Holiday rentals with a pool in Berrien County

101 is all the fun! Arcade + Pool + Beach

If this is your first time to the Chalet at the Lakes, it won’t be your last. This unique beach front gated community has it all! Chalet 101 - 2 bdrms and is located across from the pond. Not beachfront. The community includes heated pool, tennis courts, pickleball courts, private beach, 3 playgrounds, shuffleboard, basketball courts, sand volleyball, 2 community fire pits, and direct access to Lincoln Park Beach. And for adult vacays, you are just minutes from breweries and wineries galore!

| Fire Pit | Hot Tub | Dog Friendly

Welcome to your idyllic farmhouse retreat located in Southwest Michigan. This 4-bedroom, 2.5 bathroom farmhouse is a unique blend of rustic charm and modern comfort, making your stay exceptional. Your kids will love the pool (closed post Labor Day) & HOT TUB, you will love sipping your coffee from the porch while watching them, and your dogs will love being with you on vacation. You have access to Internet with Starlink or you could tell the kids there isn’t any internet and step back in time.

Modern Farmhouse w/ Pool Near St Joe

Your private oasis awaits you! Forget your worries in this spacious and serene space. This classic farmhouse has 3 bedrooms & 2 full baths. There is a large in ground heated pool that is open May to thru Sept. We are located in Berrien County that is well know for the many wine tour offerings. We are only 15 mins from St. Joseph, MI that offers beautiful sandy beaches, quaint shops, festivals, farmers markets, wineries & more! We have a full kitchen, washer/dryer & fast internet.

Amazing Beach Condo with pool and great sunsets!

Unwind with your family at this peaceful getaway! This cozy retreat features 1 bedroom, 1.5 bathrooms, and a pull-out couch in the living room. Enjoy exclusive access to a private beach and a community pool reserved for the condo association. Relax on your private deck while taking in breathtaking sunsets, just a short 5-minute walk from the beach! Located between South Haven and St. Joseph, Michigan, this charming spot offers easy access to local wineries, nature centers, parks, and more!

Buchanan Pool House 2 King Beds 25 min to ND

Welcome to Buchanan Pool House! The home was built in 1897 and is nestled in a beautiful area of many historic homes. After floating/playing all day in the pool, enjoy sitting out on the front porch swing or rocking chairs with a tall, cool drink. Fun times can be had in the game room with the family. Many board games are available, plus a poker table with chips and cards. Time for some Texas Hold 'em! Each bedroom has darkening shades or curtains to ensure a peaceful sleep. Enjoy!

Play @ The Hideaway - hot tub, sauna, gymnasium

Accommodating up to 22 guests, this expansive 5,891 sqft property is set on 22.6 acres, creating a private oasis complete with a pool, hot tub, sauna, and gymnasium. The residence features a Great Room, fireplace, fire pit, and a private trail, making it an ideal setting for relaxation and recreation. With 3 king-size beds, 4 queen-size beds, and 2 bunk beds with trundles, comfortably catering to the needs of large groups. This venue offers enjoyable experiences for guests of all ages.

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

Bibi's Retreat- Grand 7 Bedroom Private Escape

Bibi's Retreat-Nestled among 6,000 trees along 15 acres of secluded property. This is the ultimate private getaway. Located in Niles, MI, the home offers 7 true bedrooms with plenty of space for multi-family living. We are within 30 min of 15 wineries and breweries. We are within 20 min of 10+ golf courses and 20 min to Notre Dame. Ladies Retreat, Golf Getaway or Winery Tours, this home is perfect for large groups.

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool and hot tub. Property on 6 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 2 new homes on 6 acre property, this home and 1 guest home ( rented separately) .

Dunescape Beach Retreat, Downtown New Buffalo

Luxury & Location. A spacious beach getaway in the heart of down town New Buffalo and a short walk from the Marina and the beach. Start the day with the view from the rooftop deck before hitting the private Dunescape pool! Just over an hour from Chicago whether by car or train - the train station is just steps from Beach Retreat.

After Dune Delight in Sun Coast Park

We are located in a small Tiny Home park. Full kitchen, sleep up to 6. Directly across street from Warren Dunes State Park. Wineries, breweries all within easy driving distance. Beach Bucket Ice cream shop next door. Walk and bike back to dunes for free. Come and relax with us! After Dune Delight is unit #18.