The 29 Best Holiday Rentals in Lake Michigan Shore Wine Trail

Ranked 1 out of 241 in the region, as well as being 1 of 5 for holiday rentals in Douglas.

• “I didn’t know there was breakfast.”
• “Table and chairs outside the room.”
• “The accommodation was quaint, clean, and efficient.”
• See more reviews of Blue Star Motel

Ranked 2 out of 241 in the region, as well as being 2 of 13 for holiday rentals in Benton Harbor.

• “Great get away.”
• “Beautiful apartment!”
• “Clean and close to downtown Benton harbor”
• See more reviews of Benton Harbor Apt with Balcony and Fire Pit

Ranked 3 out of 241 in the region, as well as being 4 of 29 for holiday rentals in Saugatuck.

• “the cabin was really nice.”
• “A charming, comfortable, uber-clean cabin in a fantastic location”
• “Very cozy and maintained house.”
• See more reviews of Kingfisher Cove Cabin 2

Ranked 4 out of 241 in the region, as well as being 2 of 5 for holiday rentals in Douglas.

• “”
• “This was the perfect place for our stay in the Douglas / Saugatuk area.”
• “River view”
• See more reviews of Beacon Court D

Ranked 5 out of 241 in the region, as well as being 6 of 29 for holiday rentals in Saugatuck.

• “Other than initially finding the condo, the property was really, really nice.”
• “Great condo with nice balcony to enjoy”
• “Would visit Saugatuck again.”
• See more reviews of Lake View Getaway

Ranked 6 out of 241 in the region, as well as being 3 of 13 for holiday rentals in Benton Harbor.

• “Everything was clean and made us feel like we were home and...”
• “Good location, near stores, beach and downtown, the house...”
• “”
• See more reviews of Riverside Retreat

Ranked 7 out of 241 in the region, as well as being 11 of 23 for holiday rentals in South Haven.

• “Relaxing and comfortable and we loved it.”
• “Beautiful cabin!”
• “Cute, clean house with a few but's”
• See more reviews of La Maison Malabar - Gorgeous Luxury Cabin!

Ranked 8 out of 241 in the region, as well as being 4 of 15 for holiday rentals in New Buffalo.

• “Great location—quiet street and blocks from the beach.”
• “”
• “Excellent hosts! I needed an iron and there wasn’t one at the house, they got an iron to me within an hour!!! Excellent”
• See more reviews of Eagles Beach Nest II

Ranked 9 out of 241 in the region, as well as being 5 of 15 for holiday rentals in New Buffalo.

• “”
• “Girls getaway”
• “”
• See more reviews of Walking Distance To Beach And Shops

Ranked 10 out of 241 in the region, as well as being 7 of 29 for holiday rentals in Saugatuck.

• “”
• “Lovely place to make memories, making good use of the front porch and seeing surrounding area.”
• “Great location close to downtown, Great size and very...”
• See more reviews of Kingfisher Cove Cabin 19

Ranked 11 out of 241 in the region, as well as being 8 of 29 for holiday rentals in Saugatuck.

• “Excellent/relaxing”
• “Bob the manager was nice, thats about it- see above-not happy”
• “couches /beds in living room were NOT comfortable, bed...”
• See more reviews of Arrowhead Resort

Ranked 12 out of 241 in the region, as well as being 1 of 3 for holiday rentals in Fennville.

• “A beautiful and peaceful cottage retreat nestled in nature!”
• “A beautiful and peaceful getaway with everything you could need.”
• “Everything was perfect! Amazing get away with beautiful local beaches.”
• See more reviews of Blue Vieira Cottage

Ranked 13 out of 241 in the region, as well as being 11 of 29 for holiday rentals in Saugatuck.

• “Had a fun girls weekend away celebrating a birthday. Great rental for what we wanted.”
• “All 8 of us very much enjoyed our stay and would definitely recommend it to others.”
• “Would love to bring the family.”
• See more reviews of Borrowed Thyme

Ranked 14 out of 241 in the region, as well as being 12 of 29 for holiday rentals in Saugatuck.

• “Excellent location”
• “The unit was OK, but I would hesitate to recommend it to a friend.”
• “Amazing location right in the downtown area”
• See more reviews of Walk to Water St and River Quaint Saugatuck Apt

Ranked 15 out of 241 in the region, as well as being 13 of 29 for holiday rentals in Saugatuck.

• “Lovely, spacious cottage very close to downtown. Clean, not cluttered with a delicious screened-in porch to squander tim”
• “Enjoyed stay. Would definitely come back”
• “Great location, clean house!”
• See more reviews of The Swallow

Ranked 16 out of 241 in the region, as well as being 14 of 29 for holiday rentals in Saugatuck.

• “Location”
• “Cute little cozy weekend getaway”
• “My husband and I enjoyed stay.”
• See more reviews of Hummingbird

Ranked 17 out of 241 in the region, as well as being 3 of 4 for holiday rentals in Paw Paw.

• “So enjoyed our stay & the weather in December was actually mild enough that I was able to kayak around the lake one”
• “Quaint and laid-back stay with convenience to fish bite on property”
• “Amazing property!”
• See more reviews of Cozy Quonset Hut On Maple Lake

Ranked 18 out of 241 in the region, as well as being 3 of 5 for holiday rentals in Douglas.

• “”
• “Get Out!”
• “Location great convenience”
• See more reviews of Bluebird Condo

Ranked 19 out of 241 in the region, as well as being 16 of 29 for holiday rentals in Saugatuck.

• “My friend and I found the cottage very comfortable, nicely equipped with just about anything we might need if we wished”
• “A great walkable place with a nice hot tub!”
• “Girls getaway”
• See more reviews of Nightingale

Ranked 20 out of 241 in the region, as well as being 18 of 28 for holiday rentals in Holland.

• “Excellent. Will definitely be staying here again!”
• “I had a great time staying here, appreciated my helpful host and proximity to all Saugatuck has to offer!”
• “The cozy Holland studio was cozy, updated, and relaxing.”
• See more reviews of Studio by Lake Michigan Homestead Experience!

Ranked 21 out of 241 in the region, as well as being 18 of 29 for holiday rentals in Saugatuck.

• “”
• “Beautiful apt centrally located”
• “Stress free!”
• See more reviews of Charming Saugatuck Condo with Private Deck and Grill!

Ranked 22 out of 241 in the region, as well as being 3 of 3 for holiday rentals in Fennville.

• “Great for a small family weekend”
• “Charming Property”
• “Not an appropriate rental for two older adult couples.”
• See more reviews of The charming Glenn Cottage! Walk to Lake Michigan!

Ranked 23 out of 241 in the region, as well as being 4 of 5 for holiday rentals in Douglas.

• “Lovely house, great location, peaceful neighborhood. Pure Michigan!”
• “Easy check in , easy check out , owner responds quickly , clean , walking distance to town , comfy bed!”
• “Relaxing, comfortable, feels like home”
• See more reviews of Douglas Hideaway

Ranked 24 out of 241 in the region, as well as being 19 of 29 for holiday rentals in Saugatuck.

• “Wonderful views”
• “Would come back to enjoy again”
• “Location was perfect!”
• See more reviews of Riverside Suites - Unit B

Ranked 25 out of 241 in the region, as well as being 20 of 29 for holiday rentals in Saugatuck.

• “Stay in the heart of Saugatuck”
• “Fabulous apartment on the river with amazing views, close to everything Saugatuck has to offer!”
• “We were there a total of about 4 hours”
• See more reviews of Riverside Suites - Unit A

Ranked 26 out of 241 in the region, as well as being 8 of 15 for holiday rentals in New Buffalo.

• “Had a good stay, cute house”
• “Stay away”
• “Scenic morning pool view with a brilliant beach sunset.”
• See more reviews of Anchors Away

Ranked 28 out of 241 in the region, as well as being 10 of 15 for holiday rentals in New Buffalo.

• “It was a slice of heaven, and we’d love to come back one day.”
• “Very good value and location for small families and accommodating for pets.”
• “Would stay again! Loved the garage and location.”
• See more reviews of Square Toe's Last Resort

Ranked 29 out of 241 in the region, as well as being 4 of 4 for holiday rentals in Portage.

• “I would go there again”
• “Cute house and decor.”
• “Enjoyed our stay, it was perfect for this trip! Would definitely stay here again!”
• See more reviews of Amazing Lakefront Retreat On Long Lake! home

Ranked 30 out of 241 in the region, as well as being 21 of 29 for holiday rentals in Saugatuck.

• “Location!”
• “Great location”
• “We loved the cottage and so did our English Bulldog. Location is close to everything. Loved watching the boats go bye.”
• See more reviews of Anna's Cottage