us the opportunity to have some quiet time away from the larger group. The upper unit has a large table that, when opened, sits 11 people, and the lower unit has a table on the screened in porch. Unfortunately we...
After Dune Delight 5BR Home River Kayaks Beaches

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

Waterfront on Lake Leelanau & Dock Bring or Rent Boat! OPEN May 1-14

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 HK$1,940
HK$4,880 total
includes taxes & fees
30 Apr - 1 May
Waterfront on Lake Leelanau & Dock Bring or Rent Boat! OPEN May 1-14

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

9.6 out of 10, Exceptional, (216)
"As always, the perfect winter getaway. "
The price is HK$1,389
HK$2,700 total
includes taxes & fees
4 May - 5 May
Easy Entry to Chic and Cozy Condo Tucked in Wooded Dunes on Homestead Property

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

8.8 out of 10, Excellent, (26)
"It was adorable and I loved that it made me feel like I was on the set of a Golden Girls episode! Great location and great view!"
Upper-level condo with forest views, fireplace, soaking tub & high-speed WiFi

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

9.0 out of 10, Wonderful, (85)
"Great condo in a great property. We especially loved the wood burning fireplace. A cozy stay."
Glen Arbor condo in the woods w/ screened porch, A/C, washer/dryer

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

9.4 out of 10, Exceptional, (205)
"We loved it! Everything was as listed, bed was comfortable and there was an air mattress provided for a second place for someone to sleep. We did stay during the "off season" but talked about booking again "in season" when TC and Sutton's Bay are in full swing! "
Adorable studio cottage in Suttons Bay. Air conditioning. Pet friendly.

Hawks Nest Hideaway - 2 Bed 2 Bath - Screened In Deck

10.0 out of 10, Exceptional, (25)
"Wonderful condo at The Homestead! Perfect for a weekend get away of skiing and exploring Glen Arbor! The hosts were very responsive and the condo had everything we needed :) "
Hawks Nest Hideaway - 2 Bed 2 Bath - Screened In Deck

Quaint waterfront home with beach, dock, sweeping views, fast WiFi & W/D

8.4 out of 10, Very good, (11)
"The place is beautiful. Great views. But if you need to get a hold of someone, good luck! Nothing works inside the home. Shower, plugs, fans, dirty toilets. Nearly 45 degrees inside the home when we checked in. Took hours to warm the home. Unable to communicate with anyone regarding any of these issues."
Quaint waterfront home with beach, dock, sweeping views, fast WiFi & W/D

Lakefront condo with deck, gorgeous view, fireplace, & W/D

9.8 out of 10, Exceptional, (8)
"Wonderful location for all ages. Enjoyed Glen Arbor and it was easy to get to Sleeping Bear Dunes and Traverse City. We liked the condo accessibility to the beach and that it was two floors."
Lakefront condo with deck, gorgeous view, fireplace, & W/D

Perfect Sandy Beachfront, Great for Families! Stunning Sunsets and Bonfires

9.2 out of 10, Wonderful, (12)
"Great location and very quiet. Enjoyed fires at night. Especially Enjoyed the northern light display. Stayed here before and plan to again."
Perfect Sandy Beachfront, Great for Families! Stunning Sunsets and Bonfires

The Birches - Condotel in Lake Leelanau

3.5 star property
9.6 out of 10, Exceptional, (7)
"The condo is newer with plenty of space. All the basics were available (soap, utensils, laundry detergent, etc). We enjoyed walking to breakfast and a winery too. A quick drive to many other wineries and dining options. There are two sets of stairs to the top floor, but we were expecting this from the listing information. However, as another reviewer mentioned, there are fruit flies. Not just a few, probably hundreds. Our family was going out for all meals, so we did not cook there. I would not...
The Birches - Condotel in Lake Leelanau

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.

3 bed 3 bath, Outside heated pool, Close to Dunes

7.6 out of 10, Good, (5)
"The pictures do not depict the condition of the furnishings and rooms. The chairs have tears, the washing machine was falling a part, the bedroom tv had no connection, messaged the host with no response. I hate to say it but it Was not worth the cost."
3 bed 3 bath, Outside heated pool, Close to Dunes

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

9.4 out of 10, Exceptional, (30)
"during spring break when everyone heads south for the warmth, we opted for heading north and it was cold, windy and icy but so beautiful cozy and quiet….,just what we needef"
Riverfront condo with beach access to lake, fireplace, furnished deck & cable

Homestead condo, Beautifu View of Lake MI & Manitau Island, AC internet, Wi Fi

10.0 out of 10, Exceptional, (187)
"High upon a mountain. Wonderful views… very clean and owners very helpful! . "
Homestead condo, Beautifu View of Lake MI & Manitau Island, AC internet, Wi Fi

3 Bedroom-3 Bathroom Leelanau Chalet home. 0 cleaning fee and dog friendly !

10.0 out of 10, Exceptional, (50)
"Great communication, house was in great shape and well equipped. Thank you Matthew and we will be back!!"
3 Bedroom-3 Bathroom Leelanau Chalet home. 0 cleaning fee and dog friendly !

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

Leland Lodge

2.5 star property
9.2 out of 10, Wonderful, (424)
"Brian welcomed us warmly on a cold, snowy February day. He walked around the Lodge to show us where everything was. Our room was very clean and very comfortable. "
The price is HK$1,367
HK$1,450 total
includes taxes & fees
29 Apr - 30 Apr
Leland Lodge

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

After Dune Delight 5BR Home River Kayaks Beaches

9.8 out of 10, Exceptional, (21)
"We were very happy with the rental unit - After Dune Delight . We had 3 1/2 families with two set of children (4). We were pleased that both the upper and lower units had fully equipped kitchens with fully stocked cabinets and all the appliances that we needed. The two levels gave us the opportunity to have some quiet time away from the larger group. The upper unit has a large table that, when opened, sits 11 people, and the lower unit has a table on the screened in porch. Unfortunately we...
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.