A vineyard with rows of grapevines supported by wooden stakes and netting.

Leelanau Peninsula Wineries Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Leelanau Peninsula Wineries vacation rentals

A modern kitchen with dark cabinets, stainless steel appliances, and a central island with two black chairs.

1. The Birches - Condotel in Lake Leelanau

The Birches - Condotel in Lake Leelanau
3.5 star property
Lake Leelanau
9.6 out of 10, Exceptional, (12 reviews)
"My family and I really enjoyed our stay. The home was clean, and the check in process was smooth."
United States
Jaspal
$599 nightly
The price is $635
Sep 1 - Sep 2
Total with taxes and fees
The Birches - Condotel in Lake Leelanau
A spiral staircase with a metal railing, a television on the wall, and a painting on the wall.

2. Chalet w Loft Near Sleeping Bear 2552

Chalet w Loft Near Sleeping Bear 2552
2.0 star property
Cedar
Chalet w Loft Near Sleeping Bear 2552
A bedroom with a large bed, two bedside lamps, a window with blinds, and a view of the outside.

3. 🌤 The Birches - Condotel Downtown Lake Leelanau Unit 4

🌤 The Birches - Condotel Downtown Lake Leelanau Unit 4
2.0 star property
Lake Leelanau
$764 nightly
The price is $810
Sep 30 - Oct 1
Total with taxes and fees
🌤 The Birches - Condotel Downtown Lake Leelanau Unit 4
A modern kitchen with dark cabinetry, stainless steel appliances, a large window, and two bar stools.

4. The Birches

The Birches
2.0 star property
Lake Leelanau
$613 nightly
The price is $650
Sep 30 - Oct 1
Total with taxes and fees
The Birches
A modern living room with a sofa, a coffee table, and a TV on a wooden stand.

5. Boardwalk Suites & Residences By Kasa

Boardwalk Suites & Residences By Kasa
2.0 star property
Downtown Traverse City
8.8 out of 10, Excellent, (170 reviews)
"Nice room and property."
United States
Nicholas
$89 nightly
The price is $99
Sep 30 - Oct 1
Total with taxes and fees
Boardwalk Suites & Residences By Kasa
A stone-arched outdoor seating area with wicker furniture and a round table, overlooking a scenic view of the sea.

6. 539 Bay St. Lake View Condo Unit 104E

539 Bay St. Lake View Condo Unit 104E
3.0 star property
Slabtown
539 Bay St. Lake View Condo Unit 104E
A modern kitchen with white cabinets, a granite countertop, and a central island with bar stools.

7. Traverse City Flats

Traverse City Flats
3.5 star property
Williamsburg
9.6 out of 10, Exceptional, (29 reviews)
"My family and I enjoyed our stay here. "
United States
logan
$1,594 nightly
The price is $1,690
Sep 16 - Sep 17
Total with taxes and fees
Traverse City Flats
A dining area with a view of the sea, a sofa, and a TV displaying the Netflix logo.

8. 539 Bay Street Traverse City - Luxury Downtown Residences

539 Bay Street Traverse City - Luxury Downtown Residences
4.0 star property
Slabtown
9.6 out of 10, Exceptional, (61 reviews)
"Great location, walkable to downtown, and the beach across the street. Check-in and Check-out were both easy and quick. Experience like a hotel, but much better priced. Property is beautiful, clean, modern, and we will be back."
United States
Chris
$553 nightly
The price is $614
Sep 28 - Sep 29
Total with taxes and fees
539 Bay Street Traverse City - Luxury Downtown Residences

9. Pinestead Reef Resort

Pinestead Reef Resort
4.0 star property
Traverse City
8.8 out of 10, Excellent, (632 reviews)
"Just great environment to be at."
United States
shane
$127 nightly
The price is $141
Sep 1 - Sep 2
Total with taxes and fees
Pinestead Reef Resort
A cabin with a stone pathway leading to a deck with benches, surrounded by trees.

10. Large Glen Lake Retreat: Private Beach & Deck

Large Glen Lake Retreat: Private Beach & Deck
3.0 star property
Maple City
$1,288 nightly
The price is $1,365
Sep 13 - Sep 14
Total with taxes and fees
Large Glen Lake Retreat: Private Beach & Deck
A stone-arched outdoor seating area with wicker furniture and a round table, overlooking a scenic view of the sea.

11. 2BDR Loft Suite Golf Course Condo 5549

2BDR Loft Suite Golf Course Condo 5549
3.0 star property
Williamsburg
10.0 out of 10, Exceptional, (1 review)
"Very clean. Felt very comfortable. Would recommend especially for golfers. "
United States
Kelly
$576 nightly
The price is $610
Sep 21 - Sep 22
Total with taxes and fees
2BDR Loft Suite Golf Course Condo 5549
A coastal property with a swimming pool, beach, and pier extending into the water.

12. 2 Bedroom Condo Golf Course Views 5166

2 Bedroom Condo Golf Course Views 5166
3.0 star property
Williamsburg
9.0 out of 10, Wonderful, (4 reviews)
"Good stay"
United States
junghwan
$514 nightly
The price is $545
Sep 8 - Sep 9
Total with taxes and fees
2 Bedroom Condo Golf Course Views 5166
An outdoor patio with stone arches, wicker furniture, and a view of the sea.

13. 4BDR Retreat Downtown & East Bay 3191

4BDR Retreat Downtown & East Bay 3191
3.0 star property
Traverse City
$683 nightly
The price is $724
Sep 23 - Sep 24
Total with taxes and fees
4BDR Retreat Downtown & East Bay 3191
A coastal property with a swimming pool, beach, and pier extending into the water.

14. The Shores Grand Traverse Bay Unit 5704

The Shores Grand Traverse Bay Unit 5704
3.0 star property
Williamsburg
2.0 out of 10, (1 review)
$589 nightly
The price is $622
Sep 4 - Sep 5
Total with taxes and fees
The Shores Grand Traverse Bay Unit 5704
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

15. The Loop Downtown By Kasa

The Loop Downtown By Kasa
4.0 star property
Downtown Traverse City
9.0 out of 10, Wonderful, (37 reviews)
"Very convenient location. Walking distance to everything. Place was clean!"
United States
Roy
$160 nightly
The price is $178
Sep 1 - Sep 2
Total with taxes and fees
The Loop Downtown By Kasa
A stone-arched outdoor seating area with wicker furniture and a round table, overlooking a scenic view of the sea.

16. Lakeview Golf Retreat 1BDR Condo 5057

Lakeview Golf Retreat 1BDR Condo 5057
3.0 star property
Williamsburg
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful property "
United States
Erica
$353 nightly
The price is $374
Sep 21 - Sep 22
Total with taxes and fees
Lakeview Golf Retreat 1BDR Condo 5057
A wooden boardwalk leading to a sandy beach with benches and a railing overlooking the sea.

17. The Shores Lake View Condo Unit 5681

The Shores Lake View Condo Unit 5681
2.5 star property
Williamsburg
9.6 out of 10, Exceptional, (8 reviews)
"Spend my Birthday there and I will definitely go back there, so clean and peaceful."
United States
Diamond
$397 nightly
The price is $421
Sep 21 - Sep 22
Total with taxes and fees
The Shores Lake View Condo Unit 5681
A stone-arched outdoor seating area with wicker furniture and a round table, overlooking a scenic view of the sea.

18. The Shores Lake Views Condo Unit 5577

The Shores Lake Views Condo Unit 5577
2.5 star property
Williamsburg
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful view and great location"
United States
Bonnie
$440 nightly
The price is $464
Sep 7 - Sep 8
Total with taxes and fees
The Shores Lake Views Condo Unit 5577
A spacious kitchen with wooden cabinets, a central island with stools, a stainless steel refrigerator, and a wooden staircase leading to an upper level.

19. Boardman Monarch Upscale River Lodge HOT Tub!

Boardman Monarch Upscale River Lodge HOT Tub!
2.0 star property
Traverse City
10.0 out of 10, Exceptional, (1 review)
"The view was amazing. Additionally the attentiveness of the team was amazing. I am looking to rebook soon!"
United States
Mary
$675 nightly
The price is $715
Sep 8 - Sep 9
Total with taxes and fees
Boardman Monarch Upscale River Lodge HOT Tub!
A bedroom with a bed, a dresser, a TV mounted on the wall, and a door leading to another room.

20. Front Street Retreat! Cozy Traverse City Condo

Front Street Retreat! Cozy Traverse City Condo
3.5 star property
Oak Park
$347 nightly
The price is $367
Oct 1 - Oct 2
Total with taxes and fees
Front Street Retreat! Cozy Traverse City Condo
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

Leelanau Sands Casino & Lodge

Leelanau Sands Casino & Lodge

10/10 Excellent
"Very nice place to stay. We got a room facing the bay - awesome."
Jeffrey 2-night trip
Posted less than an hour ago
Leelanau Sands Casino & Lodge

Find out more about Leelanau Peninsula Wineries

Everything you need to know about Leelanau Peninsula Wineries vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leelanau Peninsula Wineries vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

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Leelanau Peninsula Wineries vacation rentals: An excellent choice for every season

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Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $271 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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