
Vacation 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

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.

New Buffalo / Union Pier Pool Hot tub 7 Bedroom
Relax with the whole family at this peaceful home with Classic European style meets Lake Michigan! This astonishing turnkey home is the perfect escape from life in the busy city. The home is ideal for entertaining Famliy . 7 bed , 4 bath , hot tub and gas grille , close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off red arrow highway. Room for 10 cars,blue stone patios,ping pong table / game room . Pool open 5/20 to 10-1

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.

Private Cottage in Gated Nudist Community
We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is optional . Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area after payment of grounds fees.

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.

Pool & 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.

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.
Popular amenities for Chikaming Township rentals with a pool
House rentals with a pool

Luxury home with pool.

Las Moras, 6 Acres, and a Large Pool

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!

Pool | Hot Tub | Backyard Oasis | Game Room | Fun
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.

Idyllic New Buffalo Condo: Walk to Beach & Shops!

Amazing Beach Condo with pool and great sunsets!

Perfect Location Condo Pools Walk to all Beach 1.5

New Buffalo Condo with Association Pool and Beach!

Nightingale Dunes - Modern beach town retreat
Other vacation rentals with a pool

Luxe by the Lake - Pool Access - Walk to Beaches

Private Pool, Hot Tub & Outdoor TV

Heated Pool & Pvt Hot Tub

Secluded Pool Playhouse: Hot Tub, Game Room, Fire

Cozy~Well-Curated Home•Private Pool• Dog-friendly!

Huge Heated Pool, Hot Tub, Notre Dame + Tiny House

Cozy convenient home with a pool

The Beachside Harborfront Hideaway
Quick stats about vacation rentals with a pool in Chikaming Township

Total vacation rentals
Explore 110 vacation rentals in Chikaming Township

Nightly prices starting at
Chikaming Township vacation rentals start at €121 per night before taxes and fees

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

Family-friendly vacation rentals
100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
110 of Chikaming Township vacation 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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- Warren Dunes State Park
- University of Notre Dame
- Washington Park Zoo
- Indiana Dunes State Park
- Museum of Science and Industry
- Silver Beach Carousel
- Potato Creek State Park
- 12 Corners Vineyards
- Van Buren State Park
- Beachwalk Vacation Rentals
- Grand Mere State Park
- Shady Creek Winery
- Woodlands Course at Whittaker
- Jean Klock Park
- Four Winds Casino
- New Buffalo Public Beach
- Weko Beach
- Silver Beach Park
- Frederick C. Robie House
- Four Winds Casino
- South Beach
- The Promontory
- Dablon Winery and Vineyards
- Promontory Point





