Holiday rentals with a pool in Berrien County

Find and book unique homes with a pool on Airbnb

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

Home in Stevensville

4.95 out of 5 average rating, 59 reviews

Bright & Modern Home (Pool open May-Oct 21)

The modern architecture and bright and airy design of the home provides a relaxing, inviting and luxurious space for guests. The home: -is set on an a sandy lot, facing a small private lake -has 3 bedrooms, 3 bathrooms, a den and a loft -has an 8-person hot tub and private pool -is equipped with top of the line kitchenwares -includes outdoor amenities such as kayak, canoe, fire pit, grill, yard games (Jenga and corn hole), etc. -allows pets but must be included in the booking and pay a pet fee

Guest favourite

Home in Lakeside

4.96 out of 5 average rating, 83 reviews

Hot tub open year round and pvt association beach!

POOL IS READY AND HEATED TO 85 DEGREES! (Pool closes Sept 15th). CHARMING COTTAGE W/ MODERN UPDATES IN LAKESIDE WITH HOT TUB & FIREPIT. HOME COMES WITH RARE PRIVATE BEACH ACCESS TO LAKE MICHIGAN. BEACH ACCESS IS A 7 MIN WALK AWAY FROM HOME. SUN-FILLED & FULL OF CHARM, YOU WILL FEEL RIGHT AT HOME THE SECOND YOU WALK IN. SLEEPS 8 GUESTS (3 BEDROOMS & PULL-OUT COUCH) AND COMES WITH A GAS FP, GREAT KITCHEN, BIG DECK, BLUESTONE PATIO & GRILL. 10 MINS TO NEW BUFFALO, WALK TO COFFEE, LUNCH, SHOPS!!

Top guest favourite

Home in New Buffalo

5 out of 5 average rating, 201 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

Guest favourite

Home in St. Joseph

5 out of 5 average rating, 26 reviews

Harbor Shores House with Bunk Beds and Pool!

Escape to a tranquil retreat in this 3 bedroom cottage in Harbor Village, where comfort and convenience await. You'll love being situated in the Harbor Shores neighborhood, where downtown St. Joseph and Benton Harbor’s quaint shops and restaurants are just a short walk or bike ride away. The home enjoys stunning views of the marina and golf course from the front porch and terrace accessible via the master suite. Swim and/ or relax at the pool located steps away - right across the street.

Guest favourite

Home in Three Oaks

4.88 out of 5 average rating, 135 reviews

Harbor Country Charm w Heated Pool Open Til 10/12!

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closes October 10, 2024 through Memorial Day 2025 After a day of exploring the waters of Lake Michigan, Warren Dunes, or nearby wineries, find your sanctuary at Mae's Place. Recharge by soaking in the inviting hot tub, sizzle up a delicious meal on the grill or in the kitchen and end the evening roasting marshmallows around the fire pit or watching an outdoor movie on the pool deck.

Top guest favourite

Cottage in Union Pier

4.96 out of 5 average rating, 220 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!

Luxe

Home in Union Pier

5 out of 5 average rating, 10 reviews

NEW! 1BR Cottage w/ Pool, Firepit, Walk to Beach

Presenting Townie 1 - The Ivy, part of the unique Townie Cottages collection. This newly built lakeside luxury home was designed exclusively by Kate Marker Interiors (recognized by Architectural Digest and Luxe Home). Located in Union Pier, these exquisite cottages blend rustic charm and modern elegance for an unforgettable stay. Immerse yourself in a meticulously curated interior with high-end finishes and chic furnishings, creating a sophisticated yet homey atmosphere.

Guest favourite

Cottage in New Buffalo

4.97 out of 5 average rating, 115 reviews

Casa Playa - Union Pier Home w/ Pool & Private Spa

This 4 bedroom getaway is located in the heart of Harbor Country and is just a 10 minute walk or 3 minute drive to the best beach in Union Pier! Casa Playa has EVERYTHING a vacation house can offer: an association POOL, a private HOT TUB, high speed internet that accommodates many people working from home, a cozy indoor fireplace, an outdoor fire pit, an outdoor deck & grill, 2 smart Tvs, ALL brand new appliances, and games for the whole family!

Guest favourite

Townhouse in St. Joseph

5 out of 5 average rating, 8 reviews

Marina Sunset: Savor Fall Flavors in Saint Joseph

Located in the beautiful beach town of Saint Joseph, Michigan, this brand new waterfront townhome is located within Harbor Shores Resort. The area's natural beauty can be seen throughout several dunes areas and beaches nestled on the southeast corner of Lake Michigan. Enjoy wineries, award winning breweries, and an abundance of restaurants. There are adventures abound with boating, fishing, hiking, and biking all nearby.

Guest favourite

Home in New Buffalo

4.97 out of 5 average rating, 29 reviews

3200 sq New Buffalo Pvt Pool | Hot tub 11 bed 6brm

Peaceful and quiet 6 bdrm 11bed 3 bath retreat, nestled between tall oaks with NEW HEATED 16x32 POOL and HOT TUB. Two great rooms that allows your large group to spread out for your stay. Two minutes from beach and downtown by car, or take a ride on provided bicycles for a 10 minute ride on New Buffalo’s new bike path! Home features HUGE chef’s kitchen and dining area for whole group to gather comfortably in any season .

Guest favourite

Home in Niles

4.92 out of 5 average rating, 107 reviews

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.

Guest favourite

Home in Bridgman

4.99 out of 5 average rating, 88 reviews

Heated Pool | Quiet Area | Huge Fenced Yard

Enjoy a quiet, peaceful neighborhood while being close to everything. Five minute drive to Warren Dunes, Weko beach, wine bars, breweries, and restaurants. Three bedroom ranch perfect for your family to relax and have fun. Large fenced in backyard with gorgeous in-ground heated pool (June-September), gas grill, solo stove. Close to many wineries, orchards, and local farms. Lovely area for bicycling!