Find Hotels with an Outdoor Pool in Southwest Michigan, MI

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Check availability on Southwest Michigan Hotels with an Outdoor Pool

Our top choices for Southwest Michigan hotels with an outdoor pool

Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo
3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1639)
"Great place, hotel room is very well appointed. "
United States
Stuart
$109 nightly
The price is $115
Dec 15 - Dec 16
Total with taxes and fees
Four Winds Casino Resort – New Buffalo

The Inn At Harbor Shores

The Inn At Harbor Shores
3.5 star property
Saint Joseph
9.0 out of 10, Wonderful, (1005)
"Everything was great!"
United States
Kristen
$164 nightly
The price is $181
Dec 24 - Dec 25
Total with taxes and fees
The Inn At Harbor Shores

Cassopolis Cabin, Little Fish Lake On-site!

Cassopolis Cabin, Little Fish Lake On-site!
3.0 star property
Cassopolis
$236 nightly
The price is $250
Dec 14 - Dec 15
Total with taxes and fees
Cassopolis Cabin, Little Fish Lake On-site!

Best Western Benton Harbor-St. Joseph

Best Western Benton Harbor-St. Joseph
2.5 star property
Benton Harbor
7.8 out of 10, Good, (1000)
"Very nice staff, very quiet and clean"
United States
Sarah
$67 nightly
The price is $75
Dec 18 - Dec 19
Total with taxes and fees
Best Western Benton Harbor-St. Joseph

Goldberry Woods

Goldberry Woods
3.5 star property
Union Pier
9.8 out of 10, Exceptional, (42)
"Beautiful, quiet property. A peaceful night at a fantastic property in the woods. "
United States
Donald
$224 nightly
The price is $238
Dec 29 - Dec 30
Total with taxes and fees
Goldberry Woods

Holiday Ready Winter Retreat-Close to Swiss Valley Ski & Trails

Holiday Ready Winter Retreat-Close to Swiss Valley Ski & Trails
Dowagiac
10.0 out of 10, Exceptional, (3)
"house was clean and a awesome place to stay family is wanting to come back this summer and reserve it again thank you !!!!!!"
United States
james j.
$370 nightly
The price is $370
Dec 18 - Dec 19
Total with taxes and fees
Holiday Ready Winter Retreat-Close to Swiss Valley Ski & Trails

Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets

Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets
Union Pier
8.0 out of 10, Very Good, (8)
"We enjoyed our stay. It’s a fun property being an old school building and they’ve added lots of for the kids and adults. "
United States
Tim D.
$832 nightly
The price is $843
Dec 14 - Dec 15
Total with taxes and fees
Schoolhouse now 5K Sq ft Lux BNB: Gym, Sauna, HotTub, GameRoom, Billiards, pets

Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach
New Buffalo
9.8 out of 10, Exceptional, (34)
"Pool and jet tub excellent. Great getaway with family . Cottage clean and well maintained and quick response from host . "
United States
Hanneli J.
$476 nightly
The price is $501
Dec 15 - Dec 16
Total with taxes and fees
Creekside House on 30 Acres with Kayaks/Pool/Farm/River/Trails/Pets, near Beach

Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!

Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!
2.0 star property
Union Pier
10.0 out of 10, Exceptional, (1)
"Had an amazing time, gorgeous set up, beautiful surroundings and fresh farm produce all weekend long"
United States
guy g.
$510 nightly
The price is $537
Dec 15 - Dec 16
Total with taxes and fees
Deerpath Cottage-30 Acres with Indoor Pool, Farm, Kayaking, Trails, by Beach!

Modern Farmhouse steps from downtown New Buffalo & Lake Michigan!

Modern Farmhouse steps from downtown New Buffalo & Lake Michigan!
Downtown New Buffalo
10.0 out of 10, Exceptional, (181)
"Our third stay at this property. It just gets better every year! "
United States
Richard H.
$1,000 nightly
The price is $1,053
Dec 31 - Jan 1, 2026
Total with taxes and fees
Modern Farmhouse steps from downtown New Buffalo & Lake Michigan!
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.

Find out more about Southwest Michigan

Discover top Southwest Michigan attractions

Southwest Michigan is a paradise for travelers seeking relaxation and family-friendly activities. Start your journey at the stunning Silver Beach County Park in St. Joseph, where children can splash in the calm waters of Lake Michigan while adults unwind on the soft sand or enjoy a picnic with scenic views of the iconic lighthouse. Just a short drive away, the charming town of Saugatuck invites you to explore its art galleries and indulge in a leisurely boat cruise along the Kalamazoo River, surrounded by lush landscapes. For a touch of adventure, head to the dunes at Warren Dunes State Park, where families can hike or simply lounge on the beach, followed by a sunset that paints the sky in captivating hues. If you're in the mood for a taste of local flavors, the wineries of the Lake Michigan Shore Wine Trail offer delightful tours and tastings that you can savor together. Stay in the picturesque town of South Haven, where hotels featuring refreshing pools provide a perfect retreat after a day of exploration—imagine relaxing by the water, sipping a cocktail while the kids splash nearby. The cozy, family-friendly accommodations here ensure attentive service, making your stay as restful as it is enjoyable.

Top Southwest Michigan Hotel Reviews

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