Leelanau Peninsula Wineries Vacation Rentals from $360: Search Short-Term Rentals

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Our top choices for Leelanau Peninsula Wineries vacation rentals

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

1. The Birches

Lake Leelanau

$498 nightly

Sep 28 - Sep 29

Total with taxes and fees

A wooden deck with outdoor furniture and potted plants, surrounded by lush greenery.

2. Studio in Lake Leelanau with outside entrance, king bed, & WiFi

Lake Leelanau

Sherry W.

$285 nightly

Sep 24 - Sep 25

Total with taxes and fees

A two-story house with a balcony, a well-maintained lawn, and a large window.

3. Leelanau condo on golf course close to beaches, wineries, sand dunes, and more

Cedar

James Z.

$342 nightly

Sep 24 - Sep 25

Total with taxes and fees

A modern kitchen with dark wood cabinets, stainless steel appliances, and a large window providing natural light.

4. 🌲 The Birches ➠ Luxury Condotel in Downtown Lake Leelanau | U3

Lake Leelanau

Elizabeth L.

$459 nightly

Sep 27 - Sep 28

Total with taxes and fees

A log cabin with a porch, a deck, and a well-maintained garden.

5. Traverse City M-22 Cottage | Hot Tub, Beach Access

Traverse City

Janna J.

$502 nightly

Sep 24 - Sep 25

Total with taxes and fees

A lakeside view with a dock, chairs, and a picnic table.

6. One-bedroom cabin on Lake Leelanau. Sunset view. Dog considered.

Traverse City

Emily A.

$397 nightly

Sep 30 - Oct 1

Total with taxes and fees

A stainless steel kitchen counter with a charcuterie board, two glasses of champagne, and a stove in the background.

7. Come cozy up next to the fireplace at our contemporary condo centrally located

Cedar

Kathy M.

$388 nightly

Sep 28 - Sep 29

Total with taxes and fees

A bedroom with a large bed, two bedside lamps, a window with blinds, and a view of the outside.

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

Lake Leelanau

$646 nightly

Sep 27 - Sep 28

Total with taxes and fees

A beach with a grassy foreground and a calm sea.

9. OPEN for the Holidays! Near XC, Hiking & Wineries Easy Walk to Town!

Suttons Bay

Richard D.

$686 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

10. The Birches - Condotel in Lake Leelanau

Lake Leelanau

Jaspal

$477 nightly

Sep 24 - Sep 25

Total with taxes and fees

A two-story house with a covered porch and a small deck.

11. The Leland Blue on M-22

Suttons Bay

Krystina H.

$369 nightly

Oct 12 - Oct 13

Total with taxes and fees

A porch with two rocking chairs and a small table, a welcome sign, and a view of the surrounding landscape.

12. Cozy Countryside Farmhouse In Leelanau

Cedar

Alexa b.

$591 nightly

Sep 24 - Sep 25

Total with taxes and fees

A wooden cabin with a dining table set for four, large windows overlooking a lake, and a wooden deck.

13. Omena Point Paradise | Waterfront | Sunrise |

Omena

Erik S.

$481 nightly

Oct 7 - Oct 8

Total with taxes and fees

A room with a dining table and chairs, a view of the sea through large windows, and a ceiling fan.

14. Lake Michigan Waterfront Retreat - Traverse City, MI

Traverse City

James L.

$532 nightly

Sep 30 - Oct 1

Total with taxes and fees

A spacious living room with a view of the sea, a fireplace, and modern furniture.

15. LakeHaus Vibes + Hot Tub

Traverse City

Guy

$1,043 nightly

Sep 28 - Sep 29

Total with taxes and fees

A beach with a row of chairs facing the ocean, a clear sky, and a distant shoreline with trees.

16. Chalet By The Bay- a serene waterfront escape

Suttons Bay

Amy c.

A bed with patterned pillows, a gold lamp, and a view of a mountainous landscape through a window.

17. Waterfront Studio, newly renovated, A Cool Studio, Glen Arbor M22 Crystal River

Glen Arbor

Valerie F.

$446 nightly

Sep 28 - Sep 29

Total with taxes and fees

A rustic outdoor seating area with Adirondack chairs around a fire pit, a modern building in the background, and a string of lights above.

18. Leelanau Day Tripper - Modern Barndominium Retreat | Sauna • Bikes • Beaches • Wineries Sleeps 10 • 3 Bedrooms • 2.5 Bathrooms • Pet-Friendly

Cedar

Patrick M.

$729 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.

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

Suttons Bay

$915 nightly

Oct 8 - Oct 9

Total with taxes and fees

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

Suttons Bay

"Beautiful home with a perfect amount of space for 9 of us, very clean and very well-maintained. Perfect location between Traverse City and Suttons Bay, near countless wineries, cideries and restaurants. Loved having coffee in the morning on the front deck with a glimpse of the bay through the trees and birds singing, the kids (teens) enjoyed kayaking, and we all enjoyed time around the firepit in the evenings. Excellent home to reconnect with family and nature."

Melissa B.

$936 nightly

Oct 8 - Oct 9

Total with taxes and fees

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Top Leelanau Peninsula Wineries Hotel Reviews

Leelanau Sands Casino & Lodge

8/10 Good

"Registration was a problem as we were somehow double booked. But Stacy helped us and it was taken care of. We found used washcloths in our bathroom. Also had to request a hair dryer as we had none. The casino restaurant was just ok. No table service. Casino itself was ok. We didn’t spend much time there. No table games the day we were there."

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

10/10 Excellent

"Wonderful old school lake cottage with beautiful laid back beach. There are plenty of good spots to eat/ drink a short distance away and lots of outdoor activities. Aaron (owner) was on site but makes it a point to respect visitor's privacy, and he was very helpful and responsive with any questions or needs. We loved out time here."

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

8/10 Good

"The house was great, like stepping back into history. Location was fantastic. Beds were small and not very comfortable. The hot water heater was not very efficient. Could not take a bath and a shower at the same time without running out. FYI, the stairs to the loft are very steep, probably not great for really young children. If the beds and the hot water issues were resolved, I would give it five stars."

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 $360 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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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

2. Studio in Lake Leelanau with outside entrance, king bed, & WiFi

3. Leelanau condo on golf course close to beaches, wineries, sand dunes, and more

4. 🌲 The Birches ➠ Luxury Condotel in Downtown Lake Leelanau | U3

5. Traverse City M-22 Cottage | Hot Tub, Beach Access

6. One-bedroom cabin on Lake Leelanau. Sunset view. Dog considered.

7. Come cozy up next to the fireplace at our contemporary condo centrally located

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

9. OPEN for the Holidays! Near XC, Hiking & Wineries Easy Walk to Town!

10. The Birches - Condotel in Lake Leelanau

11. The Leland Blue on M-22

12. Cozy Countryside Farmhouse In Leelanau

13. Omena Point Paradise | Waterfront | Sunrise |

14. Lake Michigan Waterfront Retreat - Traverse City, MI

15. LakeHaus Vibes + Hot Tub

16. Chalet By The Bay- a serene waterfront escape

17. Waterfront Studio, newly renovated, A Cool Studio, Glen Arbor M22 Crystal River

18. Leelanau Day Tripper - Modern Barndominium Retreat | Sauna • Bikes • Beaches • Wineries Sleeps 10 • 3 Bedrooms • 2.5 Bathrooms • Pet-Friendly

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

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

Find vacation rentals that suit your style

Top Leelanau Peninsula Wineries Hotel Reviews

Leelanau Sands Casino & Lodge

Find out more about Leelanau Peninsula Wineries

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