Holiday rentals with a pool in Benton Harbor

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Top-rated rentals with a pool in Benton Harbor

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

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Guest favourite

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.

24 Jun – 1 Jul

$120 NZD per night

Superhost

Cabin in Benton Harbor

4.91 out of 5 average rating, 288 reviews

Cozy Cabin by Nature

We deep clean and sanitize after every guest. Enjoy social distancing in this completely renovated cabin in a picturesque setting with 2 ponds. Dog friendly. A full kitchen to cook your own meals. Xbox one is provided to watch movies and relax. Enjoy outdoors with the fire pit. We are dog friendly. We do ask 3 things if you bring your furry family with you. Please keep them off the furniture, clean up after their business and keep them leashed when around other guests as the property is shared

12–19 Jun

$603 NZD per night

Guest favourite

Condo in Douglas

4.97 out of 5 average rating, 149 reviews

Fun bright condo with pool only steps away

Beautifully updated vacation Condo with association pool only steps away. Pool is open early May! Close to Lake Michigan and all of the fun activities Saugatuck-Douglas has to offer. Less than 1 mile to Lake Michigan. Close to Douglas and Oval Beaches. Relax on your own front porch or walk a few steps to Isabel’s, a wonderful eatery right on site. One bedroom one bath with a cozy gas fireplace. Additional sleeping for two on pull out couch in the living room. Close to bike path to downtown.

25 Sep – 2 Oct

$405 NZD per night

Guest favourite

Home in St. Joseph

5.0 out of 5 average rating, 10 reviews

Brand new St Joseph Resort House with POOL

Come enjoy all that Soutwest Michigan has to offer in our stylish new house in the Harbor Village Resort development, within walking distance to St Joseph with boutique shops, kids museum/carousel/splash pad, and beaches! Relax in the stylish decor in this brand new 3 br house. Soak up the sun in the large pool right across the street! The Inn at Harbor Shores Resort is also at your doorstep with golf, a spa, upscale Plank's restaurant/bar, conference center, coffee shop, and marina access.

15–22 Nov

$456 NZD per night

Superhost

Campervan/RV in Porter

4.79 out of 5 average rating, 608 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Hot tub open all year! Fully equipped RV is parked in the driveway of our Pool Barn. RV sleeps 6, has bath w/shower, stove, microwave, heat & A/C, & running water all year. We are located minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hiking in the Indiana Dunes National Park along the Little Calumet River and the historic Bailley homestead is only 1 block away. You may also use our large pool, hot tub, grill, campfire, and playground area. No cleaning fee!

1–8 Feb

$319 NZD per night

Guest favourite

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.

10–17 Nov

$1,359 NZD per night

Guest favourite

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!

23–30 Apr

$1,282 NZD per night

Guest favourite

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!

2–9 Apr

$1,114 NZD per night

Guest favourite

Home in New Buffalo

4.91 out of 5 average rating, 264 reviews

Farmesque with a splash of modern

Turn back time with trough sinks and claw foot tub and cedar beams ,distressed floors and walls with a mix of modern. Galien river marsh across street full of nature and several bikes on property for your riding pleasure . Newly built 2019 , 3 blocks from Main Street downtown New Buffalo.6 blocks from beach , enjoy all local spots and coffee shop and grocery steps away . Dead end street in very quaint neighborhood, covered front porch enclosed rear porch .

3–10 Mar

$455 NZD per night

Guest favourite

Guesthouse in Zeeland

4.95 out of 5 average rating, 241 reviews

Honey Bee Ridge Guest House

Our Guest House is located on a quiet country road 15 minutes from beautiful downtown Holland and 20 minutes from beaches, downtown Grand Rapids and Saugatuck. The property sits on 5 acres with the owners home next to the Private Guesthouse. You'll have access to the pool, your own patio with comfortable seating, and a wood fire pit. A 600 acre park with paved running/biking/cross country ski and mountain biking trails is located across the street.

11–16 Jun

$339 NZD per night

Guest favourite

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.

13–20 Aug

$363 NZD per night

Guest favourite

Home in St. Joseph

4.9 out of 5 average rating, 20 reviews

Updated 3 bdrm house w/ pool near beach & country

Your family will be close to everything when you stay at this centrally-located place. 10 minutes to wineries 10 minutes to Silver Beach 10 minutes to downtown St Joseph 5 minutes to Grand Mere State Park 45 minutes to Notre Dame 90 minutes to Chicago Our house is extremely comfortable for singles, couples, and families. Come relax and enjoy. We have everything you need for a perfect stay.

2–9 May

$413 NZD per night