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.

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Guest favorite

Guesthouse in Valparaiso

4.96 out of 5 average rating, 161 reviews

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 mandatory. Pricing on club website. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental. Fresh baked muffins are available in the morning.

Jun 24 – Jul 1

G$13,164 GYD per night

Guest favorite

Home in Lakeside

4.95 out of 5 average rating, 44 reviews

Cottage in Lakeside w/ pool & year round hot tub!

CHARMING COTTAGE W/ MODERN UPDATES IN HARBOR COUNTRY W/HEATED 85 DEGREE POOL (MEMORIAL DAY - MID SEPT) HOT TUB, FIREPIT & PRIVATE BEACH ACCESS IS A 7 MIN WALK AWAY! 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 WITH DIRECT ACCESS TO DECK, BLUESTONE PATIO & GRILL. THE LOCATION COULDN'T BE BETTER - 15 MIN TO WINERIES, 5 - 10 MINS TO NEW BUFFALO & WARREN DUNES & 5 MINS TO SAWYER!

Feb 11 – 18

G$75,888 GYD per night

Guest favorite

Home in Bridgman

5.0 out of 5 average rating, 59 reviews

Cozy Bungalow near Wineries and Breweries

Enjoy a quiet, peaceful neighborhood while being centrally-located to beaches, wineries, breweries, and restaurants. Five minute drive or easy bike ride to breweries and restaurants in Sawyer, Bridgman, Warren Dunes, and Weko Beach. Three bedroom ranch perfect for your family to relax and have fun. Large fenced in backyard with new in-ground heated pool, grill, solo stove. Close to many wineries, orchards, and local farms too! Check Insta: @Farmhouse_11 **Pool open June to end of September

Oct 3 – 10

G$80,612 GYD per night

Guest favorite

Home in Sawyer

5.0 out of 5 average rating, 7 reviews

Las Moras, 6 Acres & Large Pool

Come and enjoy Nature at Las Moras (“The Berries” in Spanish) with rows of blueberry bushes, watch the deer prance through the front yard, see the wild turkeys in the woods, watch the turtles in the pond as you enjoy the 25x30 salt water heated pool, surrounded by a beautiful forest and flowering shrubs, in a stunning setting. The renovated cottage is in a secluded 6 acres, surrounded by an open land preserve, all of this is close to Downtown Sawyer and Cherry Beach, 90 minutes from Chicago

Sep 30 – Oct 7

G$119,340 GYD per night

Guest favorite

Home in Three Oaks

4.9 out of 5 average rating, 102 reviews

Luxe Life | Heated Pool | Hot Tub| Sleeps 10

Important notes: - Home is in HARBERT by the lakefront, NOT in Three Oaks - Hot tub open all year - Pool closed from October 23, 2023 through Memorial Day 2024 After a day of exploring Lake Michigan, Warren Dunes, or New Buffalo (just a quick 10-minute drive away), 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 cap off the evening around the fire pit while toasting marshmallows.

Nov 10 – 17

G$151,064 GYD per night

Guest favorite

Home in Union Pier

4.83 out of 5 average rating, 115 reviews

Modern 5 bedroom farm home , hot tub , pool

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 . 5 bed , 4 bath , hot tub and gas grille and( pool opens June 6) close to union pier beaches and wine country . Property is nestled in a quaint country road location 1/2 mile off re arrow highway. Room for 10 cars,blue stone patios,ping pong table .

Feb 9 – 16

G$52,054 GYD per night

Guest favorite

Cottage in New Buffalo

4.94 out of 5 average rating, 140 reviews

Perfect Get Away - Private Hot Tub - Lots of Room

Gorgeous, New Buffalo cottage in the heart of New Buffalo. Perfect for families and friends ~ many areas for gathering within the home. Private hot tub off the back screened in porch and only ten steps away from large community pool. Walk to everything in NB - Whittaker is only 2 blocks away. Enjoy close proximity: beach, amazing restaurants in town (Stray Dog, Redamak's, etc.). The private hot tub makes this perfect place for social distancing with Family!

Apr 23 – 30

G$140,560 GYD per night

Guest favorite

Cottage in Union Pier

4.96 out of 5 average rating, 172 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!

Apr 2 – 9

G$119,867 GYD per night

Guest favorite

Guesthouse in Cassopolis

4.97 out of 5 average rating, 100 reviews

2 person cottage with pool and hottub

Come for a relaxing getaway in the country. Cook in our small kitchenette or use our pellet grill or fire pit. Located in a small hobby farm setting with cows, sheep, & chickens roaming the pasture. We also have 3 kittens 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 soak in the hot tub and let the worries of life melt away during your stay.

Aug 13 – 20

G$40,894 GYD per night

Superhost

Guesthouse in Michigan City

4.87 out of 5 average rating, 120 reviews

Lagunitas Coach House in Beachwalk, Lake Michigan

Lagunitas Coach House is a sought after location on the quaint Thomas blvd cul de sac. It is the coach house to Gooch Life. It is the perfect get away spot for a couple or small family wanting to escape to the beautiful beach of Lake Michigan. Lagunitas and Gooch Life share the property but are separate structures. Lagunitas has a private entrance, amenities, and parking. Lagunitas sleeps 6, see pictures for bed configuartion.

Oct 14 – 21

G$38,049 GYD per night

Superhost

Tiny home in Sawyer

4.8 out of 5 average rating, 122 reviews

After Dune Delight

We are located in a small Tiny Home park. Full kitchen, sleep up to 6. Directly across street from Warren Dunes State Park. Wineries, breweries all within easy driving distance. Beach Bucket Ice cream shop next door. Walk and bike back to dunes for free. Come and relax with us! After Dune Delight is unit #18.

Oct 1 – 8

G$32,672 GYD per night

Guest favorite

Cabin in Union Pier

4.92 out of 5 average rating, 100 reviews

Two Oaks Cabin - 3 BRs w/ private pool AND hot tub

Two Oaks Cabin, located in the heart of Harbor Country is a tucked away vacation home located in Union Pier, MI. We believe it is the perfect escape to come here and melt your stress away with the hot tub, pool, and the peaceful surroundings. A trusted space with superhost status, this is the place for you!

Dec 18 – 25

G$119,794 GYD per night