Dickinson County rentals with pool

We found 13 rentals with pool — enter your dates for availability

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September 2025

October 2025

Explore Dickinson County rentals with pools

Living area. Exact unit will be assigned upon arrival. Views, colors, and decor may vary.

Premier Host

Spacious Room with On-site Dining and Indoor Pool - Ideal for Families

Sleeps 6 · 2 bedrooms · 2 bathrooms

Unit with 2 Double beds. Exact unit will be assigned upon arrival. Views, colors, and decor may vary.

Premier Host

Inviting Lodge with Family-Friendly Amenities - Near Local Attractions

Sleeps 4 · 1 bedroom · 1 bathroom

Unit with King bed. Exact unit will be assigned upon arrival. Views, colors, and decor may vary.

Premier Host

Explore Scenic Overlooks from Charming Ski-in/Ski-out Cabin Near Attractions

Sleeps 5 · 2 bedrooms · 1 bathroom

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Explore Dickinson County rentals with pools

Spacious Room with On-site Dining and Indoor Pool - Ideal for Families

Inviting Lodge with Family-Friendly Amenities - Near Local Attractions

Explore Scenic Overlooks from Charming Ski-in/Ski-out Cabin Near Attractions

Tranquil Cabin Perfect for Adventurous Outdoor Escapes Near Local Attractions

Rustic Lodge w/ Heated Pool & Ski-in/Ski-out Access & Golfing- Perfect Retreat!

Pet-Friendly Room with Indoor Swimming Pool - Ideal for Adventure Seekers

Find spaces that suit your style

Rentals with Pool in Dickinson County

Holiday Rental options in Dickinson County