Holiday Homes in Southwest Michigan

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Southwest Michigan

Beautiful woodsy setting a 10 minute walk to the beach!
Stroll down the staircase to the serene beach, flanked by trees and a clear path.

Beautiful woodsy setting a 10 minute walk to the beach!

9.0 out of 10, Wonderful, (16)
"Very smooth, exactly as described!"
Beautiful woodsy setting a 10 minute walk to the beach!
Breezy Pad, Close to the Lake, with Hot Tub
Relax in this inviting living room with a flat-screen TV, comfortable sofa, and dining area.

Breezy Pad, Close to the Lake, with Hot Tub

9.2 out of 10, Wonderful, (89)
"We had a great time and appreciated the little touches that made our stay great! "
The price is AU$469
includes taxes & fees
14 Aug - 15 Aug
Breezy Pad, Close to the Lake, with Hot Tub
Cozy Cottage: Summer Getaway & Evenings by the Fire
Enjoy cooking in this well-lit kitchen with a central island and modern appliances.

Cozy Cottage: Summer Getaway & Evenings by the Fire

9.2 out of 10, Wonderful, (5)
"Quiet, well stocked with basics for cooking, relaxation. We had some trouble getting streaming to stay engaged to internet, but only meant that we watched less TV, which worked for us. We would rent with you and this place specifically again."
Cozy Cottage: Summer Getaway & Evenings by the Fire
Relax Lakefront-Stunning Lake Views in Popular Sister Lakes! Private Sand Beach!
Enjoy a peaceful retreat with a view of the serene lake and forested shoreline from this cozy space.

Relax Lakefront-Stunning Lake Views in Popular Sister Lakes! Private Sand Beach!

10.0 out of 10, Exceptional, (59)
"This house accommodated our large crew. The host was very responsive, and we look forward to staying in the future."
Relax Lakefront-Stunning Lake Views in Popular Sister Lakes! Private Sand Beach!
Driftwood Cottage, a charming 3-bed/2-bath home in peaceful Union Pier!
Relax in a charming room with a wooden ceiling, large windows, and a view of lush greenery.

Driftwood Cottage, a charming 3-bed/2-bath home in peaceful Union Pier!

9.0 out of 10, Wonderful, (4)
"Great spot for a weekend getaway. Close to a great beach, shops, restaurants and a weekend farmers market. Check in was easy and the kitchen had all the supplies we needed. "
Driftwood Cottage, a charming 3-bed/2-bath home in peaceful Union Pier!
Perfect Location for your Beach/Lake MI stay! You'll Love This Beautiful Home!
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and toaster.

Perfect Location for your Beach/Lake MI stay! You'll Love This Beautiful Home!

10.0 out of 10, Exceptional, (47)
"The house was very clean and in a grrat location "
Perfect Location for your Beach/Lake MI stay! You'll Love This Beautiful Home!
'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!
Set amidst a serene suburban neighborhood, this single-story house offers a porch and a spacious deck.

'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!

10.0 out of 10, Exceptional, (192)
"Awesome property for a single family..great layout..perfect location "
'Rustic Refined Retreat’ Lakeside Home - Walk to Everything!
Three Oaks, Michigan. Beautiful Southwestern Michigan
Enjoy a serene beach experience with access to the ocean.

Three Oaks, Michigan. Beautiful Southwestern Michigan

9.8 out of 10, Exceptional, (17)
"This was a perfect place to stay near New Buffalo but away from the craziness. Cute house and nicely updated. Super comfy and had everything we needed. Highly recommend!"
Three Oaks, Michigan. Beautiful Southwestern Michigan
Welcome to Holiday House! Cozy, modern home 7 min. from the beach and wineries.
Relax in a serene outdoor space with a cushioned bench and wicker chairs.

Welcome to Holiday House! Cozy, modern home 7 min. from the beach and wineries.

10.0 out of 10, Exceptional, (43)
"The house was very clean and comfortable! We had a wonderful time!"
Welcome to Holiday House! Cozy, modern home 7 min. from the beach and wineries.
Beautiful all-new 5br/5.5ba home with private beach and hot tub in Union Pier!
Enjoy cooking in this kitchen with a stainless steel range, microwave, and dark cabinets.

Beautiful all-new 5br/5.5ba home with private beach and hot tub in Union Pier!

10.0 out of 10, Exceptional, (2)
"Great house and location - 1 block from the beach. New house with plenty of space to relax and everything you need for a fun weekend. Look forward to staying here next summer! "
Beautiful all-new 5br/5.5ba home with private beach and hot tub in Union Pier!
In the Heart of Three Oaks - Steps to Downtown
Enjoy cooking in this well-lit kitchen with large windows offering views of the surrounding area.

In the Heart of Three Oaks - Steps to Downtown

10.0 out of 10, Exceptional, (98)
"Great Place, we would stay again"
In the Heart of Three Oaks - Steps to Downtown
John's Beachside Cottage -- Short Walk To Terrific Lake Michigan Beach
Enjoy a serene beach experience with access to the ocean.

John's Beachside Cottage -- Short Walk To Terrific Lake Michigan Beach

9.4 out of 10, Exceptional, (60)
"This property was exactly what I needed for my situation. It was perfectly located, clean, included everything I needed to have a comfortable stay, and the host was great to work with."
John's Beachside Cottage -- Short Walk To Terrific Lake Michigan Beach
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
Relax on the covered porch with wicker furniture and lush greenery.

Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

10.0 out of 10, Exceptional, (168)
"This property is beautiful with a lot of space, bedrooms, and bathrooms. The location was perfect for walking to the beach, restaurants, and shopping. Can't wait to visit again!"
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!
Cozy Cottage close to the Lake
Relax in a serene natural setting surrounded by trees and a well-maintained lawn.

Cozy Cottage close to the Lake

9.6 out of 10, Exceptional, (48)
"This is a great spot for visiting Warren Dunes State Park and beach, Journeyman Distillery and various wineries. "
Cozy Cottage close to the Lake
Charming & cozy in-town retreat in the heart of New Buffalo
Enjoy cooking in this well-equipped kitchen with a central island and ample storage.

Charming & cozy in-town retreat in the heart of New Buffalo

10.0 out of 10, Exceptional, (159)
"Fantastic stay! We celebrated two milestones - our 18th wedding anniversary, as well as our first vacation as a family of three (8 month old daughter). We can’t say enough wonderful things about the house, location, and excellent communication with the property owners! They thought of everything with all the labeled items and beautiful decor to make your stay comfortable. Walkable and close to restaurants, shopping, and more. Thank you for the special memories! "
Charming & cozy in-town retreat in the heart of New Buffalo
Quiet neighborhood home Hot tub Fire pit Large deck Bar blocks to brewery
Dining

Quiet neighborhood home Hot tub Fire pit Large deck Bar blocks to brewery

9.8 out of 10, Exceptional, (100)
"Loved the property and space inside the house. Will definitely return."
Quiet neighborhood home Hot tub Fire pit Large deck Bar blocks to brewery
Napier House-Romantic Private Luxury mins to Beach
Relax in a warm and inviting space with a comfortable sofa and a touch of greenery.

Napier House-Romantic Private Luxury mins to Beach

9.0 out of 10, Wonderful, (9)
"Well appointed home and charming. "
The price is AU$611
includes taxes & fees
2 Sept - 3 Sept
Napier House-Romantic Private Luxury mins to Beach
Cozy Quiet at Mill Pond Cottage
Relax on the deck overlooking a serene water view surrounded by lush greenery, complete with a pool and outdoor seating area.

Cozy Quiet at Mill Pond Cottage

8.0 out of 10, Very good, (8)
"The host was very fast to respond to any messages, beds were super comfortable & it wasn't to far out of town! "
The price is AU$498
includes taxes & fees
3 Sept - 4 Sept
Cozy Quiet at Mill Pond Cottage
Charming home with sunroom, large yard, full kitchen, & washer/dryer
Fridge, microwave, oven, stovetop

Charming home with sunroom, large yard, full kitchen, & washer/dryer

8.8 out of 10, Excellent, (6)
"Great location close to all the places I wanted to go. Nice, clean property that provided everything I needed. I’d definitely stay here again."
Charming home with sunroom, large yard, full kitchen, & washer/dryer
Fisher's Fancy l Near the river & in house games!
Relax in this serene living space with a sofa, coffee table, and area rug, offering a peaceful view of the surrounding landscape from the balcony.

Fisher's Fancy l Near the river & in house games!

9.6 out of 10, Exceptional, (38)
"Close to town and the schools. "
Fisher's Fancy l Near the river & in house games!
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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