Holiday rentals with a pool in Berrien County

A-Frame On Lake Michigan - beach, sports, + pool

The Chalets on the Lake is a unique community, right on Lake Michigan with all the amenities for a perfect Michigan Summer: heated swimming pools (Memorial-Labor Day), a kiddie pool, tennis courts, basketball courts, pickleball, a private beach and more! This chalet has a view of the lake, perfect for sunsets and walks to the beach. A private home with a queen bed, full bed, 2 sets of bunk beds, bathroom, fully equipped kitchen, Roku TV’s, high speed internet, AND a miniature foosball table.

Updated Pool House with Private Pickle Ball Court

Ideal for families this is the perfect escape from city life. Our repurposed barn is a unique "Glamping" adventure, wake up to the crow of our roosters and enjoy fresh eggs every day. Just outside of St Joe & Benton Harbor, enjoy your stay in this repurposed old hatchery with exclusive use of the in-ground pool. Take advantage of the 30 acres surrounded by a creek & river or make us your home base for exploring the wineries, golf courses, hiking trails & beaches in the surrounding area.

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.

Lake Michigan Beach Cottage + Pool + Games

Escape to our newly remodeled chalet that is steps away from Lake Michigan. With 6 beds, it's the perfect getaway for couples, families, or small groups. Enjoy access to a private and public beach, pools, sports courts, fishing ponds, and playgrounds. Located next to Lincoln Township Park and near Grand Mere State Park plus nearby breweries, wineries, and distilleries. Relax, explore, and create unforgettable memories at this cozy lakeside retreat. Your perfect vacations awaits!

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.

Marina's Edge

Stay in the heart of downtown New Buffalo at Marina’s Edge, a three-story townhouse directly across from the marina and just steps from Stray Dog, shops, dining, and Lake Michigan. Enjoy open-concept living, three comfortable bedrooms, multiple full baths, garage parking, and front porch and balcony views of the harbor. Guests also have access to a heated association pool in summer. Walk everywhere, soak up the energy, and experience Harbor Country at its most vibrant.

Harbert Home With Private Pool and Hot Tub

Pool Open April 10-Nov 2nd. Hot Tub Open Year-round! Located in the charming community of Harbert we welcome you to Sunset Shores Cottage! This amazing home has EVERYTHING you could ask for in a vacation rental. Just steps away (100 yards or less) from the largest beach in Harbor Country as well as having your own private heated pool and two hot tubs! Stand-alone hot tub open year-round! Lake views from many parts of the house as well. Outdoor firepit and grill.

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) .

24 Acre Luxury Villa| Heated Pool & Hot Tub|Pond

Escape to Bramblewood! 24-acre Private Villa off the Coast of Lake Michigan! This STUNNING, Brand New, Custom Built Home offers 4-bedroom, 3.5-bathroom to comfortably accommodate 10 guests. Relax and Unwind in the heated swimming pool or jacuzzi hot tub. This IDEAL location is just 15 minutes from the Coastal Towns of St. Joseph and South Haven!

License To Chill in Sun Coast Park

We are located in Sawyer MI. Directly across the street from Warren Dunes State Park. You can walk, bike, or drive to beach. It's a 3/4 mile walk to beach. If you walk or bike into park, there's no charge for entrance fee. We have a commercial in ground pool, heated. It's available for your use during daylight hours. License To Chill is unit #14.