Holiday rentals with a pool in Chikaming Township

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chikaming Township

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

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Guest favourite

Cottage

4.95 out of 5 average rating, 39 reviews

Luxury Cottage with pool; summer will book fast

The madrona cottage is the perfect vacation home. You will fall in love with the cottage and the location, New Buffalo is amazing. The home has 4 full bedrooms and 3.5 baths. It will sleep 8 guests easy. Everything you need to enjoy a nice vacation is included in the place. The cottage has been completely rehabbed with all spaces being brand new. It's has a heated pool and is close to the beach. Relax by the fire or enjoy the game room with a pool table, card table and games. Great for families.

Guest favourite

Home

5 out of 5 average rating, 54 reviews

Guest favorite! Quiet setting w/heated pool & more

Welcome to our SW Michigan retreat! This freshly updated home in a quiet country setting feels far away from it all but is close to everything Harbor Country has to offer including beaches, dunes, breweries & shopping. With 5 bedrooms & 3.5 baths, there's enough space for your large family or multiple families to relax & enjoy plentiful amenities including heated pool (seasonal), hot tub, trampoline, fire pit, large yard, multiple outdoor dining areas, woods with paved walking path, WiFi & more!

Guest favourite

Home

4.99 out of 5 average rating, 190 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

4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

Open-concept home with a private heated pool. Take a hike, climb a dune & run back down to the lakeshore in downtown Chesterton, a perfect getaway weekend at the Indiana Dunes. Fenced yard, grill, and cozy fire pit. Local markets, festivals, orchards, and farms. Just a few miles from the beach and national park. Saturday's European Market offers a wonderful healthy, fun, entertaining shopping & dining experience for all. Fresh produce, food trucks, mimosa brunches, and candy shops.

Guest favourite

Guest house

4.9 out of 5 average rating, 758 reviews

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

Hot tub is open! The Pool Barn offers a great location & unique experience. 1 hour from Chicago & less than 10 minutes from large sand beaches & hiking trails of Indiana Dunes National Park & Indiana Dunes State Park. Lots to do at the 'Pool Barn' too. Outside is pool, hot tub, grill, firepit, playground, & we are on hike/bike trail. Inside is billiards, ping pong, air hockey, darts, popashot, foosball, board games, large smart tv, 6 beds, couch, & full kitchen. No cleaning fee!

Guest favourite

Home

5 out of 5 average rating, 33 reviews

Private! Cherry Beach Pool House

2025 Summer Calendar Open! 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!

Guest favourite

Home

4.96 out of 5 average rating, 24 reviews

Poolside Oasis - Private Heated Pool + Fun Games

Escape to our stunning 4-bed, 1.5-bath home with a private in-ground pool! Bright living spaces, a fully equipped kitchen, cozy bedrooms, and an amazing pool await. Conveniently located near charming Saint Joseph, Michigan, with Lake Michigan's sandy shores and vibrant downtown nearby. Indulge in local cuisine, explore nature trails, then return to the comfort of our inviting home. Your ultimate vacation experience awaits! Book now for an unforgettable getaway!

Guest favourite

Cottage

4.96 out of 5 average rating, 192 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, pool, 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 and create lasting memories!

Guest favourite

Cottage

4.96 out of 5 average rating, 103 reviews

Casa Playa New House w/ Private Spa & Pool Access

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!

Superhost

Home

5 out of 5 average rating, 4 reviews

The Poolside Escape | Hot Tub | Arcade | Ping Pong

Discover The Poolside Escape Discover a beautifully renovated single-story ranch with a finished basement, just minutes from Southwest Michigan’s best beaches, state parks, and wineries. Perfect for families or friends, The Poolside Escape offers modern amenities, including a private pool, hot tub, and entertainment options, to make your getaway truly unforgettable. Pool open Memorial Day to September 15th

Guest favourite

Home

5 out of 5 average rating, 23 reviews

The Summer House - Heated Pool - Steps to Sawyer

Welcome to the Summer House! Our newly renovated private home featuring a heated pool is located steps to downtown Sawyer; just a 3 minute drive to Warren Dunes State Park. Enjoy all Harbor Country has to offer while staying in your own home walking distance to coffee, restaurants, and shops! Guest will have access to a private gated pool and parking right in front of the house for four vehicles.

Superhost

Home

4.75 out of 5 average rating, 4 reviews

New Buffalo Pool/Hot-tub/Firepit

Your family will be close to everything when you stay at this centrally-located place. This five bedroom 3 bath home has it all including pool, hot-tub, firepit, fenced yard. Steps from a the association beach (small beach currently) walking distance to the large public beach, town, and marina. Renovated in 2023.