Hotels with Pool & Resorts in Painter

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Best Painter Hotels with Pool

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

What are some accommodation options with pools in Painter?
Charming Painter Home w/ Chesapeake Bay Views: Offers complimentary high-speed (wired) Internet access, a pool and free self parking. Charming Painter Home w/ Chesapeake Bay Views: Features a snack bar/deli, an indoor pool and buffet. Pet-Friendly Woodsy Gem: 1/4 Mi to Chesapeake Bay: Provides daily, a seasonal outdoor pool and free self parking. Cozy Country Home in the Heart of the Eastern Shore: Offers complimentary wireless Internet access, a pool and kitchens.
What is there to see and do in Painter?
Make a point to visit attractions such as SouthEast Expeditions and North Street Market. Discover sights such as The Blue Crow Antique Mall during your stay.
When is the best time to book a hotel with a pool in Painter?
You may want to consider accommodation that has an outdoor pool if you’re planning to visit Painter in the hottest months of July, August or June, when the average temperature is 24°C. Accommodation with an indoor pool may be what you want if you come to town during the coldest months of January, February or December, when the average temp is 6°C.