Leelanau Peninsula Wineries Vacation Rentals from $342: Search Short-Term Rentals

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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

Lake Leelanau

Jaspal

$477 nightly

Sep 20 - Sep 21

Total with taxes and fees

A modern kitchen with dark cabinetry, stainless steel appliances, a large window, and two bar stools.

2. The Birches

Lake Leelanau

$511 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

Lake Leelanau

$599 nightly

Oct 18 - Oct 19

Total with taxes and fees

A deck with Adirondack chairs, a round table, and a glass railing overlooking a forested area.

4. Wineries, Kayaking, Hot Tub, Fire Pit on the Lake

Suttons Bay

$933 nightly

Oct 8 - Oct 9

Total with taxes and fees

A modern living room with a sofa, a coffee table, and a TV on a wooden stand.

5. Boardwalk Suites & Residences By Kasa

Downtown Traverse City

Lauren

$82 nightly

Sep 20 - Sep 21

Total with taxes and fees

6. Pinestead Reef Resort

Traverse City

Sherry

$159 nightly

Sep 21 - Sep 22

Total with taxes and fees

7. 539 Bay Street Traverse City - Luxury Downtown Residences

Slabtown

Chris

$360 nightly

Sep 28 - Sep 29

Total with taxes and fees

A spacious living room with a sofa, coffee table, and chairs. There are large windows with curtains, a patterned rug, and artwork on the walls.

8. Front Street Retreat! Cozy Traverse City Condo

Oak Park

$347 nightly

Oct 1 - Oct 2

Total with taxes and fees

A bedroom with a large bed, a nightstand, a chair, and a window.

9. Mahaney Suite BW Boutique Hotel

Central Lake

Jon

$122 nightly

Oct 14 - Oct 15

Total with taxes and fees

A round table with four black wire mesh chairs, surrounded by grass and trees, with a house in the background.

10. The Flat by Wanderlust Abodes

Central Lake

Waclaw

$162 nightly

Oct 8 - Oct 9

Total with taxes and fees

A modern living room with a leather sofa, a round coffee table, and a large window offering a view of trees and a building.

11. The Kroger Lofts

Charlevoix

Robert

$606 nightly

Sep 21 - Sep 22

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

12. The Loop Downtown By Kasa

Downtown Traverse City

Roy

$134 nightly

Oct 18 - Oct 19

Total with taxes and fees

A wooden boardwalk leading to a sandy beach with benches and a railing overlooking the sea.

13. The Shores Lake View Condo Unit 5681

Williamsburg

Diamond

$244 nightly

Sep 20 - Sep 21

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, a glass-top table with bar stools, and wooden flooring.

14. Traverse City Condo: Half Mi to Front Street!

Downtown Traverse City

Joseph

$248 nightly

Sep 22 - Sep 23

Total with taxes and fees

A bedroom with a large bed, a ceiling fan, wooden flooring, and large windows.

15. Amelia Room BW Boutique Hotel

Central Lake

Karen

$109 nightly

Oct 15 - Oct 16

Total with taxes and fees

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

Williamsburg

Erica

$295 nightly

Sep 21 - Sep 22

Total with taxes and fees

A modern kitchen with a stainless steel refrigerator, a round dining table with bar stools, and a decorative vase with flowers.

17. 3 Mi to Lake Michigan: The Country Cottage

Central Lake

Kristin

$267 nightly

Sep 23 - Sep 24

Total with taxes and fees

A bedroom with a large bed, a ceiling fan, a window with curtains, and a radiator.

18. Charlie Room BW Boutique Hotel

Central Lake

Tonya

$116 nightly

Oct 7 - Oct 8

Total with taxes and fees

19. The Shores Lakeside Condo Unit 5680

Williamsburg

Jennifer

$271 nightly

Sep 20 - Sep 21

Total with taxes and fees

A modern living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

20. Walk to Front St! Traverse City Condo Near Skiing

Oak Park

"We stayed in this unit June 23-25 (2 nights). Overall we were happy with the unit and the area. The only problem we discovered came a few days after we left. One of our party of 4 discovered several small bites on her legs that got progressively worse over a couple of days, leading her to go to urgent care. The doctor diagnosed them as bed bug bites. She was in the bedroom with the queen bed. The sheets on the bed were dark gray so any evidence of bed bugs would have been difficult to see,...

David

$353 nightly

Oct 1 - Oct 2

Total with taxes and fees

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Top Leelanau Peninsula Wineries Hotel Reviews

Charming & renovated airy Train Depot turned cottage steps from Lake Michigan

10/10 Excellent

"Cynthia knows how to make guests feel welcome. She is a great communicator and very accommodating. We wanted to make sure bikes and a grill were available. She not only provided 3 bikes (instead of the 2 in the listing), she provided a brand new gas grill with all the needed tools and an extra LP tank! The house is a show place and immaculately clean. Everything works as it should including a full sized washer and dryer. The kitchen makes eating in a pleasure. There are interesting touches throughout the house and the furniture and beds are very comfortable. It would be impossible not to enjoy a stay at the Wildflower Depot."

Leland Lodge

8/10 Good

"The Leland Lodge is a step back to a quieter time. Beautiful grounds abutting a private golf course Make for quiet nights and peaceful views. The property is impeccably maintained-very clean. The staff was friendly and very helpful. Leland is a picturesque town with good restaurants and access to loads of outdoor activities. There is a sandy beach on Lake Lelanau just a short walk from the lodge. I would definitely return for a longer stay in the future. My only complaint is I was surprised to find there was not an elevator as most rooms were on the second floor-unfortunate for this day and age."

Quiet and private sandy bottom lakefront

8/10 Good

"We had a great time. The place was super clean and nice with a great little dock and indoor and outdoor porch. The place is close to the other houses with the owners living right next door. They were super nice and helpful, and we enjoyed talking to them. If you are looking for a place on the lake that is very private this may not be the place. The only things that I feel could be better, but they are super minor is a designated parking spot for the rental house that is well designated. Blinds that can close on the window facing the lake. All other windows have blinds but these and the way other houses are placed they can see in the house from theirs and last is a sidewalk or paving stones leading to the front door, so you don't have to walk through the grass if you use that door. There is a sidewalk going to the back door, but it takes you next to the homeowner's place which makes you feel like you are invading their home. Again, we really loved the place and had a fantastic time. No place is perfect so my little minor things definitely would not keep us from staying their again."

PineBay Hideaway! Two bedroom, 1 bath, private area. Sleeps 5 plus pullout sofa.

10/10 Excellent

"We had a wonderful stay. The room was very comfortable and a great place to relax. There were plenty of things for the kids to play with and amenities to enjoy. Overall, a great trip. We’d stay again."

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.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leelanau Peninsula Wineries vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

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

Whenever you want to travel, a warm welcome awaits you in Leelanau Peninsula Wineries. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Leelanau Peninsula Wineries in high season.

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 $342 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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At Expedia, we put the best Leelanau Peninsula Wineries vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Leelanau Peninsula Wineries rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leelanau Peninsula Wineries vacation.

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Check prices for these dates

Our top choices for Leelanau Peninsula Wineries vacation rentals

1. The Birches - Condotel in Lake Leelanau

2. The Birches

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

4. Wineries, Kayaking, Hot Tub, Fire Pit on the Lake

5. Boardwalk Suites & Residences By Kasa

6. Pinestead Reef Resort

7. 539 Bay Street Traverse City - Luxury Downtown Residences

8. Front Street Retreat! Cozy Traverse City Condo

9. Mahaney Suite BW Boutique Hotel

10. The Flat by Wanderlust Abodes

11. The Kroger Lofts

12. The Loop Downtown By Kasa

13. The Shores Lake View Condo Unit 5681

14. Traverse City Condo: Half Mi to Front Street!

15. Amelia Room BW Boutique Hotel

16. Lakeview Golf Retreat 1BDR Condo 5057

17. 3 Mi to Lake Michigan: The Country Cottage

18. Charlie Room BW Boutique Hotel

19. The Shores Lakeside Condo Unit 5680

20. Walk to Front St! Traverse City Condo Near Skiing

Find vacation rentals that suit your style

Top Leelanau Peninsula Wineries Hotel Reviews

Charming & renovated airy Train Depot turned cottage steps from Lake Michigan

Find out more about Leelanau Peninsula Wineries

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