Holiday rentals with a pool in Berrien County

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Top-rated rentals with a pool in Berrien County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

A large screened front porch is furnished with several wooden rocking chairs and a wicker seating area. Natural light filters through the screens, showcasing the surrounding greenery. A small table sits centrally, creating an inviting space for relaxation and conversation.

Cabin in Three Oaks

4.86 out of 5 average rating, 112 reviews

Cabin with POOL in family resort!

Nestled within a gated 67-acre resort and just minutes from the shores of Lake Michigan, this charming cabin offers a peaceful retreat ideal for couples, families, or solo travelers, blending rustic décor with modern comforts. Guests can spend their days exploring nearby nature trails, lounging by the pool, paddling across the lake, or unwinding on the porch. The perfect vacation for exploring nearby orchards and countryside, catching live music or theater, or just slowing down and recharging!

Guest favourite

Home in Union Pier

5 out of 5 average rating, 14 reviews

Harbor Country Poolside

Harbor Country Poolside is a private luxury retreat in Union Pier, just minutes from Lake Michigan’s beaches. This 3-bedroom, 2.5-bath cottage features designer furnishings, plush bedding, and a fully equipped entertainer’s kitchen. Outdoors, enjoy resort-style amenities including a private, heated, saltwater pool, spa hot tub, fire pit, and serene three-season room surrounded by lush trees. Every space has been thoughtfully curated for relaxation and connection. 2026 Pool Dates: 5/7 - 10/11.

Top guest favourite

The exterior of the cottage features vibrant blue siding and a covered porch with white railings. Lush greenery and landscaped beds surround the entrance, creating a serene and welcoming façade. A pathway leads to the front door, inviting guests into the home.

Home in New Buffalo

5 out of 5 average rating, 212 reviews

Designer Cottage - walking distance to downtown

Dream cottage getaway just over an hour from downtown Chicago. Walking distance from the beach, restaurants and all of downtown New Buffalo. Close to the casino, wineries and breweries. Whether driving in or taking the train, The Bradford is a relaxing yet sophisticated getaway. Eat, drink, and enjoy the beach, the pool, the shops and incredible summer sunsets, all within walking distance! Please note pool/bathhouse open late May - September and is shared with our association.Permit C22-0051

Top guest favourite

The exterior of a two-story home is visible, featuring a welcoming front entrance. A large tree provides shade, with a swing hanging from one of its sturdy branches. Ferns line the landscape, creating a natural border around the property, complemented by a well-maintained lawn.

Home in Saint Joseph

5 out of 5 average rating, 95 reviews

4 Bedroom home w/pool in St. Joseph

This home is all about having fun with the family. Open concept kitchen, living room & dining room. Deck off the dining for eating al fresco. Family room & game room area with large screen TV, Nintendo switch, game table with lots of board games & a dart board. Walkout to the pool (unheated) and fire pit area for fun in the sun and evening campfires to roast marshmallows. Outdoor games include bag toss, ladder ball, ring toss. Home is five miles to Silver Beach and downtown Saint Joseph.

Guest favourite

The cozy living area features a comfortable sofa adorned with blue accent pillows and a light armchair. Large windows provide natural light and a view of the outdoor space, while a marble countertop in the nearby kitchen area adds a modern touch.

Tiny home in Sawyer

4.89 out of 5 average rating, 104 reviews

Anchors Away - Sawyer, MI

Welcome to our home! We are so excited to get to share our home with you! Our family-friendly has a cozy living room, fireplace and a full kitchen! On site is a heated pool, laundry mat, and it’s home to the Beach Bucket the best spot for amazing ice cream, homemade popcorn and fudge! Directly across the street is Warren Dunes State Park. The 3/4 mile walk, drive or bike ride gets you to the beach for a fun filled day! Climb the dunes, lay in the sand, go for a swim, relax-you’re on vacation!

Guest favourite

An aerial view captures a cluster of chalets arranged around a spacious parking lot near the water's edge. The surrounding landscape features lush greenery and tranquil blue waters, with various outdoor amenities visible, including pools and recreational areas.

Home in Stevensville

4.93 out of 5 average rating, 28 reviews

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!

Top guest favourite

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

Cottage in Union Pier

4.97 out of 5 average rating, 238 reviews

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!

Guest favourite

An aerial view showcases the spacious outdoor area, featuring a blue tennis court adjacent to a rectangular pool surrounded by lounge chairs. Lush greenery and trees frame the property, while a well-maintained lawn offers additional recreational space.

Villa in Niles

4.97 out of 5 average rating, 131 reviews

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.

Guest favourite

An inviting pool area is surrounded by a wooden deck, featuring comfortable seating arrangements and a large red umbrella providing shade. Lush greenery stands tall in the background, complementing the serene atmosphere of the private fenced space.

Home in Lakeside

4.97 out of 5 average rating, 92 reviews

Lakeside with heated pool & pvt beach access!

LAKESIDE COTTAGE - POOL, HOT TUB & RARE semi-private Lake Michigan access to gorgeous beach shared by just 10 homes, so it’s never crowded! Beach access is a 7-min walk away (no parking). A few 3-4 night stays available this JUNE & JULY! Charming, sun-filled cottage sleeps 8 (3BR + pull-out). Heated 85 degree pool (May 22–Sept 15), hot tub, fire pit, gas fireplace, spacious deck, bluestone patio & grill. 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!

Guest favourite

Home in New Buffalo

4.93 out of 5 average rating, 132 reviews

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 open 5/20 to 9/20 and hot tub. Property on 3 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 3 acre property, this home and 1 guest home ( rented separately) .

Superhost

A private heated saltwater pool is surrounded by a fenced area, featuring chaise lounges for relaxation. Lush greenery is visible in the background, offering a tranquil wooded setting. The pool area is designed for peaceful enjoyment in a natural environment.

Home in Union Pier

4.83 out of 5 average rating, 6 reviews

Two Oaks Cabin Retreat

Escape to this secluded Union Pier retreat with a private heated saltwater pool, relaxing hot tub, and a quiet wooded setting just five minutes from Townline Beach. Enjoy a screened porch for morning coffee, a cozy living area with a wood-burning fireplace, and three comfortable bedrooms. Perfect for laid-back lake living, this home offers the ideal blend of comfort, privacy, and easy Harbor Country fun.

Guest favourite

A clear, blue heated pool is surrounded by a wooden deck, featuring a diving board and a water slide. A storage shed is visible in the background, with a life preserver mounted on the wall, under a canopy of trees.

Cabin in Benton Harbor

4.91 out of 5 average rating, 386 reviews

50 Private Acres w/ Trails & Pool: Cozy Cabin

Unwind in this freshly renovated cabin set on 50 acres of peaceful nature. Explore private walking trails, relax by two serene ponds, or cool off in the seasonal pool (shared with our family). The space includes a kitchen for cooking, Xbox One for movie nights, and a fire pit perfect for stargazing. Dog-friendly and ideal for a quiet escape into the outdoors—with all the comforts of home.