
Holiday rentals with a pool in Chikaming Township
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Top-rated rentals with a pool in Chikaming Township
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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!

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

Private! Cherry Beach Pool House
Summer 2026 Calendar Open! A few weeks left! Get away to Harbor County on this private ¾ acre, open concept home two blocks from Cherry Beach with a large PRIVATE heated pool and hot tub! This home has an open floor plan with natural light filling the spacious living areas. Relax in the 3 seasons room or go for a swim in a ‘15x45’ heated saltwater pool, soak in the hot tub, or roast marshmallows by firepit. New - Universal EV charger. Check our NEW listing - Warren Woods Pool Retreat

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!

Quiet Couples' Retreat, Stock Tank Pool, Nature
Escape to you own private sanctuary in the heart of Michigan's beautiful countryside--surrounded by trees, birds, and wildlife. Leave the noise behind and reconnect in this romantic setting. Imagine sunning in our little stock tank pool, reading a book, or enjoying a cool drink. It is the perfect place for some serious soul care. Or visit the 45 minutes away touristy locations.....Amish Country Shipshewana, Lake Michigan, or Wine Country. Then, come back and enjoy the peace and quiet.

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.

Wabi Sabi Chic at The Flamingo Ranch in Lakeside
SUMMER IS BOOKING FAST at Flamingo Ranch—an unforgettable retreat nestled in Harbor Country, 1/2 mile from the lake. ONE WEEK RENTALS ONLY DURING SUMMER, FRIDAY CHECK IN. This designer-owned haven offers both deep seclusion + an open-format layout that invites connection, healing + memory-making. Whether you’re gathering with family, reuniting with old friends, or seeking a rejuvenating escape, we deliver an experience that’s as comfortable + stylish as it is energetically charged.

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.

Cottage for two with pool & hot tub!
Come for a relaxing getaway in the country. Cook in our small kitchenette or use our Blackstone or fire pit. Located in a small hobby farm setting with sheep roaming the pasture. We also have a couple cats that claim the pool area as their own. The long driveway and gravel road are perfect for a leisurely stroll to enjoy the great outdoors. Take a swim in the pool or a soak in the hot tub and let the worries of life melt away during your stay.

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) .

Pool Opens May 25! | Hot Tub • Walk to Lake
Set in a quiet, wooded setting, this spacious home is ideal for relaxed getaways in every season. In cooler months, the open floor plan and warm interiors make it easy to gather, unwind, and enjoy time together. As the weather warms, forest views, outdoor spaces, and easy access to the pool and nearby beach invite you to slow down, soak up the sunshine, and enjoy a more laid-back pace.
Popular amenities for Chikaming Township rentals with a pool
House rentals with a pool

Luxury home with pool.

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Private Pool-150 Acres of Nature, Red House

Large, Cozy, Theatre, Pool, Walk to ND Restaurants

Modern Lake House w/ Private Pool near New Buffalo

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Modern Farmhouse - Walk to Downtown, beach & pool!

Perfect Family Getaway!
Condo rentals with a pool

Large 3BR w/ pool and parking - near everything

Union Pier Condo with Association Heated Pool.

Union Pier Condo With Heated Pool.

Amazing Beach Condo with pool and great sunsets!

Perfect Location Condo Pools Walk to all Beach 1.5

Nightingale Dunes - Modern beach town retreat

Sunset Pointe Chalet #32: Beach + Pool+ Sports

New Buffalo Getaway Condo
Other holiday rentals with a pool

Sauna | Hot Tub | Heated Pool | Beach Walk

Updated 3 bdrm house w/ pool near beach & country

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

Home near the lake with an inground pool

Spacious 3-BR/2-BA, Beach Access, Woodsy Getaway

Sandy Feet Retreat

Vino Villa | Cozy Escape near Wineries & Lake

Huge Heated Pool, Hot Tub, Notre Dame + Tiny House
Quick stats about holiday rentals with a pool in Chikaming Township

Total holiday rentals
Explore 110 holiday rentals in Chikaming Township

Nightly prices starting at
Chikaming Township holiday rentals start at $194 AUD per night before taxes and fees

Verified guest reviews
Over 2,300 verified reviews to help you choose

Family-friendly holiday rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
110 of Chikaming Township holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chikaming Township rentals

4.9 Average rating
Chikaming Township stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with an EV charger Chikaming Township
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- Rentals with a fireplace Chikaming Township
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- Rentals with pools Berrien County
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- Rentals with pools United States
- Warren Dunes State Park
- University of Notre Dame
- Museum of Science and Industry
- Washington Park Zoo
- Indiana Dunes State Park
- Silver Beach Carousel
- Potato Creek State Park
- Grand Mere State Park
- 12 Corners Vineyards
- Beachwalk Vacation Rentals
- Benton Harbor St Joseph Ymca
- Woodlands Course at Whittaker
- Four Winds Casino
- Jean Klock Park
- New Buffalo Public Beach
- Van Buren State Park
- Potawatomi Zoo
- Silver Beach Park
- Shady Creek Winery
- Promontory Point
- Weko Beach
- Four Winds Casino
- Frederick C. Robie House
- Dablon Winery and Vineyards





